The Everyday Style School
by Jennifer Mackey Mary
Welcome to the show that teaches you everything your mom never did about getting dressed! The Everyday Style School inspires you to love the way you look everyday, and gives you the tools to make it easy. From understanding your body shape, to getting rid of clothes that no longer serve you, we give real style advice to women with real lives, real bodies, and real budgets.
Episodes
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Navigating Weight Changes Stylishly Pt. 1
Have you been putting your style on hold, waiting for your weight to change? For a lot of women, the belief that they'll have better style when they reach a certain size keeps them from enjoying the wardrobe they have today. In this episode, we're talking about the beliefs that hold us back from...
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When Your Wardrobe Doesn’t Feel Like You
Your personal style is supposed to be an expression of who you are, but what happens when your wardrobe is still reflecting who you used to be? Or when you've never really figured out what your personal style is in the first place? A lot of women focus on learning and following all the rules,...
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Five Lessons from Overhauling My Wardrobe
Over the last two years, I’ve rebuilt almost my entire wardrobe, from underwear to outerwear. I’ve helped women navigate wardrobe changes for decades, but doing it myself gave me a whole new appreciation for the process. Along the way, I’ve learned a few things. I’ve been helping women create...
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Death, Taxes, & Great Style
As women, we know life is all about changes: from our bodies, to the trends, to our lifestyles, these upheavals can wreak havoc on our closets, our wallets, and our psyches. Life is uncertain, but your style doesn’t have to be. This semester, we’re digging into all the changes life throws at us,...
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Fall 2026 Trends
The Everyday Style School is back from summer vacation with a look at what all the cool girls (that’s you!) will be wearing this season. As always, there are tons of runway trends being talked about, but in this episode I’m covering a few of the Fall 2026 Trends you’ll actually see in stores this...
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Capsule Guides are Over--here's what's coming next!
After more than 40 Capsule Wardrobe Guides, we're saying goodbye. Listen to find out why...and what's next! Want to join the Style Circle before we close (and lock in the lowest rate ever)? Sign up before July 28th! youreverydaystyle.com/the-style-circle.
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The Best Way to Build a "Ready for Anything" Wardrobe
Feel like you never have the right thing to wear? You’re not alone. Most women have Goldilocks closets–full of clothes that are too dressy, or too casual, when all they want is a wardrobe that feels just right. Building a perfect “ready for anything” wardrobe doesn’t have to be a fairytale, and...
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Everyday Style, Every Day
Discover how to make style easy…for life. Get my FREE style class: Style Made Simple freestyleclass.com You’ve got better things to do than spend 20 minutes picking the perfect errand-running outfit, but that doesn’t mean you can’t be stylish on days you’re not going anywhere special. Style can’t...
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Can AI Make Style Easier? – Part 2
Discover how to really make style easy…for life. Get my FREE style class: Style Made Simple freestyleclass.com In our last episode, we explored whether AI style apps can really make style easier, and this week, I'm taking a look at AI models like ChatGPT, Gemini, and Claude, to see if they can do...
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Can AI Make Style Easier? – Part 1
Get my FREE style class: Style Made Simple freestyleclass.com These days, AI is everywhere – including our closets. But can it really make style easier, or better? That’s what I’m on a mission to find out. In this episode, I talk about: The pros and cons of some of the most popular AI styling…
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10 Wearable Trends for Spring 2026
Get my FREE style class: Style Made Simple freestyleclass.com Spring is one of style's best seasons, and a great time to update your wardrobe with a few trending pieces that will keep you looking fresh and current. Today, I'm sharing 10 trends that real women with real lives can easily wear. In...
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4 Non-Style Habits That Actually Improve Your Style
Get my FREE style class: Style Made Simple freestyleclass.com Improve your style by working smarter, not harder! There are so many habits you already do on a daily basis that can be applied to your wardrobe, and I'm sharing four of them with you today. In this episode, I talk about: What to do…
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The B.A.S.I.C Formula for Simple (Not Boring) Style
Get my FREE style class: Style Made Simple www.freestyleclass.com If you love simple style but are tired of looking underwhelming instead of understated, this episode is for you. In this episode, I talk about: Five ways to look more put together without extra effort The simple style killer that...
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Dressing Well is a Habit
Get my FREE style class: Style Made Simple www.freestyleclass.com We're back, and kicking off the Spring semester, which is all about making style easier in your everyday life! In this episode, I talk about why you can have all the technical style knowledge in the world, but still struggle to get...
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Your Style Questions, Answered
We've reached the end of our fall semester, and I couldn't think of a better way to wrap things up than by answering YOUR questions. If you've been following along this season, you've learned about fit, color, proportion, body shape, and the fundamentals that make getting dressed easier. But...
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The Personal Style Fundamentals You Should Know
How well do you really know your personal style? I'm talking beyond the surface-level stuff—like whether you gravitate toward black or prefer bright colors. In this episode, we're diving deeper into the often-overlooked foundation of great style: truly understanding yourself. The biggest style...
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How to Finally Understand Your Body Shape
If you've ever taken a body shape quiz only to feel more confused than when you started, you're not alone. Despite all the resources out there—quizzes, blog posts, entire businesses built around body types—understanding and dressing your shape remains the #1 challenge I hear from women. Today…
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Understanding Proportion in Your Body and Your Outfits
Let's talk about the topic that makes me geek out more than anything else in the style world: proportion. I know, I know—it doesn't sound exciting. But here's what I've learned after dressing thousands of women: you can have all the right pieces, follow all the rules, and still feel like your...
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Beyond Undertones: Color Theory Made Simple
Have you ever wondered why some color combinations look effortlessly chic while others feel like a fashion miss? It all comes down to understanding how color actually works. In this episode, I'm breaking down the three fundamental elements that affect both how colors look on you and how they work...
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Do You Speak Style? Better Words, Better Wardrobe
Have you ever ordered something online that looked perfect in the description, only to be completely disappointed when it arrived? Or struggled to explain to a sales associate exactly what you're looking for? Today, I'm sharing why building your style vocabulary is one of the most practical…
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Stop Making These 5 Fit Mistakes
This season, we're focusing on the fundamentals, and there's nothing more fundamental to your style than fit. In this episode, I’m breaking down the most common pitfalls I’ve seen over the years that make great wardrobes look just okay, instead of amazing. Fit mistakes are sneaky. They show up in...
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Style Fundamentals You Need to Master
If you've been listening to style advice for years but still find yourself staring at a closet full of clothes you never wear, there's a good chance you've been focusing on the wrong things. I'm changing up the Everyday Style School this season because I've had an important realization—most of us...
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Style Rules are a Waste of Time
If you’ve ever followed all the style “rules” and still felt stuck, this one’s for you. In this episode, I’m sharing one of the biggest reasons traditional style advice doesn’t actually help you become more stylish—and what to do instead. We’ll look at how rules oversimplify things, what they…
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Spend Smarter, Look Better
In this episode of Summer Shorts, I’m sharing one of the most practical—and eye-opening—style lessons I’ve learned: Spend your money where you spend your time. I’ll tell you about the client who helped me see how often there’s a disconnect between the clothes we invest in and the lives we…
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Not Just a Cute Outfit
In this week’s episode of Summer Shorts, we’re unpacking a hidden belief that might be keeping you from loving your wardrobe—or even building one that works. If you’ve ever felt like caring about clothes is silly, shallow, or self-indulgent, this one’s for you. We’re exploring the difference...
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Style from the Inside Out
In this episode of Summer Shorts, we’re flipping the script on where true style starts. Spoiler alert: it’s not your jeans or your blazer—it’s what you wear when no one is watching. From your underwear drawer to your self-worth, we’re connecting the dots between unseen style and becoming a…
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Stop Wasting Money on Single Use Outfits
In this episode of Summer Shorts, I tackle the expensive mistake of last-minute clothes shopping and why those panic purchases never become wardrobe favorites. I explain the real reasons we find ourselves sweating in fitting rooms at 9 PM (spoiler: it's not just poor planning), why shopping from...
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Is Your Closet a Boutique or a Museum?
In this episode of Summer Shorts, I share my favorite piece of style wisdom about transforming your closet into the boutique you shop from each morning. I break down the two parts of creating this boutique experience - what's actually in your closet and how the space makes you feel - and explain...
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The Only Opinion That Matters
In this episode of Summer Shorts, I tackle something that sounds simple but keeps so many women stuck: giving yourself permission to like what you like. I explain why asking "what do WE think?" about your outfits is the wrong question, how focusing on getting style "right" instead of wearing what...
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Your Wardrobe’s Bottom Line
In this episode of Summer Shorts, we’re getting to the root of your wardrobe problems by revealing where they actually live: in your pants. I’ll share the story of a client who tried unsuccessfully to solve the wrong wardrobe problem, and break down the three specific problems hiding in your...
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Style From the Ground Up
In this episode of Summer Shorts, I’m diving into my most repeated, but misunderstood, piece of advice! I share the story of a client whose wardrobe didn’t come together until she solved the right problem, explain why women hear when I say “shoes define your style”, and reveal how the wrong shoes...
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Your Everyday Matters
In the first episode of our Summer Shorts series, I’m breaking down a fundamental style concept that changes everything: the difference between dressing well and dressing up. I share why this distinction is the foundation of everything we do at Everyday Style, reveal insights from the Style Made...
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10 Wearable Trends for Summer 2025
In this episode, I’m sharing 10 trends for Summer 2025 that you can work into your real-life wardrobe to look current without feeling like you’re trying too hard or that you raided your teenage daughter’s closet. Listen and learn what’s trending for the season and tips for making the trends work...
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The 30 Minute Closet Edit You Can Do This Week
Do you dread the seasonal wardrobe changeover? Let's be honest - pulling out bins, packing away clothes, and managing a closet that's bursting at the seams isn't anyone's idea of fun. But what if it didn't need to be so painful? In today's episode, I'm sharing my game-changing 30-minute closet...
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The Habit Keeping You From the Wardrobe You Want
Let's talk about what I believe is one of the most destructive style habits you can have - recreational shopping. After over 25 years as a stylist, I've seen how this habit wastes money, confuses style, and leaves women with "nothing to wear" despite having closets full of clothes. Recreational...
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Stop Looking Dated, Part 2
Are you ready to find out if what you're wearing is out of style? This is part 2 of our "Stop Looking Dated" series, and while part 1 focused on HOW we wear our clothes, today I'm sharing 10 specific pieces that have had their moment but are now killing your quest to look current. As always,...
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Stop Looking Dated, Part 1
Are you adding on-trend pieces to your wardrobe but still feel like something's off? In today's episode, I'm tackling a topic that might ruffle some feathers—how to stop looking dated! Over the next two episodes, I'll share how to turn the style ship around without necessarily buying a ton of new...
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Style Lessons I Learned From Baking Sourdough Bread
In this episode, I take you along on my sourdough bread baking journey and reveal the surprising style lessons I discovered along the way. What began as a TikTok-influenced adventure quickly turned into a personal exploration of perfectionism, fear of failure, and finding my own path. I walk you...
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10 Wearable Trends for Spring 2025
Winter is over, and one of Style’s best seasons is here! Spring is when we get our first look at what’s big for the warm months, and this season, there are so many great looks out there. In this episode, I’m sharing 10 trends (plus a bonus!) for Spring 2025 that you can work into your real-life...
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Reset Your Home with Ingrid Jansen
Ready to transform your relationship with clutter? In this enlightening episode, I sit down with Ingrid Jansen from The Declutter Hub to explore why traditional organizing methods often fail us and how understanding our emotional connection to stuff can lead to lasting change. Drawing from her…
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Do as I Say, Not as I Do: The Style Advice I Give, but Don't Follow
Today, I'm pulling back the curtain to share something I've been thinking about a lot lately - which pieces of my own style advice I actually follow, and which ones I don't. As someone who gives a lot of guidance about building a better wardrobe, I think it's important to be transparent about how…
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10 Ways to Boost Your Style in Under 10 Minutes
Is there ever a morning when you feel like you just don't have time to look put together? As a wardrobe stylist who's worked with thousands of women, I know that mornings can be hectic, and style often takes a backseat to just getting out the door. But what if I told you that you could elevate…
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Rethinking Fashion Waste with Amelia Trumble
Have you ever finished a closet cleanout and found yourself staring at a pile of clothes, completely stumped about what to do with them? In this episode, I'm tackling the often-overlooked but critically important question of what happens to our clothes after we're done with them. From well-loved...
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The 2024 Style Survey Results are In!
Do you ever wonder if you're the only one struggling to get dressed, or if you spend way more (or less) on clothes than other people? Well, you're not alone! In this special episode, I'm breaking down the fascinating results of our 2024 Style Survey, where thousands of women shared their most...
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10 Wearable Trends for Winter 2024
In this episode, I’m sharing 10 trends for the season that you can use to look current and boost your spirits while the days are cold and short. Listen and learn what’s trending for the season and tips for making the trends work for you. Need more help getting your wardrobe looking current? Many…
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Stop Wasting Money and Build a Better Wardrobe
Are you tired of buying clothes that don't solve your style struggles? In today's episode, I'm revealing how creating a strategic shopping list will transform how you approach your wardrobe and save you money. By tuning in, you'll discover: A revolutionary approach to shopping that can help you...
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Playing Big with Tara Mohr
Have you ever felt like you were holding yourself back? In this powerful conversation, I sit down with Tara Mohr, the bestselling author of "Playing Big: Practical Wisdom for Women Who Want to Speak Up, Create, and Lead." Together, we dive deep into why so many of us (yes, me included!) find...
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Online vs. In-Store Shopping: What’s the Best Style Strategy?
Do you have a favorite way to buy clothes? Do you prefer to shop online, with a glass of wine and no bra? Or do you like to put on pants and actually go to the store? When it comes to building a fabulous, functional wardrobe, is there a "best way to shop? That’s what this episode is all about! In…
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The Fall Transition Pieces I'm Wearing On Repeat
Whether you're dealing with cool mornings that turn into warm afternoons or you're stuck in a Summer rut while waiting for Fall, this time of year can be a real challenge for getting dressed. To help you make the most of fashion's best season, I've got a few simple strategies that will help you...
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My Style Struggles
One of my pet peeves is experts who appear to know it all and never struggle. And in our Instagram-filtered world, this is only getting worse. But guess what? Everyone has their off days! As a wardrobe stylist with over 20 years of experience, I believe in the power of sharing our challenges to...
Topics in this show
About this show
Welcome to the show that teaches you everything your mom never did about getting dressed! The Everyday Style School inspires you to love the way you look everyday, and gives you the tools to make it easy. From understanding your body shape, to getting rid of clothes that no longer serve you, we give real style advice to women with real lives, real bodies, and real budgets.
Hosted by
Jennifer Mackey Mary