Clothing guilty pleasure - Things that everyone finds ridiculous/tasteless but you enjoy wearing anyway

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True & Honest Fan - Core
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I'm a tremendous fan of 1930s menswear, when the explosion of Roaring '20s innovation ran smack into Depression-era make-do-and-mend. I love the range of fashion-forward details, extensive pattern mixing, and especially the vocabulary of tailors' tricks that bring a strong presence to almost any physique.

Almost any physique.
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Slouch hat with the right-side brim pinned up, so it's less cumbersome than a regular wide-brimmed sun hat. Today, it's obviously not a suitable apparel for anyone not in Straya or Southern Africa, but I like the convenient combination of size and sun protection it offers
 
Heinrich Himmler said:
For the summer, I have a collection of Hawaiian shirts that everyone in my life hates.
Some are pretty normal, in blue, green and red/pink tonalities; but others have pretty outrageous patterns and violently clashing color combos, and hurt the eye just by looking at them.
My wife has a pure and unedulcorated hatred for them, and has tried to throw them away a couple of times already.
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Oh man, this is me so hard.
I like wearing colourful shirts, and my friends just egg me on and see if they can find increasingly hideous ones. I have one with a street scene on it, and under UV the neon signs glow. It's my most treasured item of clothing.

When I was in Bali last, I bought a more subdued and tasteful (for me) hand-made batik shirt in a kind of pink and blue mix - haven't worn it much yet.
 
I'll say that for day to day stuff, Western wear is my go-to. Vertical stripes and bootcut jeans, baby. The hat and bandana less often but...they're there.
Sylvie Paula Paula said:
Despite being a guy, I enjoy women's clothing - Japanese fashion subcultures, mainly. I have to wear women's outfits anyways, but I'd dress myself up a lot more if it wasn't a pain in the ass for multiple reasons.
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But would you parachute into enemy territory with ladies undergarments on like this suave motherfucker did?
 
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I dress like a normie most of the time but I have a tasteless love of anything retina-searingly neon. I have a neon pink/blue/highlighter yellow Adidas hoodie and a turquoise/lime green/neon orange Nike hoodie I got from a vintage sale and I love wearing them even though I’m fully aware they’re garish as all hell. I’m also a sucker for anything more normie tier that has palm trees and/or flamingos on it.
 
i wear hoodies and pants every time i leave the house, no matter what. the fact that i haven't passed out from standing in 1000 degree heat like that is a miracle
 
I'm in my 30s and have a 6 pack.

good luck putting a shirt on me in the summer.
 
As I've come closer and closer to getting /fit/ I find myself wearing active wear as casual clothes more often.

Also I love BDU pants and I've worn bomber jackets since I was 19
 
A friend got me a pair of retro My Little Pony print ugg boots a few Christmases ago. I love those things. I almost live in them when it's cold.

I also had an extensive collection of 90s dark fantasy style t-shirts, the ones with the skulls and the dragons, but most of them have worn out and I haven't been able to replace them yet.
 
Sometimes I wear my old Umbro shorts as boxer shorts because I'm a dirtbag.
 
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