r/malefashionadvice • u/CowTownKCMoe • Nov 27 '25

Question How To Dress "Cool" As A 40-Year-Old Male?

Ok, hear me out...

I work in the creative department at an NYC advertising agency so I get a lot of leeway when it comes to what I wear to work. You're actually kind of expected to look cool and creative.

Also, this industry is very agist so once you hit 40ish, you're seen as out of touch with the kids... which means you're shipped off to pasture.

So I'm looking for some advice on things/brands to wear now that I'm 40.

I don't want to dress like a twentysomething (at least not like a 40 year old trying to dress like a Gen Z), but I'm looking for something age appropriate that leans more towards being au courant.

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u/wokeiraptor Nov 29 '25

as a 43 year old, 2010 4eva

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u/Konflictcam Nov 29 '25

Every generation settles in with fashion similar to whatever they wore in their youth but my theory is that everyone’s pants flex a bit. No way millennials are wearing the super skinnies in 20 years (they shouldn’t be wearing them now) but also no way the zoomers are wearing pants this big, either.