June 4, 2026

87. The Mindset of Style and How to Like the Way You Look, with Jennifer Mackey Mary

87. The Mindset of Style and How to Like the Way You Look, with Jennifer Mackey Mary
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Do you feel like your body is changing, nothing fits right, and it’s easier to just wear pajama pants with a professional shirt for your Zoom calls? Giving up on getting dressed takes a heavy toll on how we feel about ourselves.

In this episode, I welcome style expert Jennifer Mackey Mary. Jennifer is the founder of Everyday Style and host of the top 10 podcast, The Everyday Style School. We dive into why mindset is the critical first step to style, how to confidently dress a changing midlife body, and why looking good is directly tied to feeling good.

What You’ll Learn:

  • The Real Meaning of Style: Why dressing well doesn't mean dressing up in uncomfortable clothes, and why style matters most when no one else is watching.
  • Dressing Your Changing Shape: How to stop hiding behind oversized fabric, ditch traditional body shape labels, and use clothing elements to highlight what you love.
  • Where Style Actually Starts: Why shopping should be your very last step, and how choosing three words to describe how you want to look can transform your closet.

Episode Chapters:

00:00 - The mindset around style and getting dressed

02:51 - Redefining what dressing well means

08:12 - Why invisibility as we age is a choice

11:58 - How to dress when your body and shape start to change

21:32 - Simple tricks to highlight your waist and hide your tummy

29:00 - The crucial three steps to style before you ever go shopping

36:15 - Building a cohesive wardrobe that feels like you

40:30 - Why life is better when you like the way you look

Links & Resources:

Why This Episode Matters: By changing your style operating system and choosing to show up for yourself, you can start loving your clothes no matter what the tag says. Take a little bit better care of yourself in midlife.


Grab your Vitamin G pixie sticks for detoxification and wellness at cherylpfischer.com/vitaming.

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00:00 - Style Starts In Your Head

01:08 - Meet The Mindset Style Expert

02:41 - Dressing Well Without Dressing Up

05:20 - At Home Clothes That Build Confidence

08:12 - Aging Without Going Invisible

11:41 - Body Changes And The Mind Mirror

17:03 - Highlight What You Love On Purpose

23:12 - Waist Tricks That Actually Work

30:29 - Stop Shopping First Start With Mindset

40:32 - Where To Learn More With Jennifer

42:14 - The One Takeaway And A Challenge

45:26 - Final Wrap Up And Reviews

Style Starts In Your Head

Cheryl Fischer

Okay, riddle me this. You want to feel good about yourself, you want to feel good in your clothes, but oh, you don't want to go shopping, you feel like pants never fit, or maybe you work from home or you're not working anymore, and you don't see why you need to get dressed. Why not just wear pajama pants and whatever professional shirt you need on the top? There's so much mind stuff around style and getting dressed. So let's talk about it. Welcome to Mind Your Midlife, your go-to resource for confidence and success. One thought at a time. Unlike most advice out there, we believe that simply telling you to believe in yourself or change your habits isn't enough to wake up excited about life or feel truly confident in your body. Each week, you'll gain actionable strategies and, oh my goodness, powerful insights to stop feeling stuck and start loving your midlife. This is the Mind Your Midlife podcast.

Meet The Mindset Style Expert

Cheryl Fischer

My guest today first caught my attention when I was listening to her podcast. I was curious because she talks about style, as you might imagine, since that's today's topic. But the difference is she was coming at style from a perspective that mindset is the very first piece. And can you imagine it? I love that. So the idea being it's about how we feel about how we look that is the real power of any style decision, any style concern, always. And that's powerful. So Jennifer Mackey Mary is joining me today on the podcast, and she helps women have easier mornings and better days. Her business is called Everyday Style, and she's on a mission to inspire women to love the way they look and give them the tools to make style easy. She's the host of the top 10 podcasts, the everyday style school, and she says that is about teaching us everything that our moms never did about getting dressed. I am so excited to have this conversation. And I'm gonna also say make sure you listen all the way to the end because she is giving some amazing tips all the way to the end. Welcome, Jennifer. Thanks for joining me. Thank

Dressing Well Without Dressing Up

Cheryl Fischer

you so much for having me. We're talking about women in our 40s and 50s, maybe 60s. Is it a big deal that we actually get dressed every day?

Jennifer Mackey Mary

Yeah, I think it's really important that we get dressed every day. But I think what's important to really understand is that dressing well doesn't mean dressing up. And I think for a lot of women, this is where it falls apart. Because we go, well, I don't go to the office five days a week. I don't go anywhere special, I don't see anyone. Why does it matter? And we think that in order to dress well, that involves uncomfortable, impractical shoes. It involves pants with like real zippers and buttons and waistbands. And it doesn't have to mean that. Dressing well to me means that I am dressed appropriately for my day in a way that makes me happy. There has to be this marriage of form and function. And the reality is we will always default to function. I am never, ever, ever going to choose a blazer when I could wear a sweatshirt. That's just me. That's my style. I like to be comfortable. But so that means I have really cute sweatshirts. I have sweatshirts that fit well. I have sweatshirts that are in good condition. My jeans are not boring and trumpy. So I think we just need to redefine what getting dressed means and what dressing well means. And the reality is, does it matter? Does it really matter what you wear? No. As a wardrobe stylist who tells people all day, every day it matters. It doesn't to other people. It matters to us because when we feel good, we show up differently. When you, you know, I was at the gym this morning and I actually really liked my gym outfit. And I caught a glimpse of myself in the mirror. And I was like, oh, she's cute. And I could remember times where I haven't liked my gym outfit. And I catch a glimpse of myself in the mirror and I think, why am I here? Why bother? I'll never have the body I had when I was 25, 30, 35, 40, right? And that's unattainable. Maybe I should just go home and drive through McDonald's on the way. So it doesn't. It absolutely does not matter what you wear. The people who love you and care about you and respect you, they're still going to do those things. It matters to us how we show up. That's what matters. So we just have to reframe what does getting dressed mean? And what does dressing well mean and why do we do it?

Cheryl Fischer

It's

At Home Clothes That Build Confidence

Cheryl Fischer

really fascinating because I work from home and I mean so many people do nowadays in like the stretchy pants or the pajama pants while putting on the business shirt on top. And so what you're saying is it's a question of how we feel. That's right. That's right.

Jennifer Mackey Mary

Frankly, all of my dress pants are more comfortable than jeans. There are so many pieces out there that are comfortable, that are polished, that look nice, that you don't have to feel like you're in your flannel pajama pants on the bottom and a blazer on top. When I have done that, and I have done that, I'll be the first to admit, I feel like a fraud, right? I feel like I have this secret. And the secret is I'm not worth paying me, or I'm not, I'm not good at what I do. Like it's not a secret against them, it's a secret against myself. So why not sit here in dress pants that are so comfortable that I could go take a nap in, that I could go walk my dog in. And then there is no secret. There is no secret shame of I don't have my stuff together because I do. I'm just really comfortable when I do it. We do not have to choose anymore between looking polished and feeling put, you know, feeling comfortable. We don't have to choose that. And I remember this article I read after the pandemic, and it was about kind of putting yourself back together for working at home. And the article had these, I guess, wool trousers, wool kind of herringbone trousers, and these $700 loafers. And I was just, oh, no, no. Right. This year I bought really cute UG slippers that I could that I can go to the mailbox in, that I can go outside with my dog, whatever. I bought those and they elevated my at-home everyday style. You do not have to sit here being frumpy-dumpy, waiting for an occasion to go somewhere. And that is really, to me, the true meaning of style is that I have style when it doesn't matter to anyone else. I have style when I'm not expected to dress up. It's just what I do. It's not a thing that I put on when it quote unquote matters. Because as life changes and it matters less and less, that's when we stop doing it. And, you know, I think that really takes a toll on women, especially in this age group. It really takes a toll. You stop feeling like a person.

Cheryl Fischer

Mm-hmm. Well, there's a lot of messages out there. We're not desirable anymore, or we might as well give up, or we're gonna wear the grandma outfit, or whatever it is. So I can see what you're saying. If we're kind of sitting around in our slumpy stuff, it's gonna be magnified.

Aging Without Going Invisible

Jennifer Mackey Mary

Absolutely. I remember my mom saying to me the entire time I was growing up, well, you hit a certain age and you become invisible. You hit a certain age and you become invisible. And I remember, even from a young age, thinking, not me, I'm not doing that. And when I went to work for Chicos, I was in my early mid-20s. I think I was 25. And I had all these women who were in their 70s and 80s coming in and wanting like the metallic, sparkly jackets, and those women were not invisible. They were not invisible. And I just I believe, and this is going to be controversial, and I'm sorry, ladies, invisibility is a choice. That is 100% a choice. I choose as I age to lean more into what I like and who I am. Because isn't the beautiful thing about aging that we don't have to care what anybody else thinks? I mean, that's that's supposed to be the payoff, right? So, what's the benefit of that benefit if then we're like, but don't look at me because I've aged. Okay, I've aged. And you know what? Now I can afford better clothes than I could when I was 20. You know, and I know that's a good idea. Yeah, there's more fabric, there's definitely more fabric, but I have nicer things. I have, I have honed my personal style. I can look at something and say, yes, I love that. No, I don't. Like there is joy in that. And if we just give that over because maybe we like a little bit more elastic in our pants, or maybe we're not clubbing all the time, I think that's really sad. And I I, you know, I have teenagers and they help keep me young because I am aware of what is trending. I am aware of what music is happening. But one thing I've decided not to do is ask them for help with technology anymore because I realized that was a place that I was checking out, right? And saying, Well, I'm old, it doesn't apply to me anymore. Oh no, it does. It absolutely does. So go take your old butt in there and figure it out. Figure it out. It is harder to stay relevant. But really, these things are somewhat of a choice. And yes, are we fighting against society saying that, you know, youth is beautiful and this is the you think about actresses. I don't know any actresses that are my age anymore. I don't I look at movies and I'm like, who is that? I don't even know. So there is that, but there is so much of that that we can just choose not to participate in, not give in to, and just say, no, this is this can be my prime time. Yeah. I couldn't possibly agree with you more. It is a choice, it is. It's an uncomfortable truth. It really is. I saw this thing once or read something, and it said, Don't let the old lady move in. Because when you let the old lady move in, she lives there, she lives there. And it was the day before I saw that, the day before I took my daughter to a standing room only concert. And the entire time I'm driving this concert, I was like, I don't want to go. I like to sit down, I like to be home by nine o'clock. And I thought, do not let the old lady move in. And that concert was the most fun I had all year. So it's just a choice.

Cheryl Fischer

It's a choice. It's a choice, absolutely.

Body Changes And The Mind Mirror

Cheryl Fischer

And at the same time, we might get to this period of life and our bodies start to change, maybe our shape starts to change, and that feels hard. And it's hard to adjust and figure out, well, how am I supposed to dress now?

Jennifer Mackey Mary

So I think what's important to realize is that for the most part, when we're talking about these traditional sort of body shape labels, most women's don't change. Our bodies change, yes, but our shape doesn't really change. For example, I am bigger on top than I am on the bottom. If I grab a medium in a top, I'm probably grabbing a small in the bottoms. That's been my shape. It was true when I was buying extra larges and larges or smalls and, you know, the it that doesn't really change. The distribution of things changes, and that can feel like a like just like your world blew up and you don't know what exactly you're doing. And I think one of the biggest things women do is they say, okay, now I have a thicker middle, I'm not quite as curvy. I just want big clothes that cover everything up. And that has never, ever, ever been a winning strategy, and it never, ever, ever will be a winning strategy. So we have to sort of adjust a little bit, right? If you are used to having this hourglass figure and now it's it's still an hourglass, but not quite the same proportions, don't start dressing it like you've never had a curve in your life because you're going to be very unhappy with that. Very unhappy with that. If you were a size four hourglass and now you're a size 12 hourglass, you're still an hourglass. And all the things that worked before still work. And what happens is that a lot of women start shopping with their mind mirror instead of the actual mirror. And your mind mirror is a lying liar who lies. She never tells you good things, never, unless you've had a couple drinks. And she's like, everything you do is wonderful and you are beautiful, right? But for the most part, your mind mirror, she lies to you. And I have had so many women when we would work together in their closets, I'd say, okay, try these jeans. Oh, those don't fit. Those don't fit. And I'd say, Well, try them on anyway. Oh, they fit. Mm-hmm. Yes. Because the five pounds you gained did not turn you into Ursula the Sea Witch from the Mermaid, right? That's not what happened here. But we let that mind take over and we stop looking at ourselves and we stop understanding our bodies. And that to me is the biggest thing. And I see so many women just, I'm just gonna cover it all up with fabric and more fabric. It doesn't work. It really doesn't work. You still have to highlight the parts you like and cleverly dress the parts you don't. But the way I teach body shape ditches those labels completely. Because the truth is, body shape is really just about understanding your body, you know, which parts are bigger, which parts are smaller, which parts are curvier, and then setting goals. So for my goals, it could be I want to balance my upper body and lower body, right? I want my lower body to look the same size as my upper body. And then what do you want to do with your curves? And then, and this is true if you're using my way or the label way. It is about using elements of clothing to achieve those goals. What things will help me look a little smaller on the top, a little bigger on the bottom? What things will help highlight a waist or camouflage the fact that I don't have one? Which things will draw attention to my neckline or what? And the elements and what those things do never, ever, ever changes. So I think for a long time, what we have done is we've said, okay, take a quiz, here you go. Now you have your body shape. Here's your must-have, wear this, where not, that that list. And then that stops working for you. And then you think, oh, well, now I have to start totally from scratch. And that's not true. When your body changes, you say, okay, I no longer want to draw attention here. So now I'm going to use those elements that help hide this instead of highlight it. And it's just a different way of understanding bodies and understanding what clothes do. So if I had a dollar for every time I've been asked, can a blank wear blank? Right? Can an apple wear a bomber jacket or can a pair wear skinny jeans? Whatever it is, I would own island somewhere because that is what women are so obsessed with. But my a better question is, what will this do for me? So I like that. Can an apple wear a mock turtleneck? This is one of my very worst styles, right? Sure, I can. Can I put it on my body? Yeah. Am I gonna like the way I look at it? No, because what it's gonna do for me is it's going to make my neck look even shorter. So yeah, I can wear it, but I'm not gonna like the way I look in it. Right. So can you wear it? Of course, if you could put it on your body, you can wear it. But are you gonna like the way you look at it? No, and that has to do with what will it do for you? And that comes back to understanding your body and your goals and just using clothes to match that. It really doesn't have to be any more magical, mystical, complicated than

Highlight What You Love On Purpose

Jennifer Mackey Mary

that.

Cheryl Fischer

Yeah. I really like that because I'm not even sure that many of us sit down and think about what parts of our body we want to highlight. I mean, we just spend time criticizing all parts, not saying this is the part I really want people to notice. And even just that is a better way of looking at it already.

Jennifer Mackey Mary

Yes. So I do a a body shape analysis uh service, and I started doing this because so many women don't look at their bodies. Because I'll say, you know, what's your shape? I don't know. Well, just look. Well, is there like an online calculator? No, just just like look, look in the mirror, just tell me a bigger topic. And they don't want to do it. They don't want to do it. And then when they do, it it's it all they can focus on is the parts they hate. And I do think traditional body shape advice comes from the place of let's fix what's wrong with you. Yeah, there's nothing wrong with you, there's nothing wrong with your body, there's nothing wrong with your body shape. Show me a body and I will show you easier things to dress on her than someone else. I will show you harder things. I mean, even everyone says, Oh, if I were an hourglass, it would just be so much easier. No, those women struggle so hard to find clothes that fit everything, all fit issues are just highlighted for hourglass women. But we think that's just the ideal. We think it's the ideal. But one of the questions that I ask in this analysis form is which parts would you like to highlight?

Cheryl Fischer

Yeah.

Jennifer Mackey Mary

And which parts would you like to camouflage? And I had to add a little part to the form that says, if you say all to which parts would you like to to camouflage, and none to which parts would you like to highlight, I won't do your analysis because that I that's it. I'm not doing it. Because that is all I was getting. Which parts would you like to highlight? None. Fun. Great. Which parts would you like to camouflage? All oh my goodness. Okay, here's a moo-boo, we're done. Right, exactly. So you can see how then we end up just in head to toe, too much fabric. It's just a cycle that starts in our head that there's nothing good about our bodies anymore. And that's just not true. And and even if you can't say, I just really want to celebrate my butt or my shoulders, I tell people, okay, just imagine you walk into a Starbucks, right? You walk into a Starbucks, you walk into something. People naturally look up when someone walks into a room, right? Not in a judgy way, it's just, oh their eyes are gonna go to something, what would you like them to go to? And when I ask it that way, people usually go, Oh, I I guess my shoulders or my face or, you know, my legs, whatever. Like it's an easier question than what would you like to highlight or celebrate? Just if someone's eyes have to go somewhere, where would you like them to go?

Cheryl Fischer

Now, how would you handle it if someone said to that, my hair or my face or my eyes? That's not, you know, if if those are those are parts we're not really dressing in the same way.

Jennifer Mackey Mary

Well, we are dressing them. We are dressing them with glasses and hair color and accessories and earrings and and necklines that draw the eye up and shoulder details. We can put lots of we can put lots of focus right here. Plenty of focus that nobody really ever has to. I mean, we can a bright red lip makes your hips look so much smaller, right? Because no one's looking at your hips anymore. You know, if someone came in with crazy hair and wild makeup and you said, what size do you think she was? People would say, I don't know, I didn't get that far, right? So that's what's memorable. So whatever it is, find something. Find something, but you cannot go through life just wanting no one to look at you and still participate in life. That's not how it works.

Cheryl Fischer

Yeah, such a powerful point. I do find it so much easier to critique versus decide this is what I want to show. Absolutely. I know there is someone listening right now who is thinking to themselves, that's all well and good, but I need to know what will highlight my waist and make it look smaller. So is there a simple answer to that or is it more complicated?

Jennifer Mackey Mary

Well, it's simple and complicated. So I will give you the very short version. And it's funny, this seems to be the question that I am getting all the time lately. I don't know. The universe will send me just the same question over and over and over for two months and then it's on to something else. Okay, if I said to you she has a 30 inch waist, is she curvy?

Cheryl Fischer

Well, I guess I don't know, right? I don't know. Why don't you mouth? You don't know.

Jennifer Mackey Mary

I don't Your waist is not big or is not small on its own. Now, if I say that 30-inch waisted woman has a bust of 32 and hips of 32, is she curvy? No. Bust of 42, hips

Waist Tricks That Actually Work

Jennifer Mackey Mary

of 42, is she curvy? Heck yeah. So in order to make your waist look smaller, you need to have volume above and volume below. That's it. So a lot of women, and I think I don't have my candle with my rubber band anymore, but last week in style coaching and my membership, someone was asking why I put a belt on this to look like I have a waist. A horizontal line does not create a waste. And we, I mean, that just probably blows things that women have always felt for, well, I'll just put a belt on it and then I'll have a waste. It doesn't. So if you take your diet coke can or whatever you have near you and you just put a rubber band around it, it doesn't all of a sudden turn into a Coke bottle, right? In order to do that, we would need so many times. I know every woman has because that's part of just this just it's unthinking style advice. It's unthinking style advice. It just in the end makes women feel bad. So let's stop doing that. You have to have something above and something below. So if you had a dress with lots of volume and then you put a belt over it, would that make someone look curvier? Absolutely it would, because you have volume above and volume below. So just on its own, you can't just slap a belt over something and think it's going to give you a waist. Now there are other ways to do it. You can belt underneath, like a third piece, a ja an open jacket, an open cardigan, because then what you see is the the evenness on the side, but a focal point right in the middle. That's a great way to hide the stuff women want to hide, but still kind of have that illusion of a focal point right in the middle that draws the eye in. But yeah, absolutely we can we can do all those things.

Cheryl Fischer

I think the waist thing is very particularly a midlife thing. All the menopause, perimenopause stuff going on. A lot of times it feels like that's where the weight is going. Yeah. So that is great advice. Yeah. And now I understand why I've been given the advice to wear like jeans and a blazer and wear a belt underneath. I've also put a belt over a dress and I hate it every time I do it. And so now I see why.

Jennifer Mackey Mary

But there are some incredible dresses. So the other thing that has been coming at me, like gangbusters lately, is how do I hide highlight my waist and hide my tummy? And I know there are thousands of women listening right now going, yes, that's my problem. And that one is a little more challenging, right? That one is a little more challenging. It's like, look at it, don't look at it. My dog has this game he plays, and I call it drum my bone, don't touch my bone, because he wants you to throw this thing so badly, but you're also not allowed to touch it. And that's just like the paradox of highlighting your waist while not looking at your midsection. But this season, spring summer 2026, has given women, I think, of our generation a gift, a wonderful gift with all of these wrap style tops, even things like the corseted sort of, and when I say corseted, I'm gonna say it, then I'll explain what I mean. The style dresses that are just shaped through the waist. I'm seeing that they're like shirt dresses, right? But they have this wonderful seaming through the midsection. And it gives such a beautiful shape. And I'm seeing them in like short sleeve blouses. There are so many waist tie t-shirts and waist tie. And I'm not talking about the little bunny ears, you know, at the at the waist or, you know, like that hang low. Not talking about that. I'm talking about right on the waist. They are back, ruching through the midsection is back. It is the biggest gift to women who want to show curves and hide their tummies. It's here you go, stock up, stock up. I love it. I need to go to the mall and I need to look and see what you're talking about. And also woven fabrics like a dress shirt, those hide things, right? Knits like a t-shirt, they cling and they show things off. So you can have a shirt like it, the woven kind of dress shirt. But for a lot of women who have any kind of curve, they feel very straight, very boxy. It's not a good feeling, right? So this gives that the fabric that you need, that structure that doesn't cling, but it gives you the shape. And then with the T's and things like that, it still has that nice, comfy, drapey knit, but it just has a little bit of shape, of detail that doesn't cling really hard. The truth is you highlight a waist horizontally. So if you are somebody who is that hourglass, traditional hourglass shape, and you want to show that off, you show that off with a belt. You create a waist vertically and diagonally. Think about it. Wrap dresses. Wrap dresses are just ubiquitous for creating that curve, that shape. What are they using? They're using those diagonal lines. When you look at corseting, what is it using? It's using those vertical lines. So it's really just how do we want, where do we put the lines? How do we want them to go? Where is the eye traveling? But right now there are so, so many tops that are easy. I'll tell you, I was online, I was with a client earlier today, shopping online together, and there is, it's just like a t-shirt at Old Navy, and it has this little ruching on the sides. And that is so genius because a lot of times when we put a t-shirt on, we have the tendency to pull it straight down. And all that does is create a huge expanse of fabric completely unbroken, and that's just where your eye goes. But this little like ruching and shearing, it creates these little folds of fabric across it that break up the fabric. It kind of moves the eye around, highlights the curves, hides the tummy. Genius. Wow. Yeah. It's like $22. I mean, yeah. It they're magic, though. They are absolute magic. Okay. To old navy, we all go. Yeah, right. Or you can invest more, but that's just the one I found today. But they're everywhere. Yeah.

Cheryl Fischer

Yeah. That's that's a great tip. Okay. So let's say someone is listening and they're thinking, well, I want to try, but I've no idea what to do. Or do you have some tips for getting started on on trying to dress in a style that's better for you or trying to feel good? Absolutely.

Jennifer Mackey Mary

So in my membership, something I teach is where style starts. Because if I ask all of your listeners a question, when you want better style, where do you start? Where do what do you do? The answer, 99.9% of the time, is going to be I go shopping.

Cheryl Fischer

Mm-hmm.

Jennifer Mackey Mary

That's what I was thinking. Right. No, that is the last step in style. That being the first step is the reason you have a closet full of clothes and nothing to wear. It's the reason you are standing in a fitting room, frustrated, crying, thinking your body is

Stop Shopping First Start With Mindset

Jennifer Mackey Mary

the problem. That is the problem right there. So what do we do? We start with mindset. We start with mindset and we start with why does this matter to you at all? Why does this matter? You know, I grew up with a mom who dressed incredibly well when she was thin. That's it. When she was not thin, she barely wore makeup. She wore oversized, just frumpy, frumpy, frumpy things. But when she was thin, she had the most amazing wardrobe. And watching that, I chose a different path. I chose a different path because I want my teenage daughters to see me loving my clothes and loving my style and loving the way I look, no matter what the tag says. I think that is the biggest gift I can give them. But the problem is we don't even think about what we think about style, right? We don't think about it. And until you do that, all of those thoughts, all of those programmed instincts, I call it your style operating system. Your mind is your operating system. It is running in the background all the time, making all the decisions for you. That's in charge. So you got to choose, you have to install a better operating system. One that says, I matter. The way I am today matters. Good clothes, I am worth it. I am worth good jeans. My daughter can pay for her own Starbucks because I want the good jeans, right? That's okay to say. It really is. And once you have your mindset right, because I'll tell you, there is nothing you can buy. There is nothing you can buy that will overcome I'm not worth it and it doesn't matter. Nothing. Yes. And you will go to the store and what you will buy are clothes that you hope will motivate you to want to dress better. They don't. The clothes are not motivation at all. It doesn't do anything for you. It just mocks you in the morning, but it doesn't, you know, motivate you during the day. So once we have our mind right, then we decide how do we want to look? What is our style? This is also something women have never thought about. Very true. Never. You know the book Seven Habits of Highly Effective People. Number two is begin with the end in mind. I think it's number two. So real quick, let's say I invite you over for a girl's painting night, right? And I say you can paint anything you want. You are going to paint the kind of day you had. You had a wonderful day. You're gonna paint fun flowers, you're gonna paint puppies and rainbows and kittens and whatever. You had a bad day, you're using grays and blacks and whatever. And now you go, oh, this is a beautiful painting. And I say, Great, now hang it above your bed. You would say, Well, wait a second. Had I known that, I would have chose a different color, I would have chose a different size, a different landscape, I would have done, I would have made different decisions to end up with something I could use. So I encourage women just pick three words that describe how you want to look. Look. Comfortable is not a looking word. If someone walks up to you and says, you look so comfortable, that is not a compliment. No, it is not. You want to feel comfortable and by all means, I am the queen of comfort. I am never not comfortable, ever. Life's too short, right? But I never look comfortable, ever. That would be such an insult. So choose three words that describe how you want to look. Then you can use those words when you shop, when you put outfits together, when you edit your closet. Half of that stuff that you're hanging on to for someday, you don't really know what's wrong with it. It's just not your style. Just not your style. You're not gonna wear it. You're not, there's never gonna come a day where you're like, yeah, I kind of want to wear something that is not my personality, not my look. It makes me feel bad about myself. There's not, it's not gonna come. Yeah. So once you do that, then you learn how to dress your body. You understand your body, you set your body goals, you understand the elements of clothing. Then you can shop. Then you can shop. But until you've done those three things, it is just more trial and error that it's just really more error.

Cheryl Fischer

That makes a lot of sense to me. And I'll think about my words because I don't know what they are necessarily off the top of my head. But if I just make up an example and I say one of my words is sophisticated, I could see how I could go into my closet and hold things up even or try them on and say, does this make me look sophisticated?

Jennifer Mackey Mary

And here's kind of next level. I call them style guideposts. You should be able to apply these style guideposts. Mine are current, polished, and fun. Everything I buy, everything I like my overall wardrobe needs to hit at least a couple of them. Because a white t-shirt is a current polished. Sure, is it fun? Uh-oh. It's a white t-shirt, but you need it in your wardrobe, right? But you need to be able to apply your words to pajamas and an evening gown. Oh. Because what happens is women say, Well, I'm this way and this way, and I'm this way when I'm here, and what I wear at home doesn't matter. And actually, it matters the most. What you wear when no one sees you matters more than anything because that is a direct reflection of how you feel about yourself and your worthiness. So those things matter most. My pajamas are current, polished and fun. Love it. I have current polished and fun sweatshirts. I have current polished and fun blazers. You can you can apply that to absolutely if I had anywhere to go in an evening gown, it could be current, polished and fun. And if you can't apply those words, if the words don't make sense grammatically, you know, I I my style is machine washable. That doesn't no, it's not. It's not. You can absolutely want and have machine washable things, but that's not your style. Choose how you want to look and then make that happen. But it is such a good North Star for not buying things because when we go shopping first, we buy things we think we should have or what stylish woman women would wear. And they're not usually a reflection of who we are or how we live. And then you just have more things you don't want to wear. And that we go, I know every woman's got plenty of those. I know.

Cheryl Fischer

Oh, for sure. For sure.

Jennifer Mackey Mary

But imagine imagine if you opened your closet and everything in there you were excited about.

Cheryl Fischer

I I love this concept because actually I've heard about this on your podcast before, and we don't have time to go down this other topic. But what has helped me with that is knowing my season, my color season, because everything goes together then. If it's all in the same season, I put on whatever with whatever. So I can see that having this focus on how do I want to look. And these are my words.

Jennifer Mackey Mary

This is just another way of making that cohesiveness. Because if I buy fun pants and then I buy really classic, elegant, sophisticated tops, there's a disconnect. And I I remember saying to lots of clients, who lives in your closet? Because the these tops are going one place and these pants are going another, right? These are different women. So we need to, we need to make all the parts of our wardrobe be the same woman. So then they just sort of all naturally start to go together. And you know, there's a lot of there's a lot of nuance in the whole capsule concept and mix and match and all that, but it's just a way to start to make it cohesive and you start to see, oh, okay, I could wear this with this, and I've got I I have more options. But the most important thing is everything feels like you. Everything feels like you. And this is such a hard question for women. I have a lot of women in my in my membership who are in their 50s and 60s who have never thought about this before. How do I want to look? I just want to be stylish. Cool, but what does that mean? Because style is so personal. Style is so personal. And your style might not be mine, mine's not yours. That's fine. If it makes you happy and you like the way you look, that's style. I don't let anybody in my organization use the word fashion. That is the F word to us. I absolutely not. Because fashion feels so heavy and difficult and frivolous and like something that I just don't have time for. That I'm intimidating. Yes, and it sounds uncomfortable. Let's be honest. But style, style is for everyone. Style is personal. Style, you can have style in your sweatshirts. You can have style everywhere you go. You have to get dressed. You might as well like the way you look.

Cheryl Fischer

Yeah, I love it. I love it. I know someone listening is getting curious. So tell us where can people find you?

Jennifer Mackey Mary

So the best place is probably my podcast, which is the Everyday Style School. And I like to say it's everything your mom never told you about getting dressed. All the things that mothers should have taught us, but they didn't know so they couldn't. We are changing that script. And then if you want to know more about everyday style and how we can work together, you can go to your youreverydaystyle.com, Y-O-U-R. And I actually teach a free class. It is called Style Made Simple. And you can go to freestyleclass.com and sign up. It's an hour, and I walk you through the five steps of style that again do not start with go to the mall. Uh we we walk from the beginning. We talk about how did

Where To Learn More With Jennifer

Jennifer Mackey Mary

we end up with all these clothes we don't like to wear? What are we gonna do next? How do we get started? All that good stuff. So powerful. It's never too late to learn. We have guilt that we don't know that we were born female, so we love to shop and know how to dress ourselves. No, it is a skill. It is absolutely a skill, and it's never, ever, ever too late to learn. And, you know, you're gonna have to get dressed every day for the rest of your life. Even if you don't know now, it's worth investing to learn how.

Cheryl Fischer

That's such a good point. And maybe that's your answer to the last thing I'm gonna ask you, but we'll see. I always say people are listening to this while they're doing the dishes, driving the car, whatever. So they're not gonna remember everything. They can always listen again, but they're not gonna remember everything. So, what is the one thing that you really want someone listening to take away from this?

Jennifer Mackey Mary

It's a thing that everybody knows, but it's worth reminding ourselves all the time that life is better when you like the way you look. And you can call me shallow and you can say it's frivolous, but remember the last time you felt cute where you put on an outfit and you were like, Oh, I really like this. You carried yourself differently. You carried yourself differently, you had a better day, you hit fewer red lights. I don't know what the connection is there, but it exists. I don't, I don't know. You smiled at strangers, you were more patient with people. And it has nothing to do with the expectation that you wear uncomfortable pants. Life is just better when you like the way you look. And one thing I find, and this really comes back to the idea of that life has gone casual, right? If we

The One Takeaway And A Challenge

Jennifer Mackey Mary

were all going to the office five days a week and had a reason to dress up, then we would be looking and feeling our best the majority of our lives. But now that we don't do that, we are not looking and feeling our best the majority of our lives. We are saving that for these occasions that are few and far between. I tell you what, I will go to somebody else's wedding looking like a hot mess. I don't care. You know what I mean? I mean, I I do care. I do. But if I had to choose the 99% of my life or that 1%, I'm choosing the 99%. Oh, that's powerful. I am choosing joy in my everyday life. And it's so dumb because it's like just find jeans that fit. You know what I mean? In all the problems in the world, and we know there are plenty, pants are pretty figure outable. There are problems I can't solve, but man, I can get I can find good pants.

Cheryl Fischer

Yeah.

Jennifer Mackey Mary

When you put clothes that fit, when you put on jeans that make you that make you remember how you used to feel, there's this moment where women say, and I have heard it so many times, why didn't I do this sooner? Life's just better when you like the way you look. I am not a shallow, frivolous person, I promise you. But I have seen women get promotions when they start dressing better. I have seen marriages restored, not because someone bought new jeans, but because they wanted to start dating their husband again. Wow. I have had women tell me, I yell at my kids less. Okay, didn't see that coming, but great. Wow. Life is just better. And it's an easy thing. It's low-hanging fruit. You have to get dressed every day. So why not choose to do it in a way that supports everything else? I did this, I did this challenge in one of my Facebook groups. And it was my challenge was get dressed before you leave your bedroom every morning for a week. I know it. And you know that song like, I'll do anything for love, but not that. Women are like, I'll do anything for better stuff, but not that. I gotta go have my coffee, I gotta check my email. Nope. You get you get you wake up, you get ready, you leave your bedroom. And at the end of the week, I said, How did it go? Were you more productive? And I remember someone saying to me, Well, I wasn't more productive, but I did find that I got my laundry done and I made my bed every day and uh and listed all these things. And I said, So the definition of productivity then? Is that is that what you're telling me? You did more things, yeah. You did more things in the same amount of time that you've always had? Yeah, that's actually called productivity.

Cheryl Fischer

Oh, that's interesting.

Jennifer Mackey Mary

It's just getting worse, but it's powerful. It's so powerful.

Cheryl Fischer

And that's a perfect way to wrap up. That's full circle to what we talked about at the beginning. And I I'm feeling inspired. Thank you. Thanks for joining us, Jennifer. This was great. My absolute pleasure. Thank you for having me. So it's all about how we feel. And it's just amazing to me to picture putting on something different having

Final Wrap Up And Reviews

Cheryl Fischer

that much of an effect. And I am a hundred percent, as you heard me say, on board with everything Jennifer's saying. And I've actually seen studies done, in fact, that studied if someone put on a lab coat, did they do differently on an exam than if they didn't have the lab coat on? Things like this. If someone had a uniform on, did that change something? And guess what? Yes is the answer. Yes. It changed the way they saw themselves. And I am inspired by this episode to go and figure out what it is that I want to highlight about my own body and how does that translate into style? And I hope that you are as well. Make sure that you connect with Jennifer, catch her podcast, the everyday style school, and hey, find me on social media, cherylpfischer tell me what you took away from this episode because I just think there are a million, a million amazing tips. Now, if you're listening on Apple, I would love it if you would tap the five stars and then leave a quick review. It doesn't have to be more than a couple sentences. You can say what's your favorite episode or what you've learned from the podcast. It makes such a difference because it tells Apple to share the podcast with more people. So thank you for doing that. And maybe I'll read your review on a future episode. And in the meantime, keep remembering midlife is your time to take just a little bit better care of yourself. On the inside and on the outside, like we've been talking about today, just a little bit better makes a big difference.