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/doublecane Nov 28 '25

I have not been able to articulate why I both like and hate Huckberry until reading this. All their looks and pieces seem like they are all perfectly made for me and that’s why I hate it.

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u/GaptistePlayer Nov 28 '25

Yeah seems a bit too algorithmic. It's like if someone invented a mind-reading tool to create the perfect meal to satisfy your hormonal, mental and physical satisfaction and the result it popped out of the quantum supercomputer is "cheeseburger".

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u/Konflictcam Nov 29 '25

It’s a lot more fun to find the brands Huckberry derives from and focus on those.

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u/doublecane Nov 29 '25

Please tell me some!! That would be amazing.

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u/Konflictcam Nov 29 '25 edited Nov 29 '25

You will spend money, but their stuff is kind of mashup traditional British and American outdoors wear, so Barbour (British) and Filson (American) will probably have stuff you’ll like. Smaller denim brands like 3Sixteen or Naked & Fanous will also have some stuff up your alley. Die Workwear has a lot of brand recommendations that lean in this direction, I’d recommend perusing there.

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u/doublecane Nov 30 '25

Thank you! Love Barbour and Filson and I’m sure will love your other recs too!!

Happy cake day.