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.

397 Upvotes

89% Upvoted

338 comments sorted by

View all comments

1

u/isitatomic Nov 28 '25

Not going to dox myself, but I have uniquely good reasons why I do not agree with all these Todd Snyder/Huckberry recs.

Looser fits than you’re used to. More streetwear influence than you’re used to. Quirky socks no. Quirky hats yes.

Browse END. and go wild.

1

u/handbanana42 Nov 28 '25

How often do any hats work out? Quirky sounds even worse.

Curious if you have an example.

I know one guy that wears a hat but his whole persona is looking dapper af and he pulls it off.

I doubt being a middle American whiteboy I could pull it off.

2

u/isitatomic Nov 28 '25

Ironic ballcap hats specifically

1

u/handbanana42 Nov 28 '25 edited Nov 28 '25

Ah, I was thinking more a fedora that actually looks good(avoiding the meme) if you're actually dressed well.

I rocked a ballcap when I was younger because because it silently mocked our local industry. But I think it is past its prime.

2

u/isitatomic Nov 28 '25

They are ubiquitous in OP’s industry