I let ChatGPT pick my outfits for a week, here’s how it went

Is my new stylist an artificial intelligence chatbot?

Whether I’m having lunch with my brother or going to an important work event, my entire wardrobe somehow seems to end up on my bed when I’m getting dressed. I’m typically pretty creative when it comes to my fashion, but choosing the ‘perfect’ fit seems to be a daily hurdle for me that sometimes causes more stress than necessary. After wasting far too long and trying several fits on, I frequently end up reverting to an option I’ve worn several times before and call it a day.

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Could ChatGPT be the solution to my problems? To find out, I let the artificial intelligence chatbot plan my outfits for the week. Obviously. Sure I’m a little terrified of AI, but ever since I realised it can do so much more than draft emails and reword sentences, it’s been growing on me. So, I thought why not live out my Clueless dreams (cue the iconic scene of Cher swiping through her wardrobe) and let a robot plan my week in outfits? 

How does it work?

I opened ChatGPT and pretended it was my stylist. I provided it with a short brief outlining rough weather conditions, some pieces I owned and wanted to include in the week’s outfits, plus some fashion inspiration. I also asked for it in a table, cause I’m a visual gal who gets a kick from a good spreadsheet. 

For the first attempt, it was pretty good. I had most of the items listed in the table but had to give ChatGPT some feedback regarding items I don’t own. 

I was vibing the options ChatGPT picked out for me and thought I’d push the boundaries a little further. I asked it to select my accessories, hair and makeup for the full effect. 

With my final table fully populated, I was set for the week and ready to ‘have fun experimenting’ with my new looks thanks to ChatGPT. 

Monday

We kicked the week off strong. This outfit combined a bunch of my wardrobe staples. I always reach out for each of these individual pieces but have never actually styled them all together. Reflecting on the week, this had to be one of my highlights because, in my opinion, it struck the perfect balance between comfy and cool. Plus it’s versatile enough for a coffee meeting or wine with friends.

Tuesday

Another day, another slay. Tuesday was a strong but simple outfit that featured my beloved jeans. I wore my Superga sneakers that I planned on selling – but after wearing them for a day, I had a fresh wardrobe perspective. 

While I didn’t opt for the smoky eye (I thought it was a bit much for a Tuesday), I wore my hair natural in a half-up, half-down style, as ChatGPT suggested. Surprisingly, I got a couple of compliments on it. For accessories, I went with oversized sunnies that matched nicely with my amber bag. The accessory combo was probably my favourite and definitely something I’ll be adding to other outfits. 

Wednesday

Wednesday’s outfit felt perfect for autumn, with rich reds and vibrant purples. Wearing a red lip is usually something I reserve for the evening, but doing it during the day made me feel both over the top for a chill lunch catch-up and also like a complete baddie.

My friend Sohani also complimented my outfit – in particular, the purple bag which I rarely wear because I struggle to style it. A girl in the street also said she liked my pants so all in all, I say this was another win for ChatGPT. 

Thursday

This outfit was far more business-chic than my style tends to be, but I did feel like a boss. I wore this to a family birthday dinner, to which my dad (dressed in a tee and tracksuit) asked, “Why are you so dressed up?”. His partner complimented how I always look so fashionable.

Responding to both of their comments, I told them that ChatGPT is fully accountable for the outfit, so they can thank or blame the AI. They couldn’t quite wrap their head around the fact that a computer selected my outfits, but my brother was thoroughly amused and said he approved of my look. 

Friday

I realised I didn’t have a striped T-shirt, but do own a striped long-sleeve. I went with that and my corduroy pants. I initially tried this on with a blue denim jacket, but it looked ridiculous so opted for my beige one instead. For a neutral-coloured Canadian tuxedo, it’s not bad – but I don’t see myself reaching for this outfit again. This was the only outfit of the week I didn’t love, mainly because I think the styling blurs each garment into one. 

Saturday

I’ve worn this outfit before and I’ll be wearing it again. It’s simple, practical and cosy for a busy day. No complaints but just a side note – the cow-print bag was immensely impractical for a ‘running errands’ kind of a day. I ended up switching the bag for a tote. To be fair to ChatGPT, it didn’t know the bag was so small.

Sunday

ChatGPT finished the week off strong with an outfit I adore. I’ve worn this jeans and knit combo before but usually style it with sneakers. I loved the pointed heel as a slight elevation and also really liked pairing this outfit with a green bag, as I usually opt for a neutral black or white one. 

My day was made by the number of people who complimented this outfit (which also showed me my love language could be words of affirmation), so I owe a big thank you to ChatGPT for this outfit. 

Final thoughts

I really enjoyed not having to think about what to wear with a handy spreadsheet of outfits planned for me. It saved me a lot of time in the morning and I liked wearing options I don’t always reach for. My mornings were made simpler. I guess it did remove an element of creativity, however, all the individual garments were items I picked out so it still felt authentic to me. 

For the purpose of this experiment, I tried to stick as closely to the spreadsheet as possible. If I was to do it again, I think I’d use ChatGPT as a source of inspiration or guide to inform my styling. I definitely recommend giving this a try. I had a lot of fun doing it.

The process reminded me of wardrobe items I had forgotten about and also gave me new ways to style the pieces I struggle to wear. In the future, I see myself using prompts like, ‘Give me three looks to wear with my purple bag,’ or ‘Show me different ways I can style my beige denim jacket’. I’m curious to see what my new AI stylist has to suggest.

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