Is there a tougher time of the year to dress than March in the US? It’s not really winter. It’s certainly not spring, and your sweaters, short sleeves, jeans, and shorts are all staring warily at each other. It’s a wonder I don’t spend every day in my PJs. What if AI could help us make the right choice?
While preparing for another day in the home office, I did my nightly next-day weather check. For this task, I invariably check in with Alexa. Amazon has yet to deliver the big AI, Alexa+, update to its popular digital assistant, but Alexa has long been an excellent weather person. So when I asked about the weather for the next day in my neighborhood, Alexa described the stereo-typical March conundrum: a low of 48 and a high of 58 with rain across all of it.
I froze, as one does, unsure if this was sweater sweater, t-shirt weather, layer weather, or something else. What if, I wondered, could AI help?
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Fashion, however, is a deeply personal thing, and I worried that generalized advice wouldn’t help me. What I wanted was for generative AI to look at my closet and, if not choose, at least help me pick out my outfit.
Since it now lives on my iPhone lock screen and I’d had some success with Gemini and game generation, I decided to start with Gemini Live running the Flash model 2.0 in my Ides of March fashion quest.
Here’s the voice prompt I used:
If I show you my closet, can you tell me what to wear tomorrow? The high is going to be 58° the lowest going to be 48 and it’s going to be rainy.
Gemini’s slightly disappointing response arrived quickly. “Unfortunately, I can’t see what’s in your closet yet.” Still, it did follow with a good bit of dress-wear advice:
“But with those temperatures, you’ll want to layer up for sure. A good base layer, like a long-sleeved t-shirt or a light sweater, is a must. On top of that, think about a jacket or coat that can keep you dry in the rain. You might also want to pack a scarf or gloves, just in case.”
I had neglected to mention that I might not leave the house, so the scarf and gloves made sense.
This was useful, but I expect multi-modal capabilities that can hear and see my needs, intentions, and choices and come up with the best results. Otherwise, why use AI in the first place?
Next, I tried Siri. I held down the Siri button on the side of my iPhone 16 Pro Max and repeated the prompt. The results were comically bad: Siri simply presented the next day’s weather range and offered zero sartorial guidance. Oh, Siri, when will you get that desperately needed upgrade?
Chatting clothes horse
Finally, I switched to ChatGPT 4o voice mode and asked virtually the same question. Unlike Gemini, ChatGPT was all too happy to comply:
Of course! Turn on your camera and show me your closet. I’ll help you pick something suitable for the weather.
I turned my camera, started scanning the contents with my iPhone, and asked, “What do you think?”
ChatGPT responded:
“It looks like you have some nice long-sleeve shirts and some jackets. Since it’s going to be cool and rainy, I’d suggest wearing a long-sleeve shirt with a light jacket or sweater. Pair that with some comfortable pants, and you’ll be good to go! Do you have a favorite sweater or jacket you want to use?
We went back and forth a bit like this. At one point, I told ChatGPT I didn’t want to wear a sweater (my own quiet protest against weather that I think should be warmer already), and it suggested a jacket instead.
Neither ChatGPT nor Gemini Live picked out a specific shirt and pair of pants, but I’m not sure my closet was arranged in a way that they could make out each piece of clothing. On the other hand, I was pleased that neither steered me toward a short sleeve or single layer. It’s like they were both looking out for my comfort.
AI for the Fashion Guy
To understand my fashion struggle, though, you should know something else about me: I’m color blind. Not 100%. I can see colors, but hues, shades, or colors that are too close, reds, browns, dark blues, and dark greens can all throw me. There was a time when I would have my wife check me before I walked out the door each morning: “Do I look OK? does this match?” She’d glance sideways, give the tiniest head shake, and I’d head back to the closet.
Could my AI fashion guides offer similar support?
The following morning, I grabbed the jeans and long-sleeve shirt I’d selected, opened Gemini, selected the “+” icon to add a photo, and then asked Gemini:
“Do you remember when we were talking yesterday about what to wear? Do these two pieces of clothing go together?”
Gemini cheerfully responded:
“Absolutely! It’s great to revisit this.
Yes, based on the image you’ve provided, the blue plaid shirt and the blue jeans definitely go together. Here’s why:
* Color Harmony: The blues in both pieces are complementary. The shirt has a mix of navy and lighter blues, while the jeans are a classic medium-wash blue. This creates a cohesive and visually appealing look.
* Casual Style: Both the shirt and jeans are inherently casual pieces. They work well together for a relaxed, everyday outfit.
* Versatility: The plaid shirt can be dressed up slightly with chinos or dress pants, or kept casual with jeans. Similarly, the jeans can be paired with a t-shirt, sweater, or even a blazer.
In short, this is a classic and stylish casual outfit combination!
Let me know if you’d like suggestions on how to accessorize this look or if you have any other clothing questions! 😊”
Plaid talk
It’s worth noting that when Gemini described my “blue plaid shirt,” I was somewhat surprised because I thought it was black. This happens a lot to me – darn color blindness– but at least I successfully created an ensemble with “a cohesive and visually appealing look.”
When I switched to ChatGPT 4o, it was equally excited to return to the sartorial topic and told me I could hold up my outfit choice or describe it.
I selected the camera button in the ChatGPT voice interface, took a snap, and immediately got a fashion review:
“Yes, I can see them. That plaid shirt and jeans look great together! It’s a casual and comfortable combination.”
ChatGPT did not comment on the shirt or jeans colors, but it seemed satisfied that I had properly matched my outfit.
This process was more than a few steps removed from a true AI fashion guru planted inside my closet who would know my wardrobe and the weather outside and then choose the perfect outfit for the day. Still, I was impressed, especially with ChatGPT 4o’s more seamless, multimodal fashion capabilities. It was ready to look in my closet, take it all in, and at least make some general recommendations.
Gemini Live was, with some gentle nudging, close behind and gave me more detailed feedback. So it’s ChatGPT by a fashionable nose, but Gemini is probably also ready for your runway walk.
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