Have you ever found yourself stuck in a cycle of spending money and buying clothes, but still struggling to get dressed? It feels like no matter what you buy or how much you buy, you either still don’t have the right pieces, or it all ends up looking the same. Either way, you didn’t solve your wardrobe problem.

It turns out there is a simple tool that can help you get off the hamster wheel of spending and struggling, and today I’m going to share it with you. Let’s get started.

Hello, gorgeous. Welcome back to the Everyday Style School, the podcast that gives real-life style advice to real-life women. I’m your host, Jennifer Mackey-Mary. I’m a wardrobe stylist who’s been dressing everyday women for over 20 years, and I’m the founder of Everyday Style, where we’re on a mission to inspire women to love the way they look and give you the tools to make getting dressed easy.

Friends, one pattern I’ve noticed in my career — both in my one-on-one stylist days and now as a course creator and podcaster — is that more shopping and more spending don’t always add up to more to wear. Often the clothes you buy just make things worse, because you’ve spent your money, you’ve added to your closet chaos and overwhelm, and you’re still struggling every day. Over the years, I’ve probably said one million times that you don’t need more clothes, you just need the right clothes. And that is true. But how do you know what the right clothes are? How do you know what you actually need? And how can you stop yourself from wasting money on the wrong things?

Well, my friend, it turns out the secret to buying better is a magical little tool that I like to call a shopping list.

I don’t know if you are the grocery shopper in your family, but I am. And every weekend I make a grocery list. That little piece of paper keeps me from buying things I don’t need, and ensures that I buy the things I do need to make somewhat delicious, mostly interesting dinners all week long — or my husband can make delicious and interesting dinners, either way. But without that list, I would probably have stockpiles of things like pasta and cheese, and I would probably forget things like red pepper flakes or diced chilies. Then all week long I would struggle to put dinner on the table, and my whole family would be less than happy.

The other thing my list does for me is it keeps me from buying dumb stuff I really don’t need or won’t use. A list is the secret to not wasting money, but also to making it easy to make dinner every night. And hopefully you’re seeing the parallels between my grocery list and a wardrobe shopping list, right?

Today we’re going to talk about how to create a shopping list that helps you buy the right things, stop buying the wrong things, and one that makes it easier to put together fabulous, interesting outfits all week long. I’m going to share some questions that will help you build your list, and then we’re going to talk about how to prioritize that list if buying it all at once isn’t realistic — which it isn’t for most people.

The List Itself

But before we get to that, I want to talk about the list itself.

Many, many months ago, I was talking to a woman who was struggling with her style. She had too many clothes, not enough to wear — a story I’ve heard again, one million times. She was telling me how she loves to shop and packages arrive a couple of times a week. Again, not an uncommon situation. We talked for a little bit, and my services just weren’t a great fit for her. But I suggested that she could make her shopping more effective by making a shopping list.

She had a hundred questions about the list. Like, does it need to be an actual paper list? Because she was pretty sure that she couldn’t keep track of that. I said, no, if a paper list works best for you, great. Otherwise, you could put it in the notes app on your phone, or if you’re good at remembering things, you could just keep it in your head. She told me a list felt too limiting, like it would take all the fun out of shopping — which, okay, fine, whatever. I did not mention to her that she was currently reaching out to a wardrobe stylist to spend money on, because she wasn’t having a whole lot of fun getting dressed. But I said the list doesn’t have to be super rigid, it doesn’t have to be super specific. It could just be general categories of what you’re looking for, to guide your shopping.

Then she wanted to know what she should put on her list. And this time I did say, I can’t help you there, because everyone’s list is going to be different, because everyone is different and we’re all starting with a different wardrobe. Everyone’s needs and style are different. You have to do the work of creating your list yourself. She, of course, wanted that wardrobe must-have list — just tell me what to buy and I’ll buy it. I simply don’t believe in that. Generic must-have lists are a really great way to spend money on clothes that you’re never going to wear.

In the end, she was not a fan of the list idea, and I felt very secure in the fact that she and I were not the right fit for each other. But it did give me the idea for this episode, so I will take that as a major win.

Point being, though — the list can be anywhere, in any format that works best for you. On paper, on your phone, in your head. It doesn’t matter, as long as you remember the things on it. I’m a fan of the phone — I know I will always have it when I’m at a place that sells clothes. And to be honest with you, my memory just ain’t what it used to be.

Your list can be as specific or as general as you want it to be. You can list an oversized light gray turtleneck sweater to wear with your leather pants, or you can put “warm sweaters” on your list. That’s up to you. One thing that’s always on my mental list is casual knits that look nice on camera — very general, because it would be impossible to describe exactly what they look like, right? I’ll just know it when I see it. But sometimes I’ll have something as specific as an olive utility blouse on my list. It just depends. Don’t overthink it. The point of the list is to guide your buying and make sure you’re adding things to your wardrobe that make it easier to get dressed, instead of just wasting money and adding to closet overwhelm.

Six Questions to Build Your List

So now let’s talk about what to put on that list, or rather, how to know what to put on the list. For this, I want you to ask yourself six questions. It’s kind of a lot of questions, so I’m just going to go through them pretty quickly. Ready?

The first one is: what have you struggled to get dressed for? This is one of my favorite style questions to ask clients, because it immediately identifies wardrobe holes. If I asked you right now, what does your wardrobe need, you might struggle to think of something. But if I asked you about a time that you struggled to get dressed for a specific event, you could probably come up with something pretty quick. Now, I follow that question up with, well, what did you wear? How did you feel? And what do you wish you would have worn instead? I want you to do the same thing. Think about specific times that you stood in front of your closet and struggled to put an outfit together. Maybe it was for a work meeting, or a girls’ weekend, or a wedding. What do you wish had been in your closet that day? Do you wish you would have had a fabulous suit, or a fun top, or a pretty dress? Put those things on your list. Chances are those events, or similar ones, will come along again, so be ready next time.

In my Style Struggles episode I did recently, I talked about how I struggled to get dressed for special things, especially in the summertime, so I had to put some dressy, non-work-y statement tops for summer on my list. Next summer, I will be ready.

Now, if you struggle to get dressed for everyday life in general — hang on, we’re going to get there. I’ve got some questions for that too.

The second question to ask yourself is: what do you like to wear, and how can you diversify it? One of the biggest shopping mistakes I see women make is buying the same things, or very similar things, over and over. This happens when you don’t have a list and you go into default mode. It’s the reason I would have a million boxes of pasta if I was grocery shopping all willy-nilly — it would be my default, I know it’s easy, I know I can make it taste good, so that’s what I would buy. It’s the same with clothes.

First, ask yourself what you like to wear. If you’re a jeans-and-sweatshirt person, cool, start there. But then we’re going to broaden the ideas. So if you’re a jeans person, check your closet — do you have all straight-leg, mid-wash jeans? That’s probably your default position. Start by just diversifying the silhouettes and washes. Now, if you already have different types of jeans, ask yourself what you like about jeans, and then add things that serve the same purpose to your list. So if you love the easy, casual, can-dress-it-up-and-down, five-pocket styling, add a pair of cords or leather jeans to your list.

If you love wearing dresses, start there. If they’re all fit-and-flare midi dresses, start by diversifying the silhouettes. Then ask yourself why you like dresses — what is it about them that you like? If it’s the one-and-done easy styling, maybe add jumpsuits to your list, or matching sets that require no effort to style. This is going to help you buy clothes you’re going to want to wear that still look different from what you already have.

Question number three is: how do you spend your time, and does your wardrobe reflect that? If your life used to be working in an office, so your life was like 50% casual, 50% dressy, but now you work from home most of the time and it’s 80% casual, 20% dressy — does your wardrobe reflect that change? If not, you may need to add some casual pieces to your list. You should always spend your wardrobe dollars where you spend your time. It might be super fun to buy pretty dresses for fancy brunches, but if you don’t go to any fancy brunches, your dollars will be wasted, your closet will be packed, and you will still struggle to get dressed.

Along with this, I want you to give yourself permission to spend money on the clothes you really wear, for the life you really live. I see so many women not investing in things like jeans and athleisure clothes and casual tops because they’re not going anywhere special. Meanwhile, they’re wearing those types of clothes 90% of the time. I hate to break it to you, but this is your real life. This is it. You should have the nicest things for the way you spend the majority of your time. I’m not telling you you need to go buy a $700 hoodie from Off-White to run errands in, but give yourself permission to invest in your real life.

Question number four is: what would make getting dressed every day easier? This is less about those specific occasions where you stand in your closet going, oh my gosh, I’ve got nothing, and more about the little struggles that add up every single day. If all of your pants are the right length for flats, and anytime you want to wear heels they’re too short, add a pair of longer pants to your list. If you’ve got a great collection of cardigans and jackets, but you struggle to wear any of them because you don’t have the right base layers, put some basic tops on your list.

I’m going to tell you a little sidebar — that is the thing I saw most when it came to tops. Women love to collect cardigans, but they don’t have enough to wear under them. So look there. Look for what I call wardrobe roadblocks in your closet — these are things that stop you from wearing things you already have. In my experience, this is almost always in the bottoms. Women either don’t have enough bottoms, or not nice enough bottoms, or bottoms that fit, and that makes getting dressed every day really, really challenging.

Question number five is: what would make my outfits better? Maybe your wardrobe is stocked with great basics and getting dressed isn’t a struggle, but the results are just sort of underwhelming. If that’s the case, when you get dressed, look at your outfit with a critical eye and ask, what would make this more exciting, more interesting, trendier — however you want to look? This is a really great time to bring in your style guidepost that we teach in our Signature Style masterclass. When you know how you want to look, it’s easy to know what to buy, which makes your list way more effective. But if you’re standing in the mirror in a black sweater and jeans, what would make it better? Maybe an updated jean style, or a little texture to the sweater, a belt, a more interesting pair of shoes. Are there trends you would like to try? This question is really about fine-tuning and up-leveling your style, and it’s an ongoing process — which is why you’ll probably always have at least a mental shopping list.

The last question is: does anything need to be upgraded or replaced? This is another time when looking at your outfits with a bit of a critical eye every day is really important. Sometimes clothes get ruined or shabby quickly, and it’s easy to see — like you get a stain on your favorite top and you can’t wear it anymore. But often, more often, things wear out slowly over time. It’s like when my girls were babies, and one day I’d look at them and they’d look completely different. Do you guys remember that, if you’re a mom? They didn’t change overnight, it was just that those little imperceptible changes all of a sudden added up.

In the same vein, the other day I pulled out a sweater that I wore on repeat last winter. It was my favorite. And with my fresh eyes, that hadn’t looked at this sweater for months, I was like, what on earth was I thinking? It looked terrible — it was pilled, the cuffs were getting frayed. I was a little embarrassed that I hadn’t noticed it was getting shabby last year. It was just with my fresh eyes that I noticed it. So I put a new camel sweater on my list immediately.

For me, white tank tops are a one-season thing. I’m a big fan of sunscreen and self-tanner, so they get stained and dingy so quickly. I know that every summer I need to put a few on my list. When your clothes have faded or peeled or lost their shape — whatever, beyond what you can repair or clean — it’s time to put them on the list and replace them.

Another thing to consider is updating and upgrading the things you wear often. Again, if you are someone who wears jeans all the time, is it time to upgrade your jeans, either to a higher-quality pair or even a more current style? Styles have shifted so much over the last three or four years that there could be pieces in your wardrobe that don’t work as well with newer silhouettes you’ve added, and that creates a wardrobe roadblock — the pieces just don’t quite work together to make outfits anymore. If you’re noticing that some items could use an update or an upgrade, put them on your list.

Now, I’m sure that’s not an exhaustive list of questions to ask yourself, but those six will help you identify wardrobe holes for both everyday and special occasions, as well as wardrobe roadblocks that keep you from wearing the clothes you already have.

Prioritizing Your List: Needs, Wants, and Nice-to-Haves

Okay, now that your list is as long as your arm and you’re thinking you’re going to have to sell a kidney or your first child to buy all the things on it — hold on. Before you call the black market organ broker, let’s prioritize that list instead.

We’re going to break down your list into three categories: needs, wants, and nice-to-haves. Two things determine which category the things on your list will go into. First, the level of urgency with which you’ll want to check that item off the list. And second, whether it is something that you need to hunt for, or if it’s an item you should gather instead. I’ll explain more as we get into the categories.

Your needs are exactly that. If there’s something missing from your wardrobe that stops you from being able to get dressed or utilize the things you already have, it is a need. This could be like you’re starting a new job and you’ve got nothing appropriate, or you’ve been invited to a wedding and you’ve literally got nothing to wear. Those are needs. Again, if you’ve got cardigans and jackets but nothing to wear under them, that’s a need. Wardrobe basics — those staple wardrobe workhorses that you rely on every day — I would also put those in the need category. The faster you can fill these wardrobe holes, the better. That is the urgency part.

Now, here’s the hunting-versus-gathering part. These are the pieces you hunt for. You actively seek them out. You’re probably not going to find them in a fun little boutique on a day out with your friends, or on a clearance rack. For women who mostly gather, this is why their wardrobes are often missing key pieces that make it easy to get dressed. Nobody goes browsing or window shopping and comes home with a great bra, or the perfect black pants that cost too much money but are worth every penny. Those you have to hunt for. So your needs category is high urgency and high in hunting.

Now let’s talk about wants. These are things that make getting dressed each day better. Like, you can get dressed, but you want to try a new trend, or you want to upgrade some pieces that are still in good enough condition to wear, you just want something more updated or better.

Let’s use winter coats as an example. If you don’t have a winter coat and you live in a place that’s cold, that’s a need — that is urgent, and you’re going to have to go find one. Okay, so let’s say you bought a nice coat and it works, but it’s a little bit dressy, and you’d like another one that’s a little more casual. That is a want. Wants are medium urgency, meaning you don’t have to check that item off your list right away, but you don’t want to wait too long either, especially with trends — you want to get it while it’s still trending. Wants are sort of half hunting, half gathering. You’ll probably need to approach filling these missing pieces with some intention, but you can take a little more time. You can browse a little more, check out the clearance racks, wait a little longer for the right thing to come to you, rather than being on a total mission to find it.

Finally, we’ve got the nice-to-haves. Nice-to-haves are a step down from wants in terms of urgency and hunting. These are pieces that you can and should take your time to buy, and in this category, I really believe you’ll know it when you see it. In my experience, the harder you try to fill these pieces, the worse the result.

Things in the nice-to-have category include things that you love to buy but already have enough of. I have enough sweatshirts, my friends. I truly do. I love them. But if I find one I love, you better believe I’m going to buy it — I absolutely should not be hunting for them.

Another thing I would put into this category is special or statement pieces. One mistake I have seen a lot over the years is women seeking out — a.k.a. hunting for — fun clothes. I remember a client I had; she was an attorney who worked in a pretty buttoned-up environment, which matched her personality perfectly. She was reserved and quiet. But when we went through her wardrobe, she had all of these shells for under her suit jackets that were wild colors and loud prints, and they just didn’t seem like her. I asked her about them, and she said she needed to add some fun to her wardrobe, so she went on a mission to find fun clothes. I asked her, are these fun to you? And she said she always felt out of place wearing them. I was like, yeah, probably.

When we shopped, as I always did, I told her my job was to pull things that she needed, and her job was to look for things she liked. She came to the fitting room with a whole bunch of tops that added the element of interest to her wardrobe that she was looking for, but the pressure to find fun clothes was off. In the end, she ended up with things she liked and felt like her. When you go hunting for fun, you will never find it.

Going back to my Style Struggles episode and my need for non-work-y tops for summer — could I go on a mission to find them? Probably, but I will be a lot more successful if I’m simply aware that that’s a wardrobe hole I need to fill, and then just wait for the right things to come along. Just be open, and let those nice-to-haves find you.

If you take one thing from this episode, let it be this: don’t gather your needs and hunt for your nice-to-haves. You will end up struggling to get dressed, because your foundations will never be filled properly, and you’ll waste a ton of money on clothes you don’t truly love. Flip the script and hunt for your needs, and gather your nice-to-haves.

The last thing I would put into this category are highly specific items. The reality is, hunting for them is probably a waste of time, and for the most part, highly specific pieces are probably a version of something you already have. Let’s go back to our coat example. A winter coat is a need. Another, more casual winter coat is a want. A mid-calf, single-breasted, relaxed-fit coat in just the right shade of camel is a nice-to-have. It would be an absolute waste of time for me to pore over websites hunting for this coat. Trust me, I’ve tried. But if I find it, I will buy it. Until then, I’ve got plenty of other options.

The last shopping list tip I want to share with you is that you don’t have to check off your needs before moving on to your wants, and finish your wants before you buy anything from your nice-to-haves. While your needs should take priority, because it’s going to help you the most and have the biggest impact, if you find something on your nice-to-have list, you don’t have to wait. It’s more about understanding which pieces will make the biggest impact, which pieces you should go looking for, and which you should let the universe bring to you.

Wrapping Up

Now, hopefully, as you’ve been listening to this episode, you’ve been making a mental list of some of your needs, some of your wants, and some of your nice-to-haves. Pro tip: get that list out of your head and onto paper or into your phone as soon as you can. I have a million good ideas every day, and I only remember like one — so don’t be like me. Write it down, put it somewhere.

A shopping list can be such a powerful tool when it comes to creating a cohesive wardrobe that makes it easy to get dressed while saving you so much money. So I hope that you will consider using one. Just try it out — I promise it does not take the fun out of shopping. If anything, it gives you direction where you need it and freedom where you want it. And I don’t know about you, but that sounds pretty fun to me.

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If you have not taken the 2024 style survey, it’s still open for a little while longer. Share your thoughts with us on all things style related, and you could win gift cards to your favorite stores to help make a little progress on your shopping list. I love reading your responses, and I cannot wait to share them all with you. The link for that is in the show notes.

Also, head to the show notes to see how 10 wardrobe basics can create over 30 stylish outfits in our 10-Piece Style Solution. In this absolutely free guide, we will show you the 10 pieces you need to make it happen, the outfits they create, and you get a linked database so you can shop the pieces in a variety of sizes and price points.

That’s all for today. I will see you next time, and until then, remember that your everyday matters, so get dressed for it. And that’s a wrap.