4 Pride Outfits: Rocking Your Colors, Flying Your Flag
Alright, you clicked, so as far as Pride Outfits are concerned, I’m gonna give it to you straight. Which, to be fair, is the only way I’m actually qualified to give it to you. If I were gay, I’d try to give it to you gay. If you were ace, I wouldn’t give it to you at all… respectfully, of course.
Back in the day I was in the shadow cast of Rocky Horror Picture Show. I even ran the damn thing for a while. Played every single character. EVERY character. Some of the best nights of my life. Weird part? Anytime “Time Warp” comes on there’s like a 35% chance I go catatonic… probably nothing.
The gay community was never this mysterious “other” to me. It was just another group of guys. Okay, sure, they usually dressed sharper than me and occasionally turned the volume up to eleven. But if you needed a wingman? Brother, they delivered. Honestly, I owe a chunk of my early sexual education to nights out with my gay friends. That sentence didn’t come out right, but we’re rolling with it.
This was circa late 1996 and so forth for years. I can remember the style of the 90s so much, which I mention here!
Anyway, a Pride Fest is hitting Orlando soon, and I started thinking about Pride Outfits. Everyone pictures the rainbow, but that’s only the tip of the iceberg. Each flag has its own vibe, its own look. And it got me wondering… what would it feel like to wear the flag? To throw an outfit together that actually channels the colors and the spirit? So let’s play around a little. Let’s see what it looks like when fashion flies the damn flag.
How do you make Pride outfits inspired by Pride flags?
Pride flags weren’t designed with fashion week in mind, but most of them can work across outfits if you play with color. Pride Fest is different. That’s when it’s about repping yourself, not blending in. Some flags vibe perfectly. Others… let’s just say rainbows don’t always hit unless you want full candy-store chic.
So if you have pieces like sports coats, T-shirts, vests, Hell, maybe some awesome socks! Try to match your flag and see if it’s fabulous. If it’s smiles for miles, then work it anywhere. If it’s just wild and fun then maybe just for the parade.
The Lesbian Pride Flag as a Pride Outfits
Not everyone knows this, but the orange-pink lesbian pride flag you see today isn’t the first draft. A “lipstick lesbian” version came out in 2010, but people felt it was too narrow. By 2018, Tumblr users pushed the updated design and it caught on. Dark orange stands for gender non-conformity. White represents unique connections to womanhood. Pink leans into love and serenity. The flag is still evolving, and honestly, that fits the spirit of Pride.
And on the body? It looks a lot like this photo. One side in warm terra-cotta trousers and a coral blazer, the other in a playful pink skirt and white tee, both grounded by simple neutrals. Toss in accessories like a bold scrunchie, a light denim jacket, or even a pink bandana. Suddenly, you’re not only wearing orange and pink, you’re flying the flag with style.
The Gay Pride Flag as a Pride Outfits
The rainbow flag is the big one. Artist Gilbert Baker stitched it together in 1978 after Harvey Milk, the first openly gay elected official in California, asked him to design a symbol. The original version had eight colors. Hot pink stood for sex, turquoise for magic. Printing issues cut it down, and the six-color version we all know took over. Red is life, orange is healing, yellow is sunlight, green is nature, blue is harmony, violet is spirit. That’s the story behind the Beyoncé of flags.
For the history nerds, check out HRC’s Pride Flag guide for the flag backstory.
Here’s the thing with rainbow gay pride outfits: I’m never happy when I try to style one. It always feels like I’m two seconds from looking like a birthday clown, so honestly, I don’t. My advice? Go so fucking loud they can’t roll back your rights!
So I was tickled to find a short from Parker York Smith! This guy is so chill, very knowledgeable and just seems like a blast! He tried a rainbow outfit and faired better than I ever could.
The Bisexual Pride Flag as Pride Outfits
The bi pride flag showed up in 1998 thanks to activist Michael Page. He wanted something that gave the community its own symbol instead of hiding under rainbow umbrellas. Pink stands for same-sex attraction, blue for opposite-sex attraction, and purple for that overlap in the middle. It’s simple, but it stuck, and it’s been waving at Pride events ever since.
Extra flag trivia if you’re into origin stories: Case Western’s explainer.
Style-wise, this look is already a blueprint. Magenta shirt, royal blue tie and pants, the bi flag itself wrapped like a cape, we need more capes in this world these days. It proves you can wear the palette in clean pieces and still let it scream bisexual pride. If you want to remix it, trade the tie for a lavender scarf or throw on sunglasses with a purple tint. The trick is keeping one color anchored, like the blue pants here, while the other shades play off it. That balance is what makes bi fashion pop.
The Trans Pride Flag as a Pride Outfit
The trans pride flag was created in 1999 by Monica Helms, a trans woman and Navy veteran. She chose five stripes that would always look correct, no matter how you flipped it. Blue for boys, pink for girls, and white in the middle for those who are transitioning, intersex, or outside the binary. It first flew at a Pride parade in Phoenix in 2000, and it’s been a staple ever since.
If you identify as a guy, here’s a post that might get you one step closer to Snazzy guy 😉
On the style side, the photo says it all. A powder-blue suit with a pale pink shirt and a clean white tie is sharp without being loud. It’s flag colors translated into formalwear, and it proves you don’t need sequins or glitter to make a statement. The vibe is confident, put-together, and still true to the softness of the flag. If you want to lean festival, swap the tie for a pastel scarf or throw on white sneakers instead of dress shoes. The structure stays, the comfort rises, and you’re still flying trans colors in a way that feels authentic.
My thoughts..
Let’s call out the big fucking fabulous elephant in the room. For whatever reason, this whole topic is treated like it’s controversial, and even more so when it shows up on a men’s style blog. Here’s my take, quick and dirty. I’ve loved, I’ve lost, I’ve grown. That’s the cycle, and it’s how people actually live. I wouldn’t dream of denying my kids or my friends the shot at love, even if it ends messy, because that’s how we learn. So who gets to say anyone else can’t love based on gender or sex? Not me. Not you. Nobody.
I don’t know you, you’re not bothering anyone, and that’s perfect. The best kind of solidarity is between people who both believe everyone should be happy, loved, and left the sweet fuck alone to do their thing. We’ll probably never meet, never talk, and that’s fine. I can’t understand what’s gained from making this (Das life) so unnecessarily difficult.
So yeah, it’s not a choice. Love is love. Hard enough to find it in the wild without a running defense from a self-important asshole with big feelings about dumbshit.
If these feelings make you angry, that’s your right; hang on to those feelings elsewhere.
Let me know in the comments if you want me to do another one of these. I loved playing with the ideas and seeing how it can trans-late, no pun intended.
Men’s accessories always help, but you need the foundation to be solid first. Click here to learn how to Dress Like you mean it! And Click Here to get the mind right!
