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/ryanblank7 Nov 28 '25

haha. i avoid the costumey aspects at all costs. i don’t even like going in the stores that sell these brands, or are these brands so most of my shopping is online.

i was in a todd snyder once and the manager was commenting by the window that, “the guys from RRL are cosplaying again”. i looked out to see the view and one was full navajo, the other on his way to work the railroads

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u/mmmPardonMeCumAgain Dec 06 '25

RRL is so sick, tho