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.

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. 

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’ 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. 

Yeah, um, 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. 

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. 

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 call 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 without good jeans. So that will be on my seasonal planning list. It means I try on the jeans I have, hope something fits, but if nothing does, I make a plan to replace it. Same with sweaters, sweatshirts, light jackets, whatever. 

That sets the tone for a functional wardrobe. And a functional wardrobe is one that gets you dressed easily and appropriately for the majority of your life without crying or emergency shopping. 

The other way I plan ahead is with my calendar. What do I know I have coming up that I need to get dressed for? If I look at the next three months, I know I have the holidays, I know I have my anniversary, and my family got me tickets to a concert in November that I’m stupidly excited about. I also have some networking type events that I need to dress up for.

These are things outside of my regular routine that I want to look good and feel special for. This is part of having a fabulous wardrobe, which means going beyond just the basics you need and putting some personality into it. 

The reality is these kinds of pieces, the fabulous kind of pieces, these are the things women think they’re saving style for, but when it comes time to wear those things, they don’t actually have anything to wear because they didn’t put it into their closets in the first place. A fun outfit for a concert that makes you feel the way you want isn’t going to magically materialize just because you bought tickets. You have to put the right pieces in there. So at the beginning of the season, I think, what do I know about? And I start planning ahead.

When something comes up that I didn’t plan on at the beginning of the quarter, I don’t wait until the last minute to figure out what I’m going to wear. Because in the best of times, you might not have the right thing for something that isn’t a part of your regular routine. But when your wardrobe is in a period of upheaval, you need to behave as if you definitely don’t. Because the truth is you probably don’t. 

The energy that you spend planning ahead at the start of the season is nothing compared to the energy you spend struggling all season long if you don’t. This is really important when your wardrobe isn’t in transition, but it is critical when it is. 

The third thing I’ve learned from rebuilding my entire wardrobe is that you don’t need as much as you think you do. I realize that’s a wild thing for a wardrobe stylist to say, but it’s true. 

This is a lesson I learned when I first started my in-person styling business about, what, 14 years ago now? And I was working mainly with women who were in the postpartum, are we done having kids yet phase. You know the one, right? Nothing fits you. Anything that does fit you is out of style, but you’re not sure where you’re going to end up. So you don’t really want to invest in much, but you still have to get dressed. This is seriously one of the hardest times for women wardrobe wise and otherwise. And this one can last for years. 

One thing I’ve heard over the years from my clients who were going through this kind of change, especially my postpartum clients and my women who have had weight loss surgery, was that it is so expensive to keep buying clothes that you don’t wear for long. And I am not gonna argue with them at all, it absolutely is. But their solution was always to buy cheaper stuff. It never occurred to them to just buy less stuff. And I am not saying that if you just had weight loss surgery or you just had a baby, you should go invest $240 jeans that you will only wear for, I don’t know, three, six months. 

There’s a practical reality here as well. But you also don’t need six pairs of $40 jeans. It’s the same money spent and you really don’t need six pairs of jeans. One of the best ways to save money during periods of transition is simply not buying more than you need, rather than just buying more cheap stuff.

I worked with a client once who was going back to work and we did not do a closet edit because she didn’t have any office appropriate clothes to build on. We were truly starting from scratch and she wanted to get a full work wardrobe. Trousers, blouses, dresses, pants, blazers, the works. Like I said, she had nothing and she wanted to just knock it out. 

She booked both of my shopping spots on one day because she just wanted to be done and God love her. I love a woman on a mission. 

But during the second three-hour shopping block, she made a comment about how she was really grateful that she only had to sit in DC Beltway traffic, if you know, you know, twice a week.

And I was like, well, wait, where will you be the other three days? Thinking that maybe she was going to be on client sites and need different kinds of clothes, whatever. Nope. She only had to go into an office two days a week. The other three, she worked from home. 

That is eight days of office outfits versus 20 days of office outfits. She needed less than half of what she originally thought. And this wasn’t like budget was of no concern for her. She had that sort of, well, it hurts, but I have to do it vibe when she was buying the clothes. But the thing is, she actually didn’t have to do it.

Overbuying during periods of transition costs a lot of money on the front end, but it causes secondary problems as well. 

Think about it. If you bought two pairs of jeans and the next year when you pulled them out, they didn’t fit, you would think, oh, okay, I need to replace two pairs of jeans. But if you bought the six pairs of jeans and none of them fit, you think, oh man, that’s a lot of clothes to get rid of. I spent a lot of money on those. I should probably hold onto them in case I need them again someday. 

So you have to add clothes to your closet that you can wear now because you need to get dressed now, but you’re piling them on top of clothes you can’t wear anymore, but feel too guilty to get rid of. And the cycle repeats, right? Lather, rinse, repeat. 

The solution is just not overbuying in the first place, especially when you are in active transformation and not knowing what the next season or the next year will bring. I really recommend buying less than you think you need to start, because you can always add more. But going overboard doesn’t really solve the problem any better, right? She couldn’t wear those 20 outfits in eight days. What’s she gonna do, a costume change in the middle of the day?

It didn’t solve the problem any better. It just required more money than she needed to spend. And you cause yourself more difficulty on the other side if all of a sudden you find yourself in a different situation. 

I am not going to tell you how many clothes you need for your specific situation. That is a question only you can answer. But for me in my everyday life, I like to have about two to three weeks worth of outfits. That’s all I really need. And it feels good not to be drowning in clothes and also wearing the pieces that I love a whole lot more.

This one requires restraint, and that has been hard for me. I will admit it. I like clothes. I think they’re fun. I work with them all day long. A lot of cute things come across my path. But getting rid of clothes that I only wore twice, that’s harder and it feels bad. And I have really had to change my mindset from thinking about what I want right now to how I want to feel next season or next year. That mindset shift alone has saved me a lot of money and it’s made my seasonal closet edits a whole lot easier. 

The fourth lesson I’ve learned from completely overhauling my wardrobe is that this is an opportunity to get the wardrobe you want, so don’t waste it. I want you to think about your closet for a minute. Chances are it contains a lot of clothes that you don’t wear often or at all, or pieces you’re not crazy about. Wouldn’t it feel good not to have those things, to only have clothes that you love and want to wear? I think this is what women mean when they say they want to start over. 

Rebuilding your wardrobe is a do-over, whether you do it all at once or it takes years. But the thing is, a do-over is only beneficial when you do better. Doing better comes from two things. Number one, knowledge. Number two, intention. Most of us have the closets we have and the wardrobes we have because things were purchased without knowledge or without intention. Knowledge means knowing what your style is. 

So you’re not filling your closet with clothes that aren’t really you, but they were a good deal, or someone on the internet said you should buy it. And knowledge means knowing the styles and colors that you feel best in. So you’re not left with a wardrobe that makes you feel blah or frumpy. I guarantee you that is not what anybody meant when they said they wanted a wardrobe do-over, right? 

Intention means that when you add things to your closet, you’re adding clothes that fill a gap or solve a problem. Intention also means that your purchases evolve your wardrobe and improve your style. It’s not just adding more stuff. 

When you buy clothes without knowledge, what you end up with is a closet full of fine. Clothes that aren’t bad enough to get rid of, but also not good enough to want to wear. And that is the closet that a lot of us have right now. 

On the other hand, when you build a wardrobe without intention, what you end up with is too much stuff in some areas of your wardrobe, usually things you like to buy, fun things like graphic tees, sweatshirts, I don’t know, cute sneakers, whatever you enjoy, and then big gaps in other areas of your wardrobe, sometimes really important areas that make it hard to get dressed. You end up with things that don’t go together and the result is a hodgepodge of cute things that don’t add up to anything. 

On my wardrobe transformation journey, I haven’t struggled with knowledge. I know what my style is. I know how to dress my body. And frankly, if I didn’t have knowledge, you should just stop listening to me right now. What are we even doing here? But that doesn’t mean I haven’t had to consciously use my knowledge in a different way. 

When my wardrobe was settled and my body wasn’t changing, the knowledge just kind of ran in the background. I didn’t have to think about it. But when my body changed and my needs changed, I found myself having to actively recall it. And like I said earlier, I had to say to myself, okay, Jen, what do you know? What do you know about what to do here? What would you tell a client who all of a sudden had hip dips for the first time in her life? And the cool thing about learning the fundamental skills of style is that they never change. You just apply them differently to your new situation. 

On the other hand, I have struggled way more with intention over the last couple of years. To be honest with you, over the years, I have earned the ability and the right to be a little bit less thoughtful about my wardrobe. And what I mean by that is that I have always had my basics nailed. I could put anything into my closet and have something to wear with it. 

I was never adding things I couldn’t or wouldn’t wear. But that has changed. I don’t know if the black dress pants I wore last year still fit. I don’t know that I have a shell to wear under jackets that doesn’t gap and sag at the neckline. So I can’t just pick up fun things when I find them and know that I can wear them. 

It used to be that everything was a sure thing and now not so much. So I have to be really thoughtful about what I add to my closet because I don’t want to fill it with things I can’t wear. That has been a huge change for me, probably the biggest change. So I want to talk about a couple of ways to rebuild or build with intention. 

The reality is, we’ve talked about this already, overhauling your wardrobe or starting from scratch is expensive. It requires a lot of energy. So you really want to be smart about it. Two ways to do that. First, do not buy ahead. I know I just told you to plan ahead, but that is completely different than buying ahead. Planning ahead is saying, In October, hey, I have a concert to go to in November. What am I going to wear? 

Buying ahead is saying, I bet I’ll be able to fit into this dress next summer and it’s on clearance, so I’ll buy it now. Or if you are in a period of job transition, it’s not buying an office dress for next summer when you haven’t gotten the job that would require you to wear that dress to an office that you’re not going to yet, right? That is buying ahead. And it is a bad idea in the best of times, but just do not do it when you are in transition. 

Here’s why. When I got pregnant with my first daughter, there was a website and community forum called The Bump. Does anyone else remember that? That’s where you got all the good pregnancy advice, at least back in 2007 it was. 

One of the first things I read on there was maternity clothes advice saying, go buy clearance clothes now because what’s on clearance now is what you will need in your third trimester. And it made total sense to me. I found out I was pregnant in October, I was due in June, and what was on clearance was late spring and early summer stuff. So that seems like a good idea. 

The advice also said, buy one size bigger than your current size to accommodate the weight gain. Great plan. We all gain weight during pregnancy, so it seemed like really solid advice. I went to Old Navy and I cleaned up. I found dresses for $10, shorts for $5. I built an entire maternity wardrobe for, I don’t know, probably 250 bucks. And at the time I was wearing a large, so I bought an extra-large in maternity.

Maternity wardrobe sorted, right? Wrong, don’t come for me. But I was a medium in maternity clothes when I gained birth. Now, don’t worry, the universe is fair. So I put on 30 pounds after I had her from the postpartum depression. But the point is, you just don’t know where you’re going to end up.

And I don’t know if you all know this, but my husband used to work for the Department of Education. Used to being the important point there. 

And last year he found himself job hunting after having worked at home for like a decade. He didn’t have suits and a corporate wardrobe anymore, but chances were he was going to need one. He didn’t know though, would it be 100% in office, hybrid, work from home? We just didn’t know.

So we didn’t go out and buy him a whole new work wardrobe. We just bought him a few interview outfits and that was it. And it was a really good thing because he ended up starting his own business and now he works in his beloved joggers full time. Buying ahead is a really, really, really great way to waste money and end up with a lot of clothes you now have to deal with. I donated every piece of maternity clothing that I bought in advance with tags still on. 

When you are in any kind of active wardrobe transition, whether that is how you spend your days or your shape, your size, whatever, spend your money solving today’s problem. Just focus on the phase that you are in right now. 

Another shopping with intention strategy is not to build a wardrobe one outfit at a time. I know I just told you that my husband bought a few interview outfits and that’s all, but that is about the phase. That is all the phase required. 

If he had to go back into an office five days a week, building a work wardrobe one outfit at a time would have been stupid, right? That would have been a lot of work. So if your phase is short, definable, and doesn’t require much, sure, buy a couple outfits to get you through. But if your phase isn’t a phase, if it’s just life, don’t do that. For example, if you move from Florida to Alaska, do not build a cold weather wardrobe one outfit at a time. Solve the problem. Solve the phase. 

One strategy that I’ve used for this is to focus on one category at a time. This keeps me from getting overwhelmed by, oh my goodness, I have to replace everything. And it also keeps me from just going and buying one outfit at a time. 

Last summer, I had no tops beyond just basic tanks. I needed some cute, beyond basic, going out to dinner kind of tops. So that’s what I went and bought. I went to the mall. I did not even allow myself to look at shorts, dresses, shoes, nothing. I was solving beyond basic tops. 

When you do that, you see everything you have, you see everything you’re buying as a whole, and you don’t buy duplicates or almost duplicates. I was at Loft and I was trying on a really cute top and then I thought, oh, wait a second. I just bought a tank with an asymmetrical neckline in almost the same color at Nordstrom. I don’t actually need this. One outfit or one piece at a time probably would have put both into my closet.

Remember, you do not need as much as you think you do. And buying with intention is the best way to end up with the wardrobe you’ve always wanted, rather than a closet filled with one-off, just fine pieces that you might have to get rid of later. 

The last lesson I’ve learned from overhauling my wardrobe, and this is probably the biggest one, is that you have to stay on top of closet editing. I think knowing what you are working with is important all of the time, but when you or your wardrobe is in flux, you have to know what you have and what you need. If you are going back to work, the time to find out that none of your tops work with your pants is not the second day on the job. Like I’ve said already, I tackle one category at a time at the beginning of every season. 

This helps me ensure that I have the basics. I just try on the entire category, get rid of what no longer works, and I fill the category with just what I need to create that fabulous functional wardrobe. And so I don’t have to get rid of too much on the other side. You know that already. 

But what I want to talk about a little bit more is my closet editing process and how I make decisions about what stays, what goes, and where it goes. None of this is intended to tell you what you should do. This is what I do. I will offer my thoughts about what to do with the things that no longer serve you in each individual episode, but it does kind of depend on the situation. Today though, it’s just me, just talking about me. First of all, I do not save anything in case I might need it or want it someday. Everybody who knows, knows that I hate the word someday. Go find it on the calendar. You can’t, you cannot.

A few reasons for that. First of all, I hate clothing management. I hate it. I hate it so much. I hate changing my closet and dresser over for the season, but that is a necessary evil because I share a much smaller closet than the one I used to have all by myself. But I’m actually getting stressed right now thinking about the bins of clothes that I would be storing if I kept everything from the last two years just in case. Also, I don’t want to wear the things that don’t fit me anymore ever again. And I want to explain this very, very carefully. 

It is not because I had terrible clothes when I was bigger and now I have wonderful clothes. No, not at all. I had great stuff then. I’ve got great stuff now. I literally grieve some of the pieces that I say goodbye to because I loved them so much and I have spent a lot of time on Poshmark and eBay trying to recreate my exact same wardrobe because one value I hold is to buy clothes I love no matter what the letter or the number on the tag says. But the philosophy of only having clothes that serve me right now means that I have to say goodbye to clothes I really love. But I do it because keeping them means that I am keeping one foot in another phase of my life. 

Either I am waiting for the other shoe to drop and gain the weight back, or I am waiting to become the person who can wear the smaller pants again. And that means never being fully present in who I am and where I’m at right now. And honestly, I don’t see the value in that. I think that this can apply to trends, lifestyles, size, shape, whatever kind of change you’re going through. 

Build a wardrobe for the person you are right now. instead of hanging on to baggage. And you’ve probably heard me say it before, your closet should be the boutique you shop from every day, rather than a museum for the person you used to be or a warehouse for the person you might become. Live in and dress for the now. And that means that I get rid of clothes that I love, that I might have to buy again someday on the other way up the scale. I don’t know. I don’t know where I’m going to end up. I just know that I’m focused on right now. 

On a more practical note, along with my quarterly category edits, I also have a laundry basket in my closet where I put things as I go about my daily life. I put on a pair of pants the other day that I had not worn in a year. They were wide leg back then and they are ridiculous like now. I don’t need to wait until the day pants get edited to pull them out of rotation. I already tried them on. Why would I hang them back up just to do it again? I also keep a note in my phone where I put specific items to replace, like gray Zara flannel trouser, right?

If I love it enough to want to go find it, I will be super-duper duper specific about it. Or I will just put categories. If I had tried on that pair of pants and they didn’t work and then I tried on all the others and they didn’t work either, I’ll just add that to the list. Those are both things that I have done for as long as I can remember, but now they are so much more helpful and so much more important. 

Also, I think it’s important to have a plan for what you’re going to do with the clothes that no longer serve you. Are you going to try and tailor some things? Are you going to sell them on Poshmark or ThredUp? Are you going to donate them or recycle the things that aren’t nice enough to donate?

Don’t let it get to the point where you have bags and bags or bins and bins of stuff to deal with. It is overwhelming at that point. And one thing I’ve really learned is the smaller chunk you have to deal with, right? Whether that’s buying, editing, donating, replacing, whatever it is, the smaller chunk you have to deal with, the easier it is. 

The last thing I wanna share with you today is how I decided what stays and what doesn’t right now. Obviously, my biggest reason for getting clothes right now is fit. And I am a big believer that if you don’t have fit, you don’t have style. Thank you, Stacey and Clinton for that one. 

So for me, it’s pretty cut and dry. But I do want this to be valuable for you as well, regardless of the reason for your wardrobe transformation. So very quickly, here are five good questions to ask yourself when deciding whether or not that item is worthy of taking up a hanger. 

One of our members coined that phrase years ago, hanger worthy. And I just love it. Like every hanger in your closet is valuable. And only things that are worthy of a hanger get a hanger.

 So anyway, here are five questions. Number one, do I really like this just as it is? If you’re like, oh, I’d like it if the color were different or if it had a different neckline, you don’t actually like it. Let it go. This is another way of asking, would I buy it again just as it is? If the answer is no there, you probably don’t like it enough to keep it.

Question number two, do I feel good in this? You can love an item of clothing until you put it on your body. Clothes that you only love in the closet don’t serve you. And there’s nothing that is going to magically change. It’s not like the clothing fairy is going to come in and change things at night to make them different, right? Get rid of it. 

Number three, what problem or need does it solve in your wardrobe? I am not huge on this idea that if you haven’t worn it in a year, get rid of it. I don’t think you should keep a ton of stuff just in case, but don’t get rid of the dress that you wear to funerals just because you haven’t had to reach for it in a year. Like that’s actually a good thing, right? If you still like it, you still feel good in it, you still would buy it again, I would not ditch it.

Number four though, do I have something I reach for instead? If you are hanging on to that funeral dress just in case, but every time you could have worn that dress, you didn’t pick it, you wore something else instead, that is super telling. It’s not that important in your wardrobe. And chances are there will be no clothing emergency that requires you to wear the thing you don’t like as much as you like the other thing, right? 

Number five, finally, can I afford to get rid of this right now? This is a strategy that you need to use very, very sparingly and very, very intentionally, because if you allow this to overtake everything, you’re just going to be right back to where you started. But there were times with my clients, and it’s happened in my own closet, that we have left some of the best of the worst, for lack of a better phrase, because if we didn’t they or I would have nothing. 

Case in point, last winter, my pajamas were getting too big, but my jeans were too big, and my skirts didn’t fit, and none of my pants fit. It was just so much at one time. And I looked at everything I needed and said, okay, pajamas are just gonna have to wait. I didn’t love doing it. You know, I find the value in having nice things that most people don’t see, but there are practical realities. This year, I don’t need as many real clothes, so the PJs got an upgrade. 

Again, not everything can be a placeholder until you find something better, but sometimes you need to prioritize and that’s okay. This is real life, not just a theoretical article about how to have the perfect wardrobe at all times.

All right, your homework for this episode is to take a look at one category in your closet, just one, preferably the one you know isn’t working. Figure out what you have, what still works and what you might actually need. Use my five questions and remember that you cannot build great style out of a closet full of fine pieces. 

That’s all I’ve got for you today. Hopefully my seasons of upheaval have been useful to you. If so, it will all have been worth it. And if you wanna learn the skills that make navigating change so much easier, I invite you to come join me inside of the Style Circle.

I will see you next time, and until then, remember that your everyday matters, so get dressed for it.