Death, Taxes, & Great Style

The Everyday Style School

The episode explores how to navigate inevitable life changes—such as body shifts, career transitions, and lifestyle evolutions—through the l

Key takeaways

• A true wardrobe consists only of the clothes you actually wear and can wear, not everything you own.
• Clinging to old clothing often stems from guilt over wasted money or a desire to hold onto a previous identity.

Main topics

• Navigating life transitions
• Wardrobe mindset and psychology

Notable quotes

What's in your mind matters way more than what's in your closet.

Conclusion

By reframing clothing as functional tools and letting go of the past,

Transcript preview

Speaker 1 (0:00) In 1789, United States founding father Ben Franklin wrote in a letter, quote, In this world, nothing can be said to be certain except death and taxes, end quote. Now, he wasn't the first person to share this idea, and he was talking about the durability of the United States Constitution and not his wardrobe. But there is an important lesson to be learned here, and that is change is inevitable. And as women, don't we know it? Body changes, trend changes, lifestyle changes. These upheavals can wreak havoc on your closet, your style, and your psyche. So this season, we're talking about how to navigate all kinds of life change so that three things can be certain, death, taxes, and great style. Let's get started. Speaker 1 (0:57) Welcome to the Everyday Style School, the show that teaches you everything your mom never did about getting dressed. I'm your host, Jennifer Mackey-Mary. After 25 years of dressing women with real bodies, real budgets, and real lives, I know great style isn't about following one-size-fits-all advice. It's about learning what works for you. Speaker 1 (1:18) Hello, gorgeous. I hope you enjoyed the fall trends episode that came out just a couple weeks ago. Those are always fun to put together because it's really the first look at what is new and different for the season. And while this is sort of our first official episode of the fall semester, the trend episode fits in really well with this season's theme, which is, of course, stylishly navigating all of life's changes. Real quick. I want to hop into the Wayback Machine and talk about where the idea for this season came from. Early this year, I think it was like January or February, I don't know, it was still freezing outside, my husband and I found ourselves in our closet at the same time getting dressed, which never ever happens. We both work from home, so we're not on the same morning schedule, and that's a very good thing because our closet is this long, narrow, galley-style thing. It is not roomy enough for two people to be in there comfortably, especially when one of them has severe crippling claustrophobia. That is me, by the way. So there we were getting dressed, me trying to play it cool and not have a panic attack because the walls were closing in on me. And he pulled out this sweater that gave me a, I don't know how to describe it. It was like a Matrix style movie flashback because I bought that sweater for him. the year we got married, which was 2004. For the math challenged among us, that is 22 years ago, 22 years. And he said, oh, I forgot about this. He put it on, still fit, still look great. And as he stood there in his chinos and cashmere crew neck, I had a memory of him wearing the same outfit on a date 22 years ago, chinos and that cashmere crew neck. It was a total trip. It was like I traveled back in time. And is he the exact same guy I married? No, absolutely not. We have lived a lot of life together. We have had kids. We've moved across the country. We've lost family members, sent a kid to college. But as I looked at him in that same sweater he wore 22 years ago, I felt like I have lived five lifetimes since then. When we met, I was a corporate girly, getting dressed up each day, going out a few nights a week. And after we got married, later I became a stay-at-home mom and my wardrobe and my body were very different. After another baby and more body changes, I started a business and I had to start getting properly dressed again. I needed a wardrobe of things to see clients in and things to wear on stage for speaking engagements. And then we moved. And my business went completely online and I found myself not needing the same kind of wardrobe. I needed to feel put together while not going anywhere or seeing anyone. Perimenopause hit and my shape shifted again. And this doesn't even include all of the trips up and down the scale I have taken in 22 years. Since we met, my body has changed. My style has changed. My lifestyle has changed. The trends have changed. All of it has changed multiple times. Not a single sweater has survived. And it made me think about all of the changes we navigate as women and how difficult dressing through those changes can be. But I also thought about how your wardrobe can make a season of change easier or more difficult. And that was when I knew that this had to be something we dug into for an entire semester. Speaker 1 (5:03) I understand that it is a total oversimplification to say that women have all these changes and men just say the same and don't deal with any of this stuff. And that is not at all what I'm saying. But I do feel comfortable saying that we probably have more. And while the chinos my husband wears today are different than he wore back then, I have yet to see the man choose an outfit because of... hot flashes and what he can take off and still look appropriate, right? I haven't seen him choose pants based on what's comfortable on his C-section belly. I haven't seen him wondering if ballet flats were passe and then wondering if they were back in and then wondering if they were passe. I mean, it's been 22 years. It's happened a lot, right? I know that he saw my postpartum wardrobe meltdowns when I literally had nothing to wear. And I know he's seen my struggles when my clothes were too big to look good or too small to feel good. To be honest, I can't recall a single meltdown he has had about jeans. And maybe he just holds it in. It's totally possible. And maybe I just live my struggles out loud. But the point is, women change a lot. Our needs change a lot. Our wardrobes change a lot. And every change can