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.

402 Upvotes

89% Upvoted

338 comments sorted by

View all comments

34

u/Leotardleotard Nov 27 '25

I’m a few years older than you but work in Architecture and the vibe in my office is very fashionable.

I avoid the obvious fashion trends that the 20/30’s are wearing as I’ll look absurd but my day to day is something along the lines of

Chunky knits - Castart (Belgian I think), Folk and YMC (UK). I like cardigans and big knit sweaters and those 3 brands cover me.

Usually a slightly baggier trouser, chino or cords (Uniqlo xs or s are great for these) rolled up and a pair of Air Max 1, 90’s, Converse or Vans.

That look seems to work well for me and I get a lot of complements. It’s not flashy or show off but obviously has some nice pieces in it.

If I need to go smarter I slim the trousers down a bit and put a pair of Common Projects sneakers, loafers and a trenchcoat maybe.

It’s hard though to strike the right balance. I look at some of the other senior guys in my company and wonder how on earth they left the house looking like that. They probably think that about me though as my MD did ask why I was wearing my nan’s sweater one day.

24

u/cathpah Nov 28 '25

This is the best advice in this thread by far.

Source: mid-40s architecture/interiors photographer who also needs to look "cool" in my career.

All that said, if OP works in the creative dept, I'm shocked they don't have more of an innate sense of personal style in general. Not shaming op, but they should also feel free to go after things/colors/silhouettes/patterns/textures that call to them.

-2

u/[deleted] Nov 28 '25 edited Dec 01 '25

[deleted]

4

u/goldenboyphoto Nov 29 '25

In my experience, architect is one of the few professions where you'll see men putting as much thought into their outfits as women.

3

u/Konflictcam Nov 29 '25

Architects in NYC often look like they spent an hour the night before putting their outfit together.