Jennifer Mackey-Mary: Hello Gorgeous! 

It is week 9 of The Everyday Style School: Summer Shorts–our weekly summer series sharing a quick style thought or  tip to help you save money, save time, and get the wardrobe you’ve always wanted.

I’m your host, Jennifer Mackey-Mary. I’ve been dressing women for 25 years, and I’m on a mission to help you love the way you look every day. 


Today’s tip is a practical strategy that will help you love the way you look more often, and that is, Spend your money where you spend your time.

One of the clients I worked with early in my styling business was a woman who wanted help looking more put together in her daily life. We didn’t do a closet edit, because she said she had nothing, she was really struggling everyday, so there was no point–we just needed to start from scratch. Ok, cool, we can do that. 

We met up for our shopping trip, and were strategizing before we got started–talking about her budget, items she absolutely needed to get, and some things she hoped to find if time and budget allowed.

Her budget for the shopping trip was $500, which isn’t nothing, but she was expecting this to be her big wardrobe shop for the year–and in that context, $500 isn’t much, especially if you’re starting from scratch. There were a bunch of things on her must-have list, but two really stood out–First, jeans. She was a self-described jeans and tshirt woman, and she said she lived in jeans, but she only had one pair, and she didn’t really like them.. Ok, no problem, that was where I started with 90% of my clients. The other must have piece was a dress for a black tie event she and her husband went to every year. I don’t remember what it was–I think it was something for a charity that was really important to them. Doesn’t really matter. 

I asked her if the dress was part of the budget, or in addition to, and she told me it was part of it. She had already factored that into the $500 she felt comfortable spending. Now, I was always very respectful of budgets, and I love a challenge, but in my head I was like, there goes the nice to have list, and most of the need to have things, too. I explained to her that $500 probably wasn’t going to go as far as she’d hoped, but we’d do our best, and then we talked about budget in a little more detail, and how she wanted to allocate her dollars. She told me she was comfortable spending 2-300 on the dress—this event was really really important to her and her husband and she wanted to look great for it. Then she told me she was comfortable spending around $30 on jeans. Definitely no more than $50. She told me this was how she’d been doing in the past and it was working for her. 

Obviously the fact that I was there having this conversation meant it wasn’t actually working for her, but that’s not the point. The point is that this was an important lesson for me as a stylist, because I was still learning the common mistakes women were making in their wardrobes, and how to fix them. A little lightbulb went of in my head and said “of course she cant’ get dressed–she’s got no money for anything else, and can’t invest in nice things”

This client was an extreme example–but since then, I’ve worked with countless women who were doing the same thing to varying degrees, leading to various levels of struggle…but the problem was the same–there was a disconnect between where their wardrobe dollars went, and how they actually lived their lives.

There are two parts to the idea that you should spend your money where you spend your time, and today we’re going to talk about both of them, as well as how to rightsize your wardrobe so you can like the way you look more often, and stop wasting money on clothes that aren’t worth the investment.

The first, and often the most obvious issue I saw was that my clients didn’t have enough clothes for the way they really lived. It’s a quantity problem Take my client, for example–she was a self described jeans and tshirt woman, but she only had one pair.. 

And you know that whole “A closet full of clothes, but nothing to wear” thing? I can’t tell you how many times I heard it, or saw it, but the issue was rarely that my clients truly had nothing, it’s often that they had too many things for some parts of their lives, and not enough for others–specifically, they had too much stuff for things they didn’t do all that often, and not enough for the things they did all the time. 

I often say your wardrobe isn’t all the clothes you own, it’s all the things you can, and do wear. So yeah, you might have 20 pairs of dress pants for work–and that’s a lot, but they don’t help you if you’re working from home and want to be comfortable–that’s an example of too much of the wrong thing.

On the other hand, I’ve worked with women who struggled to get dressed for zoom meetings because they didn’t have tops that looked polished and work appropriate, but not too dressy, because no one believes you’re wearing a blazer in the comfort of your own home, right? I remember asking a client how often she had zoom meetings to get an idea of how big this issue was–and she told me that was basically her job..She had them every day. She was rotating through 3 tops and was getting the feeling that it was becoming noticeable to her clients–this is an example of not having enough of the right thing. 

That’s the first part of spending your money where you spend your time–making sure the distribution of your wardrobe roughly matches the distribution of your time. 

The other part though, is about the quality of the right things. What I’ve seen a million times over the years is women willing to invest in really special pieces, but going as cheap as possible when it comes to their everyday wardrobes. Let’s go back to my client. She was willing to spend 40-60% of her budget on something that would be worn a few times at most, but wanted to spend no more than 10% on the piece that DEFINED her style. If you describe yourself as a jeans and a tee woman, shouldn’t you be buying good jeans? 

I think this all goes back to looking at our everyday lives, and by extension, our everyday wardrobes as placeholders until the good stuff comes along. 

I remember working with a client who was feeling frumpy and kind of intimidated by the women in her neighboorhood–which, fair–we didn’t live in the most come as you are, no judgement here kind of place. But she was struggling because she lived in athleisure clothes–leggings, sweatshirts, tees, and didn’t want to give those up. They were practical for her life. She didn’t understand why she was wearing the same things as the women around her, but they looked put together while she didn’t. She figured maybe she just didn’t look good in athletic clothes, and needed to dress up more. But when we went through her closet, that wasn’t the problem at all. The problem was that all of HER athleisure was low quality to begin with–and then had been worn to death. Everything was faded, stretched out, pilly…it just needed a refresh. When we went shopping, we were NOT limited by a tight budget, so I took her to athleta, knowing we could find some nicer athleisure there. She had total sticker shock and kept saying things like “I’d never pay that much for leggings”, and “I’m not walking the dog in a hundred dollar sweatshirt”. The price tags were personal that day. I convinced her to try a few things on, and they looked amazing on her–they had better shape, structure and style than what she had been wearing, and she admitted that she wouldn’t feel out of place in those things. But then she said “we can find things like this cheaper, right”. At that point, I asked what was up, because while I was very respectful of budgets, we’d already been to nordstrom where she’d spent over a thousand dollars on 2 pairs of jeans, a few pairs of shoes and a couple of tops. So it wasn’t like she couldn’t spend a little more, right? She said she just couldn’t see spending that kind of money on clothes that didn’t really go anywhere. Obviously, this was a mental block, so I started asking, how many days each week do you wear jeans? Maybe one or two. How many days a week do you wear ballet flats–I’m usually in my sneakers. Where have you gone in the last week–kid stuff, coffee, errands. What did you wear? Leggings and a sweatshirt.

Finally I was like, do you see that the majority of your life is spent in leggings and sweatshirts, and you wear leggings and sweatshirts to the majority of places you go–so these clothes DO go places. She agreed, And so I said, tell me how it makes sense to be in the worst clothes the majority of the time? Here’s the part where I would love to tell you that she saw the light, and we bought lovely athleisure things, and she lived stylishly ever after, but that’s not what happened.

Nope, what happened was she said “I can see that, but I just can’t”. I tried my best. She just couldn’t accept that these unexciting places, and routine activities were worthy of nice clothes. For her, they were just placeholders until her real life started.

I want you to Try something with me for a minute, and imagine yourself in the middle of a circle–that’s the way you spend the majority of your days. Now around you are some other smaller circles. These are things you do, but not as often. Maybe going to concerts, or traveling, or to fancy brunches–whatever, they’re you’re circles. You can buy nice things for all of the smaller circles, but if you neglect the middle circle–the biggest one, you’re missing the opportunity to look nice the majority of the time. Make that make sense!

When we’re afraid, or unwilling to invest in better things for the way we really live the quality of our wardrobes suffer. Quality means a couple of things here. Actual clothing quality–like the construction and longevity, as well as  the visual quality, or style. 

Clothing Quality isn’t always a given–I have a lot of issues with the quality of today’s clothing one is that often, you don’t get better quality if you spend a little bit more–you have to spend A LOT more to really see a difference, but there are things that investing a little more will get you better quality, especially in jeans and shoes. 

When it comes to style, or visual quality though–a little more money almost always gets you a little more, or a little better style. I find graphics to be a good example of this–like graphic tees and sweatshirts. MOST OF THE TIME, not always, but very frequently, the cheaper the item, the cheesier the graphic. The more expensive the item, the more stylish the graphic. Again, I’m not saying all cheap graphics are terrible, and all expensive graphics are great–not at all, but if you want an easy way to stay on the cool and quirky vs corny and chessy side of graphics, invest a little more.

Another way style is impacted, and this is what I see most often, is that everything can get super basic when you spend as little as possible. My athleisure client had plain leggings, plain tees, plain hoodies, plain sweatshirts. Nothing had any interest. You know I love sweatshirts, and I’ve got basics from Old Navy and gap–and there’s nothing wrong with them, but my most stylish versions are not. Those are from anthropologie, nordstrom, boden, evereve, marine layer...None of those were $20, and yet, they’re some of the best money I’ve spent. Because not only do I feel like ME in them, I feel like the best version of me. An elevated version. And they’re not things I’ve been able to get inexpensively. Trust me, I’ve tried.

Part of spending your money where you spend your time comes down to cost per wear–I don’t hesitate to spend on sweatshirts, because I know I’ll wear them and get my money’s worth, unlike fancy dresses that would only be worn a handful of times, but part of its just wanting to feel as good as possible as often as possible, and if that means spending more, it’s worth the investment.

So here’s what I want you to do if you’re ready to feel as good as possible as often as possible too. 

First, you have to accept that the places you go most often and the things you do most frequently are in fact your real life. They’re not simply filling time until something better comes along. Once you accept that, you can decide if you’re ready to invest a little more in it or not, but if you keep buying clothes for fancy dinners out, but you haven’t been to a nice restaurant in years, you’re going to keep filling your closet with the wrong stuff, and not have cute outfits to go to Chick Fila a in. 

Then, figure out if your issue is in the quantity of clothes you have for your real life, or in the quality. Here’s an easy way to tell. If you struggle to get dressed its probably a quantity problem. If you can get dressed just fine, but you’re underwhelmed with the results, chances are its a quality problem. 

Finally, solve the right problem. If its quantity, ask yourself what would make it easier to get dressed. More jeans? Are you missing layers? Do you need shoes?

If it’s quality, start by just looking at nicer versions of the things you love to wear. So if it were me, and I wanted sweatshirts, instead of looking at Old Navy’s options, I’d look at Nordstrom or Anthropologie. If you find something that lights you up, and it’s in your budget, give yourself permission to splurge a little. If you’re having a hard time justifying it, look on Poshmark or Ebay. That can be a great way to test the waters of buying better.  

It can be hard to change your thinking about spending on everyday clothes instead of special things, but I know that when you start to feel more stylish, more often, it’s an easy practice to keep up with, and over time, you’ll find you’re wearing more of what you own, and spending less on clothes you never reach for.

Oh, and in case you’re wondering what happened to my client who wanted to blow 60% of her budget on a single dress for a single evening, I found her a fabulous gown on clearance for under a hundred dollars, and then put her in the most expensive pair of jeans she’d ever worn. She emailed me to tell me that after our shopping trip, she bought two more pairs. That, my friend, was money well spent. 

That’s all for this episode of Summer Shorts. I hope it inspires you to rightsize your wardrobe, and invest in clothes for the way you really live. It’s true…your everyday really does matter, so get dressed for it. Thanks for listening, and I’ll see you next week.

Jennifer Mackey-Mary [outro]: And that's a wrap. Thank you for listening today. If you're loving the Everyday Style School podcast, I'd like to invite you to become a member of the Style Circle. It's our monthly all-access membership that gives you everything we create to make style easy, so you can save time and money, have easier mornings, and more confidence all day long. You get our seasonal capsule wardrobe guides, all of the masterclasses we offer, and our exclusive members-only podcast, The Everyday Style School Extra Credit. Plus, you're invited to the Facebook community, where you can get even more style support and inspiration. I would love to get to know you and support your style journey. It's just $19 a month, less than the cost of a clearance shirt you're never gonna wear. Come join me and make your everyday style easier.