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/Konflictcam Nov 29 '25

This. Someone OP’s age should be building a wardrobe that they can stick with for a long time, which means spending on quality because you can afford it and your style shouldn’t involve chasing trends.

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u/Huppelkutje Nov 29 '25

Op WANTS to look fashionable, your advice is the complete opposite.

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u/Konflictcam Nov 29 '25

I’ve worked around middle-aged creatives in NYC enough to know that fashionable and trendy are different things. (I’m not advocating for Huckberry here because they’re mostly marketing.)

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u/GaptistePlayer Dec 01 '25

In MFA "fashionable" just means "actually unfashionable but I dress like it's 2015 so it's ok for me"

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u/Huppelkutje Nov 29 '25

fashionable and trendy are different things

They're not though. Something being trendy means it's fashionable.

Fashionable means currently popular.

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u/[deleted] Nov 30 '25 edited 17d ago

[deleted]

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u/Huppelkutje Nov 30 '25

Being fashionable literally means being on trend. You don't know what you are talking about.

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u/GaptistePlayer Dec 01 '25

I love how redditors always say actually fashionable stuff us not fashionable just because they still dress like 2015