Jennifer Mackey-Mary: Cladwell, what should I wear today? What’s my body shape, Gemini? Hey ChatGPT, make me a Capsule wardrobe! These days, AI is everywhere, including our closets. From apps that help you organize your wardrobe to all-knowing platforms that seem to be able to answer ANY question, style help has never been easier, cheaper, or more accessible. But how good is it, really? And can it truly help you improve your style? That’s what we’re talking about today, so 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!
Before we get into today’s topic, I want to acknowledge that AI is a hot-button issue. Some of you love it and use it all the time. Some of you hate it and think it will be the downfall of our society and water supply.
No matter where you stand on the topic of AI, I think we can all agree it’s out there–it’s being used…there’s no point in ignoring it. If you love AI, I’m not here to tell you you’re a bad person and you should stop using it. If you hate AI, I’m not telling you you’re living in the past, and you need to start using it. I am not unaware of the issues surrounding it, I’m simply taking a look at how it's being used in style, and giving you my honest, admittedly biased take on the topic…what you do with that is up to you.
This is a topic I’ve wanted to do for well over a year. The idea came to me one night, when I was mindlessly scrolling TikTok and saw a video that said “What is the most unhinged thing you’ve used ChatGpt for–tell me in the comments”. You guys, I probably read those comments for a half hour–there was some crazy stuff in there. Someone said he and his wife used it as marriage counseling. They met at the same time every week, gave it a prompt, or recapped a fight they’d had, and let ChatGPT fix their marriage. Someone else said they used it to hypothetically plan the perfect crime, just in case they ever need to. And one comment said, “I use it to create a Capsule Wardrobe every season. It’s great!”
After all the crazy stuff I’d just read, that was the one that stopped me in my tracks.
I guess I kind of thought that what we do, especially with our Capsule Guides, required a human touch. An entire team works on this thing to choose a palette that’s current and in stores, and include trends our women would actually, and reuse some pieces we’ve used before…like our process is actually very thoughtful, and didn’t seem like something a computer could just spit out in 30 seconds. But there I was, with this pit in my stomach, like, well–that’s it, I guess it’s over… we’re all getting replaced by the machines. It was the literal definition of doom scrolling - because I was scrolling, and ended up feeling doomed.
I moved on, and watched some videos of cute golden retrievers or something, and kind of forgot about it, but later that week, I was sitting at my desk, and I was like…lemme just see what happens. So I opened ChatGPT and told it to create a capsule wardrobe for me. I gave it a couple of guidelines and hit enter. The results gave me a pretty good sense of job security, and I kind of forgot about it.
In the months that followed though, I started seeing AI creep into the style realm a lot more, and when I planned the episodes for this semester–talking about ways to make the everyday habit of style easier, I figured this would be a really good time to dive in to some of the ways I see AI being used–and to answer two questions–can Ai make style easier, and can AI actually improve your style. Let’s be clear, these are two different questions. You can get dressed in 2 minutes but hate the result. That’s easier, not better. Or you can spend lots of time perfecting your outfit–choosing the perfect shoe, trying different accessories–the result is better, but not easier. Most women I know want both. We want it to be easier to get dressed, and we’d like to truly have good style. That’s the goal, right? Can AI help you do both? One? Neither? That’s what we’re on a mission to discover.
So there are sort of two sides to AI in the style world that I want to talk about –first, we have the apps. Dressly, StyleDNA, Cladwell, Wearing–that kind of thing. You see them advertised on your social media feeds all the time, even if you didn’t realize they were ai style apps. Then we have straight-up AI platforms like ChatGPT, Gemini, Claude. I want to give some pros and cons to both, and share my thoughts on AI in general when it comes to helping you improve your style, and like I said, from there, you can decide if you want to use it or not.
This was supposed to be one quick episode, but as I got into it, I discovered I had a lot to say, so I decided to break it into two parts. In this episode, we’re going to talk about the apps. In the next one, we’re going to talk about the Large Language Model platforms, like ChatGPT
Let’s get into the apps. I’m not going to list all of them, and I’m not going to review them one by one; in fact, I want to be super transparent that I don’t use any of them. I tried a couple of them in the early days– years ago at this point, and to be honest with you, I'm not the target market for these things, and I’ll tell you why in a minute. So I’m not going to base this off of my personal experiences. What I did do is read a lot of reviews on the bigger ones, and I watched a lot of youtube videos of people testing them out, sharing their thoughts, and for those of you who say I wish you would put out an episode every week…you need to know that I watched almost 8 hours of reviews for these episodes–and that’s on 1.5 speed, so yeah, every week, just isn’t going to happen. So that’s that.
Anyway, I read the overviews on the app’s websites to understand what they’re supposed to do, read reviews NOT on their site to see what people really thought, and watched videos to see them in action–and now I feel qualified to share my thoughts.
Most of them have some features in common like closet inventory–where you take pics of all the clothes you own, the apps stores the items, and then it generates outfit ideas based on what you have.
Some offer body shape and or color analysis, some track how often you’re wearing your clothes and give cost per wear analysis, some offer shopping suggestions–there’s a whole host of things they claim to do.
Most of them though start with closet inventory as the basis, and for me as a user, this is where they fall apart. Its not because I’m a wardrobe stylist and I know how to put outfits together, and I rarely need ideas of what to wear–those things might be true, but the real reason I’m not the target market for these apps is that the process of taking photos of everything I own is just daunting. My ADHD brain got about 30% of my closet done, and then started doing something else, and I just didn’t go back to it. So if you need your entire closet photographed and inventoried to be able to use it, and you struggle to finish a project like this, the rest is kind of a moot point.
That was kind of a common criticism across the board–that they take a lot of work to set up, sort of defeating the time saving aspect in the beginning, but if you’re someone who doesn’t have issues finishing things, or you have a small wardrobe and it wouldn’t take a ton of time, or you’re playing the long game, thats not a problem. They’re just not quite as plug and play as maybe we’d like.
Another thing most of them do is create outfit combinations based on what you already own, or what you own and some additional shopping suggestions. This seemed to be the feature people found most beneficial, across all the apps. But I found something kind of interesting when watching the reviews on youtube. One thing I did was to make sure I wasn’t only watching style creators reviewing these apps–i wanted people who didn’t have a strong style foundation too. Because I noticed the style creators would take the idea, make a few tweaks, and be like, “I love this outfit–what a great idea”. Its kind of like when you read a recipe review, and someone gives it 5 stars, but shares all the things they did to change it–and you think–you just gave your own recipe a 5 star rating, because you didn’t make the same thing as the original. If the app suggests jeans, a blouse, and a blazer, and you end up in a maxi skirt, t-shirt, and cardigan, I don’t know that the app did that much for you. I mean, I guess it suggested clothes, and you wore clothes, so there’s that, but I’m pretty sure that without the app, they wouldn’t have left the house naked.
From the non-style creator side, I noticed a couple of things. First, there was a lot of “I would have never thought to put this together”, and as a stylist, and a capsule guide creator–those are words that fill me with joy. Helping people see things-especially things they already own–in a new way, to me, is a huge win, so I think that’s a wonderful use of these apps. Anything that helps you get more mileage and more style out of your current wardrobe is great.
ON the other hand, I saw a few instances where the outfit inspo should have worked in theory, but didn’t translate to real life. For example, there was a woman layering a t-shirt under a cardigan sweater, which seems pretty straight forward, right? But the tshirt was kind of cropped and boxy, and had wide, lower cut armholes, and the cardigan was not a super oversized fit, so the cardigan arms made the tshirt sit weird, and i wanted to reach through my screen and just pull her shirt down and adjust it, or better yet, swap it out for a tee that was a better layering piece. Just because a t-shirt SHOULD go under a cardigan, it doesn’t mean that every t-shirt works with every cardigan. Now, I don’t know if she eventually realized what was off about her outfit, or if anything was off about her outfit. In the video, she seemed to be going with it, but from my experience, I know there are people who will do, or wear, ANYTHING you tell them to do or wear. Especially people who are worried about doing style right. They’ll take what the authority says at face value, because they’re the authority, so they must be right.
This is actually a HUGE problem, and a theme that’s going to come up again next episode. A question I see come up over and over at Style Coaching, or just in our Community is “does this work”--do these pants work with these shoes? Does this top work with this skirt? And here’s the thing–these are people showing us photos of the outfit in question. They’re looking at the actual items on their bodies and still wondering, it’s not just theoretical. What these apps can do is give you ideas, give you suggestions…what they can’t do is guarantee they’ll work. There are so many reasons things don’t go together in real life–sometimes the colors are a little off, sometimes the fabrics don’t play well together, the proportions can be a mismatch–I could go on and on–and unless you know how to not only identify, but actually fix those things, the app is not going to improve your style, or make it easier.
Another feature of some of the AI style apps that got good reviews was wardrobe usage, and cost-per-wear tracking. Meaning, at the end of the month, or the year, it tells you, you wore 50% of the items in your closet, or whatever. One of the apps has you enter the purchase price of the item when you upload the photo, and when you log that item in your daily outfit tracker, it logs the wear count, and calculates the cost per wear, which, over time decreases as you wear that piece more often. We have a couple of members who use these apps, and they really like these tracking features.
If your mind works that way, I think that’s great. But I have a couple of questions about this–first, how do you take into account how many times you’ve worn it already? A five-year-old sweater you’ve already worn 50 times inherently has a lower cost per wear than something new you put into your wardrobe. But my bigger question is, what are you really learning from the data? Which pieces of your wardrobe you wear most often? I can stand in my closet and tell you that in 5 seconds, and I bet you could too. Another question is, what are you doing with that data? How is that knowledge helping you make better wardrobe decisions? If you discover that you’re only wearing 30% of your closet, like most women, cool. Then what? Are you intentionally changing your strategy for getting dressed to increase that number? Are you asking yourself WHY you’re only wearing 30% of your wardrobe? If a woman came to me, and said, my phone told me I’m only wearing a third of my wardrobe, I’d say, it sounds like you don’t WANT to wear the majority of your clothes, let’s figure out why. Is it that your closet doesn’t reflect the life you really live? Do your clothes not fit or flatter you? Are you missing key pieces, creating closet gridlock? Do you just not like your clothes? The information is only valuable if you DO something with it. I think there are some cases where this could be helpful–like if you challenge yourself to wear everything in your wardrobe, and you use this to track it. But if you don’t do anything with those numbers, it's just nice to know info, and my concern is that opportunities for deeper learning, and understanding get missed because we think we really think we’ve done something.
It’s the same with cost per wear tracking. In my opinion, the concept of cost-per-wear is really good when it comes to helping you make better buying decisions. You know, you buy a $20 pair of shoes that hurt your feet, wear them twice, that’s $10 per wear. You buy a $200 pair of shoes that are super comfortable, and you wear them 100 times, you’re at $2 per wear. That’s clearly the better purchase, right? The point of cost per wear is to help you make better buying decisions, and I’m all about that, so great. But what numbers can’t take into account is how something makes you feel. Let’s say I have a pair of black pants in my wardrobe, and a pair of bright pink pants. Common sense tells me the neutral, versatile black pants are probably getting worn more often, so even if they started out priced the same as the pink pants, the cost per wear is going to be lower. If I’m using that information to guide buying decisions, my takeaway might be, don’t buy fun pants. But what if those pink pants make me feel like a million bucks? What if every time I wear them, I get compliments and feel like the best, most stylish version of myself? Which is the better deal then? There’s an X factor that simple math can’t account for. This is another case where I don’t need an app to tell me which items in my closet were good investments, and which weren’t, and again, I bet you don’t either. At a higher level, the concept of cost per wear is wonderful and helpful, but I worry that getting super granular with it could discourage trying new things, or investing more in pieces you just love–and those are things that are really important to personal style too.
The last feature of AI style apps that I want to briefly touch on is those that offer body shape and color analysis. In theory, this could be a game-changer. These are two of the things women struggle with the most when it comes to style–and if there was an easy, inexpensive, accessible solution, it could be incredible. But you know it’s not that simple.
We’re going to go deep into my issues with this one in the next episode, and I don’t want to be redundant, so I am going to leave you hanging, but what I will say for now is that the reviews across the board–on websites, in youtube videos, on social media all say that accuracy is a mixed bag, and we’re going to talk about why that’s a big problem in our next episode, so hold that thought, and for now let’s recap my thoughts on style AI apps.
Please remember that this is as of Spring 2026. If you’re listening in Fall 2026 or beyond, first off, hello future lady–I hope it’s nice where you are. I’m sure these apps have evolved since the time of the recording, and now they probably send a drone to your house to pick out your outfits, and steam them and hem your pants. My thoughts are based on today.
In the pro column, we’ve got closet management, tracking and data, outfit ideas, and people appear to have fun with them, which counts for a lot. Style should be fun. If it’s not, you’re doing it wrong.
In the con column, there’s missing context, variable accuracy, and kind of a “so what?” when it comes to the data you get.
My overall opinion is this–they can be a fun, helpful tool, when used correctly. Can they make style easier? Yeah, maybe–I can see the outfit suggestions being really helpful for a lot of women.
But, can they actually improve your style long term? Probably not. Giving you outfit ideas each day makes it easier to get dressed in the moment, but it can’t replace the skills you learn from picking a top out of your closet and challenging yourself to make 5 outfits with it. That builds your lifelong style skills–which is what I, and this show, are all about. Not the quick fix of looking cute in one outfit one day, but rather the lifelong skills of being able to figure out how to make better buying decisions, and how to put together outfits that work, and how to fix them when they don’t.
In the end, I think it all depends on what your goals are and how you’re using the tools. As a support and a companion to the actual skills and knowledge you have? Yes. As a replacement for those skills and knowledge? No, they’re not ready to do that.
One thought I kept coming back to when putting this episode together is the concept of easy, cheap and good. This might be something you’ve heard me talk about before, but if you haven’t, here’s a quick recap. When it comes to pretty much anything–like planning a party, or going on vacation, or in this case, ai style apps, we want things to be easy, cheap, and good. The reality, though, is that you can only have 2 of the three, and the one you don’t choose is what you won’t get. For example, you can hire a party planner to throw an amazing event–you don’t have to lift a finger from planning to clean up. That is easy, and good–but you know that’s not cheap. You can cook all the food yourself, and do all the prepwork and cleanup, and handmake all the decorations to save money, and you’ll end up with something that is good and cheap, but definitely not easy. Finally, you can buy a pack of balloons at the dollar store, use plain paper plates and napkins you stole from McDonald's, and serve tap water and ramen. It's easy, it’s cheap... probably not that good.
The thing is, there’s no right or wrong answer here–it’s just priorities–the value is in knowing what you want, and what you’re going to have to give up to get it. Inherently, these AI style apps are meant to be easy and cheap–so what are they not going to be? I’ll let you fill in the blank.
Your homework for this episode is to check the apps out. I don’t want your takeaway from this episode to be “Jen say AI style app bad. Only Jennifer good”. That’s not the case at all. I just want you to be able to think critically about them, and know what their strengths and limitations are, so you can decide if they’ll actually make your style easier or better.
Here are 3 questions to think about as you’re checking them out.
First and foremost, are you willing to do the setup? Be honest with yourself–if you’re like me, and you won’t follow through, it won’t work. It’s that simple. Along with that though, will you use it consistently? Because spending all that time photographing uploading is a waste if you’re not going to try the outfits it gives you, or you’re not going to consistently log every outfit you wear.
#2-Do you want outfit ideas, or do you want to understand what actually works together? If I could get my act together to input my wardrobe, more outfit ideas might be fun–it could encourage me to think about my wardrobe in new ways, and that’s never a bad thing. But these apps depend on you already knowing if an outfit works or doesn’t, and why. If that’s the part you struggle with, these apps aren’t going to teach you that. They make outfits based on what should theoretically work, but they depend on you to get your looks over the finish line.
Something to consider if you say you want outfit ideas is this–do you actually like most of your wardrobe? Because if you don’t have ingredients to make outfits you’ll like, the app isn't going to magically change that. Like, if your wardrobe is heavy on basics, and muted neutral colors, and simple jewelry, and you’re hoping the app will help you make exciting, bold outfits, it won’t. It can’t. You have to find an app that’s more focused on shopping than remixing your current wardrobe. That’s not a bad thing, it’s just about knowing what your goals are, what you’re working with…and choosing the tool that will help you get there.
Final question: If you’re choosing an app based on its amazing data collection abilities, ask yourself how you’ll realistically and strategically use that information. How will knowing you only wear 20% of your wardrobe change your shopping and getting dressed habits? What will be different going forward, knowing the cost per wear of your items? I love data as much as the next nerd but if you’re spending all the time it takes to set up your closet, track every single thing you wear every day JUST so you can know you wear your jeans more than you wear your sequined midi skirt…is that time well spent? I don’t know you, but I’d be willing to bet you wear your jeans more often. Call it a hunch.
I think it might be fun to estimate how much of your wardrobe you think you wear, and then track it—how off were you? Most of us probably wear a whole lot less than we think we do. But there again, how much effort would it take to test and prove my hypothesis. More than I’m willing to spend, I’ll tell you that.
Have fun playing with these apps over the next couple of weeks. –I’d love to hear your thoughts–do you use them? Do you like them? How are they making style easier or better? Follow me on Instagram at @everydaystylewithjen and let me know.
Like I said, we’re going to pick up this conversation in our next episode, talking about where my experience with AI and style started–with good old ChatGPT. We’re going to dig into how tools like this do when it comes to making style easier and better. Are they better than the apps? Worse? I have so many thoughts on the subject–so very many.
That’s it for this episode of the Everyday Style School. Thank you for spending time with me today. If you’re ready for actual easier, better style, come take my free workshop Style Made Simple, where you’ll discover why style has felt so hard–and how to make it easy for life. You can sign up at freestyleclass.com, or through the link in the shownotes.
I’ll see you next time–and until then, stay stylish!