For many years I have defaults to wearing a t-shirt and jeans. It’s a classic combo, but it also can appear too casual depending on the context. Sometimes I need a decent outfit for an important appointment, like a date or a job interview or a holiday party. And some days, it just feels good to dress at a little higher level than normal.
I recently attended a short seminar on how to “build your brand”. It included many of the same concepts I learned in my Communications undergraduate studies, and was part of the reason why I even started this blog. But as I’ve been trying to figure what exactly my brand is, I’ve gone through many ideas. Obviously, this blog has a retro-futuristic, somewhat cyberpunk vibe, specifically because a major segment of the blog is focused on integrating technology in my life new ways. But I myself don’t dress in a cyberpunk style.
Now I have a tool that feels futuristic enough that I want to showcase using it to upgrade my wardrobe. ChatGPT has many incredible uses, and one that I recently discovered is that it is quite adept at understanding color matching and creating outfits.
Although I have some small understanding of style and color coordination, I’ve never really bothered. I think many guys don’t worry too much about what to wear, as long as they smell good and appear cleaned up. It’s often a matter of doing only what’s needed, especially in a world where there are so many opportunities to do other things. There’s also the unfortunate belief that “fashion” is a feminine ideal, and that guys should care less about their appearance because it’s somehow more manly.
I get that. I grew up with that line of thinking, and it still impacts what I buy and wear. But I really do want to be able to step it up and look good at any time for any reason. And if AI can take the load off my mind, then why not try it?
Use Case 1: My Current Options
AI is only as good as the prompts given to it. There are a few different ways that I’ve discovered to utilize its assistance. The first way is by feeding ChatGPT a prompt explaining what I have in my wardrobe, providing photos if possible. Then I ask it to take the articles I’ve shared with it to then generate an outfit that would look good together.
Here is an example. After I finished uploading the photos one at a time, I requested that it provide an outfit for Sunday worship. I also asked it to generate an image of the outfit showcasing a man wearing it and each piece on its own.
Here is the image it generated:
My slacks are a not quite that slim, but the overall aesthetic looks polished and classic. I tried on these pieces, changing out the tie for a blue paisley one, and here was the result:
If I had a full length mirror and a better phone camera, it would look better. But I’m pleased with the overall image.
Now that I’ve uploaded photos of every article of clothing I have in my wardrobe, I can ask ChatGPT any time for an outfit. I can plan the week ahead with little thought or stress. I can wear something knowing that it looks at least somewhat stylish. For example, I can tell it that I’m going out on Friday night to dinner on a first date, and it will provide a suggestion specifically for that night.
Something else I did was request that it assign an appropriate masculine given name to this ensemble. It dubbed this one “The Winston”.
After it generated the outfit and I uploaded the photo, I had ChatGPT analyze the fit on my body and consider what accessories might go with it. It suggested a silver wristwatch and silver cufflinks to match the blue and black combo. I unfortunately don’t own either of those things, but they are now on my list of things to buy.
Which brings me to the next use of AI.
Use Case 2: Potential Outfits
ChatGPT is great at generating potential outfits for pieces I don’t own yet. First, I asked it for additions to my wardrobe that could help me “up” my style a bit. It provided a few ideas, and then I told it “Let’s see some specific combos with the suggestions you made. With each suggestion, please provide names and descriptions of the types of articles presented, such as the type of shoe or the type of pants. Let’s start with the something smart and business casual.”
It provided three options for me to pick. The first one it called “Clean and Classic”, and listed the following:
Shirt: Light blue Oxford Button-Down Shirt – A staple in business casual, the Oxford shirt is slightly textured and more relaxed than a formal dress shirt, making it perfect for layering.
Pants: Slim-Fit Chinos in Navy – These provide a tailored look without feeling too formal, and navy is versatile enough to match various shirt colors.
Sweater: Lightweight V-Neck Sweater in Gray – Layered over the button-down, it adds warmth and style without feeling bulky or pretentious.
Shoes: Brown Leather Loafers – Loafers are comfortable and easy to slip on, offering a polished yet relaxed vibe that suits business casual perfectly.
I then asked it to generate an image of a man wearing the first outfit it suggested. Here is the result:
Then I asked ChatGPT to provide links to sites or pages that carry the specific pieces. I already have a pair of navy chinos and a brown belt, but I don’t have brown leather loafers or the tops. I specified that I didn’t want to break the bank. It has a little bit of difficulty finding links to exact listings, but it can point to search result pages and company sites. Here are the links:
https://www.target.com/s/mens+blue+oxford+shirt
https://oldnavy.gap.com/shop/mens-chinos
https://oldnavy.gap.com/shop/mens-lightweight-sweaters
https://www.nordstromrack.com/shop/men/shoes/comfort/loafers?filterByColor=brown
From there it was pretty easy to specify using each site’s filter what size and style I wanted. Within a few minutes, I had found eachof the items on the list using the links it provided.
https://oldnavy.gap.com/browse/product.do?pid=408049002&vid=1#pdp-page-content
For the last link, I searched through the results it provided and I couldn’t find quite the same shoe it had generated in the image. I tried searching the entire site and still couldn’t find it. I found many that were almost there, but which didn’t have the right color or the white bottoms or the laces. So I decided to ask for more links, and it gave me two more. The first pointed me to actual search results, and the second just sent me straight to the company website.
Unfortunately, after some searching on those sites, I had to resort to using Google’s reverse image search to find the exact shoe. The best option as from Calvin Klein and cost over $140 on eBay. Not exactly cheap, but for a nice pair of shoes it would be worth it.
My verdict is that ChatGPT is a helpful shopping assistant, but it has some limitations. I finally asked if it could provide direct links to listings on sites and it said it cannot do that. But at least it pointed me in the direction of inexpensive options for most of the pieces in the ensemble.
I’m still figuring out what “my brand” is, but I think part of it may be a desire to look sharp even in casual settings. And AI will help me get there.
-Zed