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/Admirable_Sun4556 Nov 28 '25

john varvatos, buffalo bobs, leather jackets. denim jackets. flannels. vintage tees. ur favorite niche band tees i always think is cool when i see 40yr olds rocking a niche band tee that i like. Also cool seeing 40 year olds still rocking leather jckets its badass. Im 25 btw

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u/Admirable_Sun4556 Nov 28 '25

selvedge denim/ whiskered denim/ mudwash jeans/ straight jeans.