this post was submitted on 21 May 2026
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me_irl
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I think the fundamental issue is that I'm a T-shirt kinda guy and nothing except a baseball cap goes right with a T-shirt. A lot of the other hats need something like a suit to make sense.
Go shirtless!
But also, I wear my Aussie hat with a T-shirt - it's a little more subdued than a cowboy hat*, so it works I think :-)
* My friends still call it my cowboy hat.
A Gilligan bucket hat would be fine. Or a gardening-type straw hat.
I used to wear skater beanies/egg shells with tshirts. I also used to dress more like a skater though.
A bucket hat can work. I can't pull it off personally but I've known people who rocked it