Choosing my outfit of the day has been a ritual I’ve practiced (and loved!) since I was in first grade. So temporarily “hiring” AI to be my personal stylist this last week was not only a little nerve-wrecking, but also somewhat challenging, since I’ve long grown accustomed to styling myself.
One of the major challenges I encountered this week was taking into account the fact that I’ve returned to my hometown of San Diego, California for the summer. It’s always a drastic change from attending university in New York, where I can stick to my typical outfit formula of my favorite miniskirts, faux fur boleros, and heels that would only make sense in the Big Apple. And after such a long period of time of running around the city to make it to class and attending various events left and right, all I want to do is hibernate when I come back to Cali. But with this challenge to tackle, I knew I couldn’t just lounge around in oversized crewnecks and denim shorts every day like I usually do.
So to put my mind at ease, I told myself this was simply me channeling my inner Cher Horowitz and allowing my closet (or in this case, ChatGPT) to help me curate an outfit that wasn’t a “mismatch.” Here’s how it went.
Day One
With the challenge of finding an outfit suitable for Memorial Day, I knew this would be a prime opportunity to put ChatGPT’s fashion sense to the test. Americana isn’t really my vibe, so finding something to wear to celebrate that still reflects my personal style has always been a challenge.
In my prompt, I described my love for all things cropped (boleros, miniskirts, crop tops) and how I often lean towards more traditionally feminine silhouettes. I was delighted when ChatGPT suggested I dress like a “Denim Dream Girl.” I had to swap out some of the clothing options since I didn’t have the exact same items, but to achieve the look it described, I opted for a red tank top, my favorite straight leg ZARA jeans, and a white faux fur bolero. It hasn’t quite hit peak summer weather here in Cali yet, so I was happy to wear the bolero — it’s not only one of my favorite pieces, but it’s also something that makes me feel the most me. I still adhered to the patriotic dress code, but I did it on my terms.
Day Two
Recently, I’ve been obsessed with an outfit formula Bella Hadid has perfected: a scooped top and classic denim. And with plans of scouring my local thrift stores, I knew this look had to be a good one. ChatGPT suggested I wear either a tube top or a light pink scooped tank, so I went with the latter. I wanted to wear a denim skirt like it prompted, but since I don’t have one, I chose a pair of medium wash, ultra-baggy jeans. It also suggested I wear a belt, and my black one was the perfect complement to my black Kate Spade shoulder bag.
Day Three
This day was a little lower stakes, since I planned on spending it doing work around the house. However, I still wanted to look cute while doing it. ChatGPT helped me look beyond my crewneck and shorts combo, and suggested I wear a cute loungewear-esque dress with a lightweight cardigan. Who knew doing chores could look so good?
Day Four
To revisit my thrifting day two days prior, I’m pleased to share that I was successful. I purchased this pink bubble hem top that I was excited to ask ChatGPT to style for me. And to my surprise, it encouraged me to outfit-repeat! To be fair, I was very specific with my fashion habits in my initial request. While I told it things like how my style is best described as “refined femininity,” I also expressed some of my outfit styling habits. I shared my love for balancing strict silhouettes like corsets and cropped, tailored jackets with lightweight skirts and flowy dresses, and I also shared how I’m not afraid to outfit-repeat, or at least change a smaller detail like the jewelry I wear or how I do my hair. So like I did on my thrift day, I styled my bubble hem top with a pair of baggy jeans, sneakers, and the same belt. Now I know why it’s one of Bella Hadid’s favorite outfit formulas.
Day Five
Day five was so much warmer compared to the rest of the week, so I knew I wanted to lean into the colorful Cali summer vibes I’ve adored all my life. ChatGPT suggested I go for an “Off Duty Mermaid” look, and style a pink tube top with one of my long, flowy skirts. In terms of accessories, I opted for a necklace that features a shell pendant, some pearl barrettes, and lots and lots of gold bracelets. It was probably one of my best summer looks to date!
If there’s anything I’ve learned from asking ChatGPT to help style me, it’s that fashion should be fun, even on the laziest of days when I’m just lounging around the house. Getting dressed doesn’t always have to mean going somewhere; sometimes it’s about showing up for yourself in a way that feels playful, personal, and a little unexpected. I also found it comforting (and kind of refreshing) that even ChatGPT champions the art of the outfit-repeat. Because let’s be honest, some pieces deserve more than one spotlight moment.
As someone who can easily get lost in the endless scroll of Pinterest mood boards, having a styling session with ChatGPT helped me cut through the noise. It kept me focused on my actual wardrobe and inspired me to wear things I might’ve otherwise overlooked, or thought were “too much” for everyday life. Instead of reaching for the same go-to pieces, I was nudged to rethink my basics and experiment with different combinations — all while staying true to my own aesthetic. Turns out, a little digital styling support goes a long way in helping you rediscover the fun hiding in your own closet.