y2k outfit advice

Jip

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I'm going to a y2k themed party on Friday and it seems like the perfect opportunity for windpants, but I'm having a hard time coming up with an outfit that reads as legitimately y2k-themed, incorporates windpants as the best possible option for bottoms AND looks good. I'm 6'0, skinny, dark hair, man.

Unfortunately I'm finding it very easy to do this with baggy jeans, but that feels like such a wasted opportunity lol. The outfits I've tried with windpants are mostly looking better with jeans, and I don't want to wear a second-best option just to force it you know?

The only decent idea I've found is: unzipped black adidas windbreaker, black adidas pants, baggy white t-shirt, chain necklace, backwards white ballcap. It's a bit of a sleaze vibe but it works

Other than that everything else looks like the windpants are out of place or don't really seem that y2k or don't look good, like I tried black adidas pants (no stripes), baggy white t-shirt under a graphic t-shirt, misc accessories, but the problem is that if I swap the windpants for baggy jeans, the outfit looks both better and more y2k.

The best baggy jeans look i figured out was baggy light colour jeans, tight branded armani exchange shirt with orange sleeves/grey torso (terrible shirt but the different colour sleeves and torso feels y2k to me), puka shell necklace, sporty sunglasses, backwards ballcap. But again, feels like SUCH A WASTE to not wear windpants to this thing.

And I guess one thing that could help is if anyone has male celeb photos from 1998-2004 I could reference that would be great, I'm having a hard time finding any on google, seems like they're always wearing jeans :'( . The key thing here is I'd rather go for a boy band / teen movie antagonist vibe than a gym teacher vibe.
 

Cubitus the Chatty

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Maaan o' man 😅 some people got problems 🤣 .... Sry not meant in a bad way....

But it's just that easy....... If you don't feel fine in the outfit just don't wear it 🤷

It's a fight only in your head, the struggle between looking good / matching or feel fine ..... So ..... A party is never cool if you're not comfortable.... So don't force you to "live your fetish" but just live it.

What if you wear an outfit what's maybe your plan B but for everyone else it looks like you've overdone the research like Plan A++? 😅

At this time joggers weren't that cool anymore, in my country (Germany) we sayd "Popperhosen" ... Popperpants like fast to fu#(...... In my hood, your timespan, definitely Baggy jeans, T-shirt, Hoody. Important to have a hood not just a pullover. The wider the pants the cooler you are. No sport shoes but "Skater shoes" .... Airwalk, Etnies, DC, Dickies and so on, important to have fat laces ....... That's my time between 98 and 04......
 
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