Hello hello! Hope you all have been well. Each day here is more and more humid while my hay fever is in full blaze, which means summer is fast approaching and June is right around the corner! What else does that mean?? Time to get those gay/bi/trans/lesbian/ace/demisexual/queer outfits ready!!

This is the first time in a long time where I’m planning ahead for pride. Mostly because I bought tickets to an event, but also because it’s World Pride in DC, and in these dark times I’m raring to go, and am ready to serve! That being said, the last time I attended a music festival was… ten years ago? So I’m in need some help… and who better to ask in 2025 than artificial intelligence? Have you heard that Chat GPT is now going shopping? Woof, capitalism! But as long as it stays free to use to help me navigate professional settings, I’ll bite. Plus, I’m curious to see what sense of personal style ChatGPT has.
So here we go baddies *-.-*
I began with all my usual research on pinterest, tiktok, instagram, in order to wet the palette and see what’s out there. Since I’m attending a music festival that is also a pride event (I LOVE BEING QUEER) I wanted to know what styles are recognizable at both these days. While the woman in this photo is at neither of those places, I found it on pinterest, and it reeeaaaallllyyyyy peaked my interest:

First of all, incredible use of contrast with this casual mesh tank against the tailored skirt and loafers. Neutral tones with white unders and socks to bring it all together?? Chef’s kiss. Anyway, for Pride, I want to look like this gal, but more sporty, less loafers, as we will be dancing on a field that is probably made of dirt and grass.
One moment, still hyper-fixating on this top: maybe a year or two back, I saw some brand online label a mesh tank like this a “Kiki top.” I clocked it and thought it was fun and yes, pretty gay, but didn’t quite make the connection until today when I looked up the Let’s Have a Kiki music video.

So from here on out, we are always referring to mesh tank tops as Kiki tops. I love when things connect organically! And I love learning new words. You’re welcome for the queer lore.
Anyway, zooming back out to the whole outfit for this pride event. I quickly made a flexible list of other elements that are important to me:
- accessories, including hat! I hear a bucket hat calling my name…
- some kind of layer for when the sun goes down
- a bag, depending on if I choose shorts that are sturdy enough to hold my belongings
- sweat resistant (sorry no glitter for me), it’s going to be humid af in DC, if not raining
- comfy shoes
- i am a little boho natural babe too so a touch of that would be nice
- it’d be cute to have a secret rainbow somewhere, maybe on a fan!
Okay so now it’s time to consult ChatGPT!

This is a good start, because it feels very music festival oriented (environment is key when choosing an outfit) and vague but a perfect place to narrow it down from. Knowing I’m not gonna want to wear glitter in this heat, I asked for a combination of cool and boho styles. They proceeded to give me a bunch of flowy dresses, and one thing I’m not going to do is wear a dress to pride, so I asked for something else.

Lol this isn’t exactly my style either. At this point, they are feeling a little slow on the pick up but I push forward with my next demand from my artificial stylist: lose the boho, not really my vibe. Side note: Chat kept responding with an “Absolutely!” at the beginning of each response, which felt sort of glitchy, because I know they have other affirming acknowledgements in their vocabulary.

A total shift, I liked these new suggestions. We were starting to get somewhere! I don’t really want to carry a bag, so I would be need of large pockets, and cargo shorts are the perfect suggestion.

Up until this point I was really just asking clarifying questions, trying to find silhouettes and ~vibes~ for this fun event fit. But now with an actual suggestion I like, let me investigate further, click click…ChatGPT!! Half of the links didn’t work! With the exception of Los Angeles Apparel, most of them are either shipping from Dubai (bro), or lead me to an unfound page.

I did ask more questions about bucket hats and ChatGPT sent me some functioning links to some homeware stores that happen to sell hats as well. I asked about jewelry and got some Etsy links that no longer exist. 50% is still a failing grade. I guess I was expecting more Urban Outfitters types of references. Not one Target link in sight! Cool, I suppose. But as someone who doesn’t love shopping for clothes online as it is, these links felt so random and glitchy, I wasn’t inclined to trust them.
Disappointed, you could say, because I want ChatBestie to thrive. A couple months ago, I got over the fear of asking AI to help me find relatively simple answers to things like “How to start a business,” and I really like the easy and positive interaction I get with ChatGPT. I also realized you can’t rely on only AI, because paperwork is old and convoluted. In this circumstance, I think I’m going to blow my whole budget on a kiki top anyway and just wear some colorful athletic shorts I already own, so no harm no foul with Chat being a little slow. But if I were on a mission to buy, buy, buy! This would not cut it, babes. I thought this was cutting edge, and it’s sharing links that are nonfunctioning? Too bad, but I suppose it’s nice to think that ChatGPT hasn’t become merely a tool of capitalism just yet. It’s weird to think that I’m a better tool of capitalism than this robot. But maybe that’s the beauty of OpenAI, of something that may not be cutting edge, but is free for everyone to use and learn from.

So through this process we learned that ChatGPT is an ally – I feel appreciated and not judged for my gender-non conforming fashion choices. Thank you, Chat! But a terrible stylist, because where are the clothes? Broken links aren’t helpful at all, and rather frustrating. Is ChatBestie a better therapist than a stylist? Whatever judgment calls one wishes to make about ChatGPT, I have found it to be a great starting point to a conversation, a wonderful backboard to bounce ideas off of.
Okay, that’s it for a few weeks! I’ll be back in June to show off the fit and for more talk unless my circumstances demand otherwise. In the meantime, stay safe, be vigilant, and I wish you the best of luck in finding your peace. I know I need it.
xoxo Carson
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