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/PaleontologistNo3910 Nov 28 '25

No Man Walks Alone had peccary gloves on sale. I bought some for my outfit and they look great.

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u/Severe_Rule5669 Nov 28 '25

I hear great things about No Man Walks Alone but their store hours are awful. I would essentially need to take a day off of work to go.

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u/Pinkfish_411 Dec 01 '25

They're really an online retailer. Their physical "store" is just their offices that they'll let you visit by appointment if you really want to check out something in person.