Five Lessons from Overhauling My Wardrobe

The Everyday Style School

Jennifer Mackey-Mary shares five lessons from rebuilding her own wardrobe after a significant size change over the last two years. She contr

Key takeaways

• Rebuilding a wardrobe is expensive and mentally exhausting because it requires replacing unfun basics like underwear, jeans, and shells, not just statement pieces.
• Jennifer plans basics quarterly and uses her calendar to identify upcoming events like holidays, her anniversary, a November concert, and networking events.
• She advises buying less rather than buying cheaper during transitions, using a client who needed only eight office outfits instead of twenty as an example.
• Buying ahead is discouraged; she donated tagged maternity clothes bought at Old Navy after following clearance advice from The Bump.
• She recommends solving one wardrobe category at a time, such as beyond-basic tops, to avoid duplicates and overwhelm.

Main topics

• Wardrobe overhaul after a size change
• Planning a functional wardrobe by season and calendar
• Buying less and avoiding overbuying during transitions

Notable quotes

overhauling your entire wardrobe is not as much fun as you might have envisioned

Conclusion

The episode is practical and self-aware, offering a grounded framework for

Transcript preview

Speaker 1 (0:00) Have you ever looked at your closet and just wanted to start over, burn it all to the ground and completely start from scratch? Sometimes the idea of building a whole new wardrobe sounds really good. You could get rid of all of those shopping mistakes and the clothes that you can't part with even though you haven't touched them in ages. You have visions of only putting the right things into your closet, maybe even having a minimalist, chic wardrobe like all the Parisian style experts claim to have. Well, friends, over the last couple of years, that's basically what I've done. I've rebuilt my entire wardrobe from underwear to outerwear. And today I'm sharing what that really looks like, the good, the bad, the costly, and what I've learned in the process. Let's get started. Speaker 1 (0:58) 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 (1:20) Hello, gorgeous. This is an episode I have wanted to do for a long time. Literally every time I do another round of closet edits and add more of my favorites to the discard pile, I've thought, I can't wait to talk about this. And it's kind of funny because all of the lessons I'm sharing today are things I've known, right? I've been helping women rebuild their closets for over two decades. So this is nothing new. But there's a difference between doing something for someone else and actually doing the thing for yourself. But truly, nothing I'm telling you today is any different than what I would have told a client going through the same thing. And there have been some times over the last couple of years where I've had to stop and remind myself of that. I've had to say, okay, Jen, what would you tell someone if you were on the other side of this? And that is a theme that will come up later in the season and a bunch of episodes. But it's a really good reminder that often we are too close to the problem and our feelings and our overwhelm get in the way of what we know, right? That knowledge that would actually make the problem a whole lot easier to handle. We just have to step back and look at the situation and ask ourselves, what do we know about how to fix it? And then take action. That is the reason we teach the five fundamental skills of style inside of our membership. Yeah, finding pants is really hard until you learn what to look for when you buy pants. Building a fabulous functional wardrobe is hard until you learn how. When you have the skills to solve the problem, everything is figureoutable. When you don't though, everything feels hard and unsolvable. So today we're going to talk about five lessons you can learn from my ongoing quest to rebuild my wardrobe. But first, I just want to acknowledge why I had to rebuild my wardrobe. As longtime listeners probably know, my weight has been something I have struggled with my entire life. Over the last couple of years, my size has changed a lot, which has meant my wardrobe has changed a lot too. I'm not going to get into the specifics of my weight because that's not really what this episode is about. It's about the experience of rebuilding my closet and what you can learn from it. I just think it would be kind of strange to talk about this major upheaval and not mention the reason for it. So there you have it. I weigh less than I used to and I had to get new clothes a few times. Let's move on. The first lesson from me rebuilding my closet that everybody needs to hear is that overhauling your entire wardrobe is not as much fun as you might have envisioned. I think that when we imagine a total wardrobe transformation, it's like a glow up in a movie, like from Bridget Jones's diary. There's the before and everything is bad and everything is terrible and you want it to change. And then there's like this three to five minute montage set to a really catchy song where the transformation happens. Maybe it's. shopping, carrying pretty boutique bags, or trying things on in a fitting room where, of course, everything looks fantastic on you. And then there's the end with a well-organized, well-lit closet full of beautiful things. And scene. Speaker 1 (4:55) Yeah, the reality looks a little different. First of all, have you ever done the math on what it would cost to completely start over? Yeah, me neither. Because at this point, I don't want to know. At this point, I'm like, it is none of my business. I can't even budget for it because when you need underwear that don't fall down when you walk, you're not going to say. Oh, well, maybe I'll put that in next season's budget. No, you just have to go buy the underwear. Now, there are ways to spend smarter when you are rebuilding, and we are going to talk about a couple of them later in the episode and all throughout the season. But the point is, rebuilding your wardrobe isn't just upgrading a few pieces and voila, everything is new. No, it's about upgrading the unfun stuff too. Speaker 1 (5:45) The other reason starting over is not as much fun as you might imagine is that it requires a lot of mental energy. This might come as a huge surprise to you, but I don't actually like to think about clothes that much, especially in my personal life. I think about clothes all day for work and that is great, but something I value a lot and something I teach is intentionally building a wardrobe that you don't have to think about every day. It is exhausting. And to those of you who haven't built a wardrobe that makes it easy to get dressed, I just have to say, I don't know how you do it. Honestly, I don't know why you do it. It's not fun. Wardrobe fun to me is getting dressed in three minutes or less and liking my outfit. Like that is a really good time in my world. But this thing about what am I going to wear? Do I have all the pieces? Do they look right together now? Are the jeans too sloppy to wear with that sweater? I just can't. I am tired. If nothing else, the last two years have taught me the importance of creating a wardrobe and a closet that requires almost zero mental energy. Speaker 1 (7:00) Sometimes challenges change your thinking and that's great. But sometimes they just cement what you already believe. And this is a really good example of the second one for me. Hands down, having a wardrobe you don't have to think about is better than one that requires mental energy. I completely understand Zuckerberg and his t-shirts a whole lot better now. I actually think it's a great plan. So crazy story for you. Years ago, I was in a moms in business group. We probably called them mompreneurs. Oh, hate that term. But anyway, I was in this group with a woman who went to dinner with her husband and her five kids. On their way home, they saw smoke in their neighborhood and she jokingly said to her husband, do you think that's our house? I'm sure you can imagine how this story turns out. Yes, it was their house. Everything they had burned to the ground in the couple of hours they went to dinner and ran a couple of errands. Like that is absolutely horrific. A few weeks later, after they were settled into temporary housing, she called me and she said, I have no clothes and I don't know what to do. Now, I have worked with a lot of women who have told me they have no clothes, and I am always reminded of the one woman I know who could actually say that. But in a way, building a wardrobe from that perspective, from literally nothing, was easier. She wasn't dealing with all of the, I mean, it's fine, I could wear it stuff that most of us struggle with. She wasn't thinking, do I have something that will go with this skirt? No, she didn't. It was truly a clean slate closet-wise. We worked together quarterly for about a year and it was just adding rather than making choices about what to do with the things that were okay but not great, which is where most of us struggle. It isn't the adding part that's hard. It's the culling. But most wardrobe transformations aren't this single instant watershed moment and then a total rebuild. They are slow like mine and often it can feel like you are never done and that also takes a lot of mental energy. And that brings me to lesson number two. You need to plan ahead. Like I said a few minutes ago, I just find it so draining to struggle to get dressed. I have better things to do than try on outfit after outfit, hoping something in my closet works, hoping I have the right pieces. No, thank you. I opted out of that nonsense a long, long time ago. But the only way to avoid that particular stress is to know what you're getting dressed for and make sure you have something for it. I do this in a couple of ways. First, I plan my basics quarterly. The nice thing is my business runs on quarters with our style guides. So I have a really clear reminder that, hey, it's time to think about fall, for example, like what are the key pieces for the season? Obviously it's fall. I can't be