The Everyday Style School

40 Episodes
Subscribe

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.

✂️ Clip this podcast
Death, Taxes, & Great Style
#238
Today at 8:00 AM

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, and talking about how to navigate each one so great style can be as certain as death and taxes. 

All season long, I’ll be sharing stories of clients who struggled to dress through body changes, career changes, lifestyle shifts, and simply getting...


Fall 2026 Trends
#237
09/08/2026

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 season. We’re talking about the colors that are big, the biggest trend in denim, a couple of accessories you’ll see everywhere, and the Fall 2026 detail I’m obsessed with.

Plus, we dive into how to wear the trends. From how to...


Capsule Guides are Over--here's what's coming next!
07/20/2026

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. 


The Best Way to Build a "Ready for Anything" Wardrobe
#236
05/26/2026

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 this episode will help make it a reality.

In this episode, I talk about:

The six categories of clothes–from beach wear to black tieFive mistakes women make that make getting dressed harderCreating successful outfits that maximize your wardrobeH...


Everyday Style, Every Day
#235
05/12/2026

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 be one more thing on your to-do list, so I’m sharing what it takes to create an automatic habit of everyday style.

In this episode, I talk about:

The difference between having style every day, and having everyday style...


Can AI Make Style Easier? – Part 2
#234
04/28/2026

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 the same. How good is the advice? 

In this episode, I talk about:

Why my ChatGPT is better than your ChatGPTWhat AI models get right about dressing your body shape…and what they get wrongHow to ask bette...


Can AI Make Style Easier? – Part 1
#233
04/14/2026

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 apps availableWhy more information doesn’t always help improve your styleThree questions to ask yourself when considering AI style helpMy favorite thing about AI style apps- and why I don’t use them

If your social med...


10 Wearable Trends for Spring 2026
#232
03/24/2026

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 this episode, I talk about:

The colors and patterns that are having a moment this season.My personal favorite trends for Spring 2026How to know if the pieces in your closet are still current.

I hope this episode inspires...


4 Non-Style Habits That Actually Improve Your Style
#231
03/10/2026

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 when it seems like solutions to your style problems don't existWhy outfits and pieces that don't work can be the best teachersHow to improve your style while spreading kindness

Getting better style doesn't have to mean...


The B.A.S.I.C Formula for Simple (Not Boring) Style
#230
02/24/2026

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 effortThe simple style killer that might be living in your closetHow to keep basics from looking bland and boring

You can have the simplicity you want without sacrificing style, or becoming someone you're not, and this episode will help you get there.


Dressing Well is a Habit
#229
02/10/2026

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 dressed each day (and actually like the results).

I also share why dressing well has to become a daily habit, rather than something you only do when it really "matters", and how consistent practice is the key to...


Your Style Questions, Answered
#228
12/16/2025

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 learning the basics is just the starting point. How do you apply everything to your real life, your real body, and your real closet? I invited you to submit the questions that were holding you back, and that's what we're diving into today. 

From decoding color un...


The Personal Style Fundamentals You Should Know
#227
12/02/2025

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 breakthroughs don't come from following trends or mastering complicated styling formulas. They come from paying attention to what actually works for you. Today, we're unpacking 10 essential things every woman should know about herself if she wants getting dressed to feel easier, more fun, and authentically hers.

I hope this episode helps you...


How to Finally Understand Your Body Shape
#226
11/18/2025

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, I'm breaking down why traditional body shape labels like "apple," "pear," "hourglass," and "rectangle" aren't working for most of us. More importantly, I'm sharing a better way forward that doesn't require you to fit perfectly into a labeled box.

In this episode, you'll discover: 

The six major...


Understanding Proportion in Your Body and Your Outfits
#225
11/04/2025

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 outfits don't work. The missing piece? Understanding proportion. 

This episode is packed with the kind of knowledge that actually makes a difference in how you look and feel in your clothes. We're diving deep into what proportion really means, why most women get it wro...


Beyond Undertones: Color Theory Made Simple
#224
10/21/2025

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 together in your outfits. 

This isn't about handing you a color card and calling it a day—it's about giving you the knowledge to make confident color choices for life.

In this episode, you'll learn:

The three elements that every color hasThe bigg...


Do You Speak Style? Better Words, Better Wardrobe
#223
10/07/2025

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 things you can do to make shopping easier, faster, and so much more successful.

After 25 years of dressing women, I've seen how knowing the right words transforms the entire style experience. When you can name what you're looking for—whether it's a split v-neck blouse or palazzo pants—you stop wast...


Stop Making These 5 Fit Mistakes
#222
09/23/2025

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 the way sleeves hang, in how fabrics skim (or cling), in the numbers we get attached to, and in the “quick fixes” that actually make things worse. The good news? Once you know what to look for, these mistakes are easy to spot, and even easier to...


Style Fundamentals You Need to Master
#221
09/09/2025

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 are drowning in style advice while still struggling with the basics. We collect tips and tricks like they're going out of style, but we never build the foundation that actually makes everything else work. 

This season is my love letter to the fundamentals, and...


Style Rules are a Waste of Time
#220
08/28/2025

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 leave out, and why understanding the why behind what you wear makes style feel a whole lot less frustrating (and way more fun).

Full show notes and resources: https://youreverydaystyle.com/style-rules-waste-time


Spend Smarter, Look Better
#219
08/21/2025

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 actually live. 

If you’ve ever felt like your closet doesn’t reflect your real life—or like getting dressed is harder than it should be—this episode will help you spot what’s not working, and figure out if your issue is quantity, qual...


Not Just a Cute Outfit
#218
08/14/2025

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 between believing style doesn’t matter and believing it shouldn’t, where that mindset comes from, and how to reframe it so you can start using style as the powerful tool it really is—not just for looking good, but for living fully.

Full show notes a...


Style from the Inside Out
#217
08/07/2025

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 stylish woman from the inside out. This one’s short, powerful, and packed with take-action tips.

Full show notes and resources: https://youreverydaystyle.com/inside-out


Stop Wasting Money on Single Use Outfits
#216
07/31/2025

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 panic instead of preference leads to ill-fitting, off-brand purchases, and how these one-off items create closet confusion. 

I share practical strategies for planning ahead, preparing your closet for impromptu special occasions, and embracing that caring about how you look isn't frivolous - it's about living more fully in th...


Is Your Closet a Boutique or a Museum?
#215
07/24/2025

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 why your closet shouldn't be a museum to who you used to be or storage for who you might become. You’ll also get practical tips for upgrading your space.

Full show notes and resources: https://youreverydaystyle.com/closet-boutique-museum


The Only Opinion That Matters
#214
07/17/2025

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 you love leads to the expensive "should" trap, and why buying clothes you think you should have makes you feel like a style imposter. 

I share practical exercises to help you identify what you actually love in your closet and start trusting your own ta...


Your Wardrobe’s Bottom Line
#213
07/10/2025

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 bottoms. Plus, I explain why we overbuy tops and neglect our bottoms, and the wardrobe problems that strategy creates. 

Finally, I give you a step-by-step process to diagnose which problem you need to solve before you spend another dollar on clothes.

Full s...


Style From the Ground Up
#212
07/03/2025

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 not only waste your money, but can actually make you think you're bad at style. 

I'm also giving you practical steps for finding better shoes for the way you really live, and using them to boost your style. 

Full show notes...


Your Everyday Matters
#211
06/26/2025

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 Simple Challenge about why this mindset shift is harder than it seems, and give you a practical challenge to uplevel your daily outfits without making them dressier. 

If you've ever thought, "I'm not going anywhere special today, so who cares what I wear" this episode is for...


10 Wearable Trends for Summer 2025
#210
06/06/2025

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 for you.

Need more help getting your wardrobe looking current? Many of these styles are featured in our Summer 2025 Capsule Wardrobe Guide, available June 5th. The Guide shows you how to combine 39 pieces (mostly basics, with a few trends peppered in) to create ov...


The 30 Minute Closet Edit You Can Do This Week
#209
05/22/2025

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 editing process that not only makes seasonal transitions smoother but actually refines your wardrobe over time. 

This isn't about trying on everything you own or making perfect decisions - it's about quick, strategic choices that make getting dressed easier now and in the future.

...


The Habit Keeping You From the Wardrobe You Want
#208
05/01/2025

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 shopping isn't just those planned shopping trips with girlfriends; it's any time you buy clothes you weren't expecting to, from impulsive Target t-shirt purchases to vacation souvenirs that never make it out of the closet once you're home. 

In this episode, I'm breaking down why this ha...


Stop Looking Dated, Part 2
#207
04/17/2025

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, remember my golden rule: wear what you love! This isn't about forcing you to abandon favorite pieces, but rather giving you the knowledge to make informed style decisions.

Here's what you'll learn in this episode:

Why items you still love...


Stop Looking Dated, Part 1
#206
04/03/2025

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 clothes. This first part focuses on understanding what "dated" really means, why looking current matters, and how to recognize dated styling. Let's get started on freshening up your look!

Here's what you'll learn in this episode:

The difference between trendy, current, classic, and...


Style Lessons I Learned From Baking Sourdough Bread
#205
03/20/2025

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 through my complete bread-making journey, from the overwhelm of too much information to the joy of finding my own approach.

Through my story of exploding dough and burnt bottoms, I extract five powerful lessons that can apply perfectly to your style journey.

Here's some o...


10 Wearable Trends for Spring 2025
#204
03/06/2025

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 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 for you.


Reset Your Home with Ingrid Jansen
#203
02/20/2025

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 30+ years of experience, with insights from her new book "Reset Your Home," Ingrid shares a fresh judgment-free perspective on creating lasting change.

Whether you're drowning in paperwork, struggling with an overstuffed closet, or just can't seem to maintain order in your home, this conversation will help you to create t...


Bonus! Ready to Look Better In Your Clothes?
02/11/2025

You know that feeling when you know something about your outfit is "off", but you don't know what it is...or how to fix it?

We've all been there, and it can be super frustrating, so I've put together a totally free  live class to help you troubleshoot your outfits, so you can easily love the way you look.

Join me for "5 Ways to Look Better in Your Clothes" coming up on Tuesday, Feb 18 at 7:00 central. In this zoom class you'll learn:

The #1 style killer that 80% of women are guilty ofWhy some ou...


Do as I Say, Not as I Do: The Style Advice I Give, but Don't Follow
#202
02/06/2025

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 I apply these principles in my own life. More importantly, I want to share why sometimes breaking the "rules" makes sense, even when the advice itself is solid.

Here's what I shared in this episode:

Why I don't strictly follow a...


10 Ways to Boost Your Style in Under 10 Minutes
#201
01/23/2025

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 your style game in less than 10 minutes?

In this episode, I'm sharing 10 super simple style hacks that will help you look more put together every single day – and most of them can be done in just 2 minutes or less! Whether yo...