The irony of writing an article about how ChatGPT would completely change my life if only I let it pick out my outfits each day is that I spend way too much time deciding what to wear every morning. Way. Too.
Freaking. Much. Time.
Ever since I started my career as a fashion blogger three years ago, getting dressed each morning has been a struggle. I live in fear of repeating items of clothing too frequently or wearing outfits that aren’t exciting enough to wear in public.
Sometimes I spend 20 minutes holding up a single t-shirt, contemplating if wearing it would make me look like a toddler refused to change out of their overalls or a trendy feminist embracing clichés.
When my friend Sarah dropped by one afternoon last month and saw me frustratedly dancing around my closet wearing three different shirts at once, she laughed. “Why don’t you ask ChatGPT what to wear?” she suggested. “Bet it can’t do better than whatever stressball routine you’re doing in here right now.” Obviously, asking a robot to pick out my entire wardrobe was not going to happen.
Or so I thought… The thought stuck with me, though. What if I really did ask ChatGPT to pick out my outfits for a month?
Would I end up dressing like a crazy person? Would my style improve dramatically? Would refusing to make these decisions myself break me as a person?
I knew this was content the second Sarah said it. It was quirky. It was weird.
It was the type of commitment to artificial intelligence that would either win me millions of followers or prove to the entire internet that I’ve lost my mind. So naturally, I decided to do it. I took inventory of my entire closet that weekend.
Pretty much everything I owned ended up photographed and logged onto a spreadsheet so ChatGPT would be able to select from every piece of clothing I owned. This was when I realised how unhealthy my shopping habits had become. I own so many clothes I never wear!
Whole sections of my closet are dedicated to “things I thought looked nice on the display models but have no idea how to style with my actual body.” Estimate: thirty-seven percent of my wardrobe. After probably too-long deliberating over what algorithms would work best, I came up with this: Morning of Day 1: ChatGPT suggests denim trousers and a jumper. Pfft, how original.
Day 1: After realising that super basic looked insanely good on me, I wore the jeans and jumper with some over-the-knee boots and colourful jewellery. I spend too much time every morning worrying about what to wear. Would denim trousers and a jumper really BREAK me?
Well, colour me shocked when not one single thing happened. The AI in my phone suggested perfectly reasonable outfit combinations for the entire week. Skinny jeans, blouse, cute cardigan.
Bootcut jeans, jumper, white button-up. Things I might have worn if I had just trusted myself to get dressed on the first. Then it happened.
Day eight, ChatGPT suggested I wear “that cute band t-shirt you got from the thrift store two years ago with your structured blazer and wide-leg trousers.” Oh god. What have I got myself into? The shirt in question was from some eighties glam metal band I didn’t recognise, faded from too many washes and softer than a cloud.
I’d bought it years ago and originally intended to save it for weekends, but it ended up stuffed into my closet for basically ever. Along with wide-leg trousers. Combine that with the tailored blazer I’d chosen and my outfit sounded pretty damn horrific.
Boardroom fabric mixed with dive-bar fabric? Who does that?! Me apparently.
But ChatGPT was sure I’d look great, so great I was, tossing that whole combo on without a second thought. And you know what? It was amazing!
The blazer toned down my ratty old t-shirt and the t-shirt softened my blazer. I felt awesome – got more compliments that day than I had in months. This became a trend.
Blazer + t-shirt didn’t normally go together in my brain, but ChatGPT kept picking them as outfits, and once I bit the bullet and tried it, I loved it. As did literally everyone else when ChatGPT somehow conceived the idea for me to wear my yellow midi skirt with a black turtle neck and ankle boots. Nothing about that sentence should work.
It should sound horrible. But together it was magical. That’s when it hit me.
How many rules about what I can and can’t wear had I made up in my own head? This fabric isn’t office-appropriate. That neckline’s too décolleté.
I couldn’t wear yellow because no one would understand my fashion sense. I don’t have legs for boots. So restricting.
None of that was true. Yes, I worked in an office, but my boss had always encouraged me to dress with personality. Yes, I wore yellow, all the time – it was my favourite colour.
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And my legs were fine! I was writing excuses left and right to keep myself trapped in my angsty teen years. Day fifteen rolls around and ChatGPT really lays into me with this one.
Cute printed maxi dress paired with your denim jacket and… oh hell no. BOOTS. With a dress.
I legit refused to leave my house thinking about that look. It was chaos. It wastrying way too hard.
It was me. But hey, I told myself to wear it. So wear it I did.
And you know what? Three separate people stopped me to ask about that dress. A street-style photographer actually asked if he could take my photo.
I felt absolutely mortified…and amazing at the same time. As weird as it sounds, I started to view getting dressed in a whole new way once I let go and wore whatever ChatGPT spat out at me. I stopped overanalyzing my outfits as much.
Once you’ve rocked silver lamé trousers to the grocery store, normal clothes don’t seem so daunting. I also learned to stop ignoring so much of my closet. There were a bunch of items I’d purchased for “special occasions” or “days I was feeling extra cute” but never actually worn.
The silky blouse that was “too fancy” to wear to run errands. The cute earrings that I was “saving” for some unknown event. The vintage leather jacket I swore would make me look “too cool” to be a marketing associate who binge-watched reality TV.
ChatGPT didn’t care about any of that nonsense. It just read my closet as a list of articles of clothing and mixed and matched however the algorithm worked. ChatGPT didn’t know (or care) that I felt self-conscious about the sleeves being too dang short to cover my arms last summer when I bought that top.
Or that I was terrified of being overdressed whenever I considered that silk blouse as an option. Or that I thought people would criticise me if I wore that leather jacket as everyday apparel. By the third week, I was actually excited to see what ChatGPT would come up with for me that day.
Some days were absolute bombs; I still cringe thinking about the crop top and high-waisted leggings that made me look like I was dressed for senior year of high school in 2003. Or the day it made me wear white trousers when it was gonna rain…those are still in the wash. But most days I ended up with outfits I would have never tried, but ended up loving.
Hell, I even started taking pictures of what I wore each day at first for this article, and then because I was genuinely curious to see what ChatGPT came up with for me that day. I realised that the more weird combinations I wore, the more adventurous I got with my entire wardrobe. All of those “safe” outfits I reached for on days I didn’t have to think about what I was wearing were boring.
They didn’t say anything about who I am as a person or what I like. They were…safe. Plain.
Simple. Bland. I asked ChatGPT on the final day what it thought was the “best” outfit it could come up with from my closet.
Fully expecting some glam ensemble full of bizarre textures and patterns after a month of increasingly wild suggestions. It responded with skinny jeans, a white button-up, black blazer. Plain gold necklace.
Plain gold bracelet. Ugh. Basic bitch ChatGPT went right down to the core on me, didn’t it?
Reluctantly I got dressed in the “outfit of my life” and felt… great. Maybe it was coming from wearing metallic trousers to run errands and hiking boots with a pleated midi skirt for two whole weeks. Maybe I was overthinking it less since I let a robot tell me what to wear every morning.
But something about that classic outfit I would have rolled my eyes at a month prior felt different. It felt right. Sarah saw me wearing my computer’s idea of the best outfit humanly possible and chuckled. “That’s it?” She questioned. “ChatGPT only came up with that?” “It’s not bad,” I replied as we rocked back in our backyard chairs.
Sun setting. Photos of my month of crazy outfits all around us. “It’s fine,” Sarah responded. “You look fine.
Like you actually understand your style now, rather than trying to hide behind crazy prints and textures.” She’s not wrong, of course.
The majority of my fashion hangups were things I created myself.
Why I shouldn’t wear certain fabrics. Or boots with that shirt.
Or that goddamn dress to the grocery store. Truth is, sometimes you wear silver lamé trousers to pick up groceries and no one cares. Sometimes you pair a band t-shirt with tailored trousers and people praise your “creativity.” Sometimes the best outfit is jeans and a nice shirt and you don’t overthink every part of your body’s silhouette while getting dressed.
I’m still dressing myself these days, but man do I have a better time of it now. I wear that leather jacket twice a week. Tried mixing and matching pieces I loved but swore I couldn’t for years – and almost always loved the results.
And stopped standing in front of my closet each morning debating the meaning of life. Although I did have to draw the line at Sarah’s suggestion that I let TikTok pick out my skincare routine for a month. We simply cannot know every outcome of these life-changing experiments.
