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I Love an Old Pair of Shoes I Purchased Years Ago. I Asked AI to Find Me a Similar Style

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Every woman can sympathize with this: You finally find jeans that make you feel good or a pair of heels that are both comfortable and stylish. And then, suddenly, it’s out of season or style, and there’s no way of finding that item again.

But some styles are timeless, and you’ll want to replace them when they’ve seen too many red wine spills or look a little weathered. The world of fashion moves faster than a Tinder swipe. Maybe artificial intelligence can help locate links to the original item sold elsewhere, or find a similar look. 

If AI can help find the best deals online, be used as a shopping assistant and even as a personal assistant, maybe it can help replace my gorgeous pair of heels that I can’t find anywhere.

With ChatGPT Search, I can upload a photo of my shoes, and it can search the internet for shopping links — like a Google reverse image search on steroids. There’s even specific AI shoe finder GPTs I could test out. 

(Disclosure: Ziff Davis, CNET’s parent company, in April filed a lawsuit against OpenAI, alleging it infringed Ziff Davis copyrights in training and operating its AI systems.)

Can ChatGPT magically find my favorite heels from a photo? 

The first step was to take a few photos of my beloved shoes from different angles, making sure to capture the brand name. I bought these shoes close to a decade ago, when I was still living in Australia.

I made sure to snap any defining features and codes, like a sticker that miraculously stayed on the sole through just about every terrain — grass, gravel, pavement and floorboards. 

Next, I opened up ChatGPT, logged in and uploaded four photos with this prompt: “This is an old pair of shoes I love. I want to replace them with either the same item or something similar. I’m a US size 8. The code on the sole is 8M/38½. Here are four photos of the heels.”

I made sure to select the Web Search button. 

ChatGPT / Screenshot by CNET

It gave me some identifying information in order to help me direct my own Google search, but I wanted it to do it for me. The point was to save time using AI.

ChatGPT / Screenshot by CNET

I responded with this prompt: “Can you search the internet for links to the exact item?” 

ChatGPT sourced a bunch of links with resale items and suggested I set up an alert using specific terms like “Lucky Brand Bertel black suede 8M.” 

While it didn’t provide the specific product link, I liked being able to sort through the resale pages to see similar styles too.

ChatGPT / Screenshot by CNET

Before I get deep into online thrifting mode on eBay, I asked ChatGPT to find five new styles that are similar, either from Lucky Brand or the others mentioned. 

This was fun! I learned that this product is a block-heel suede look, which is helpful to know for whenever I need to do my own searches: 

ChatGPT / Screenshot by CNET ChatGPT / Screenshot by CNET

My only critique so far is I’m not familiar with some of the stores ChatGPT provided links to. I wasn’t sure if it was just pulling from eBay and unknown websites because it was trying to find resale items. 

ChatGPT / Screenshot by CNET

So, I asked it to search sites that I’d usually buy shoes from, like DSW and Nordstrom. 

It came back with direct links to these websites with the search pre-populated as “Lucky Brand” or “women’s block heel sandals.” This saved me some searching time, taking me straight to things like this Nordstrom page:

ChatGPT / Screenshot by CNET

It suggested Marshalls/TJ Maxx, which I had forgotten in my previous prompt. I liked the recommendations it gave, such as a specific style for comfort or for a higher heel. It also provided tips on when these brands typically run sales. 

ChatGPT found me two heels I loved, but one was sold out:

ChatGPT / Screenshot by CNET

I found another two pairs of Lucky Brand finds from the links ChatGPT provided, only to discover they weren’t even my size, even though I included that in my prompt: 

ChatGPT / Screenshot by CNET

It was also interesting how the model didn’t add any links from the Lucky Brand site itself, only third-party sellers. Always back up your ChatGPT activity with your own manual research. 

AI chatbots can be a handy tool to get fashion advice, outfit recommendations, product comparisons and insights about your personal style. However, for online shopping, you’re better off going directly to the brands and sites you love. 

That’s the fun part anyway. 

I Love an Old Pair of Shoes I Purchased Years Ago. I Asked AI to Find Me a Similar Style
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