I am terrified of using artificial intelligence. I don’t know if it’s because of professors’ constant warnings, or the many socially dangerous ramifications of its use. Either way, I have a genuine fear of getting accustomed to life with AI. But recently, I’ve been wanting to try things that I wouldn’t typically try — which is why I decided to ask the elusive, all-knowing entity of ChatGPT to choose my outfits.

I began with a simple question: “Hi ChatGPT! Can you help me pick out outfits?” 

ChatGPT responded: 

Hey! Absolutely, I’d love to help you pick out outfits. Just let me know a few things:

1. 1. What’s the occasion? (Casual day out, work, date, party, etc.)
   2. What’s the weather like?
   3. Any specific pieces you want to include? (Like a certain pair of jeans, shoes, or accessories.)
   4. What’s your general style vibe? (Trendy, minimal, edgy, preppy, boho, etc.)
   5. Do you want me to build full outfits or just give you ideas for tops, bottoms, and so on?
   6. Give me the deets and we’ll build some killer looks together!

I was surprised by the amount of detail it asked for and then provided detailed prompts for each of my desired outfits. 

Outfit 1

“My outfit today is for a casual day with friends, walking around SoHo and hanging out in Washington Square Park. I want something trendy, yet comfortable — it would be great if it included either my low-waisted baggy jeans or combat boots. The weather is springtime.”

The enthusiasm I received was far from the mechanical response that I expected: “Okayyyy I see you — that’s a vibe. Spring in SoHo and Washington Square? We need something that looks effortlessly cool, but still lets you chill comfortably while you’re out and about.” 

What impressed me most were the creative, quirkily-titled options that ChatGPT cooked up:

Casual Cool-Girl Fit (Baggy Jeans + Combat Boots Edition)

• • Top:
    • Fitted baby tee or ribbed tank in a soft color (white, heather gray, muted lavender)
    • OR go bold with a graphic tee — maybe something vintage-inspired or band tee style
  • Outer Layer:
    • Cropped bomber jacket, light utility jacket, or even a slouchy cardigan if it’s warmer
    • If you want some contrast: a feminine layer like a light cardigan or mesh long sleeve under the tee = chef’s kiss
  • Jeans: Your low-waisted baggy jeans, slightly cuffed at the bottom to show off the boots
  • Boots: Combat boots (black, chunky — they anchor the whole look and give that edge)
  • Accessories:
    • Belt (optional — a little flash of hardware looks intentional and trendy)
    • Tiny silver or mixed-metal hoops, or layered chains
    • A casual shoulder bag, canvas tote, or even a mini backpack
    • Sunglasses for that ‘NYC girl on the move’ effect

The pieces recommended all have a similar vibe, and likely are pieces that you already have some variation of in your closet. Based on the recommendations, I chose a beige utility jacket, my old graphic t-shirt from third grade, low-rise baggy blue jeans and leather combat boots. I paired these with tiny sunglasses and carried a small leather shoulder bag. This is surely an outfit I have worn before — ChatGPT didn’t necessarily teach me anything new — but it was nevertheless casual, easy to walk in and comfortable to wear the whole day. 

Outfit 2

“My outfit today is for a study date at a coffee shop and then going to a bookstore. I want something flirty and cute while not looking like I’m trying too hard. It would be great if this outfit included either a denim miniskirt or a leather jacket. The weather is springtime.”

Just like the previous response, the ever-sassy ChatGPT did not disappoint with its introduction: 

Ugh YES — study date + bookstore in the spring? That’s such a dreamy vibe. You want to look effortlessly flirty, like ‘Oh this? I just threw it on’ energy, while still giving main character. Let’s build a look around both the denim mini-skirt and the leather jacket — we’ll make them work together in the cutest way:

Flirty Coffee Shop Date Fit (with denim mini + leather jacket)
Think soft meets edgy, like Meg Ryan x modern Pinterest girl

• • Top: Fitted ribbed knit or lace-trim cami in a light shade (white, blush, pale blue — soft colors give a gentle vibe)
  • Skirt: Denim mini (medium wash looks great for spring; bonus if it has a little raw hem or button detail)
  • Jacket: Cropped or slightly oversized leather jacket (black or brown — both work depending on the rest of your palette)
  • Shoes:
    • Ballet flats or Mary Janes for a feminine touch
    • OR classic sneakers like Converse or platform Vans for cool-girl comfort
  • Accessories:
    • Small shoulder bag or a cute tote with a book sticking out 
    • Delicate gold or pearl jewelry — think subtle, not statement
    • Optional: Sheer tights if it’s breezy, and a soft headband or clip to finish it off

If you want to swap the cami for a button-up shirt half-tucked or a simple graphic baby tee, that also works and adds to the ‘I’m not trying too hard but I still look amazing’ aesthetic.

Following ChatGPT’s suggestion, I wore my low-rise dark-wash denim miniskirt, a long-sleeve ribbed button-up, a black leather jacket, sheer black tights and leather Camper sneakers. I accessorized the outfit with my small leather shoulder bag and tied a scrap strip of flannel fabric as a headband. Needless to say, ChatGPT did well — I ran into some of my friends when wearing this outfit who confirmed the effortlessly cute vibe I wanted.

Ultimately, these AI-generated outfits are objectively good. By feeding the program with clothing pieces, it was able to pair them with appropriate garments and accessories. Though the outfits are rather basic, this was expected. At its most basic level, ChatGPT synthesizes information from across the web, which in this case, meant borrowing heavily from pre-existing fashion media. But even as someone who usually avoids using AI at all costs, this was honestly a fun experiment. I would urge others to try it at least once, especially if you’re struggling to choose an outfit for the day. While you might not be satisfied with ChatGPT’s unoriginal suggestion, you’ll still get a laugh out of its sassy tone. 

Contact Sreya Nair at [email protected].