I'm rather picky about hats because not all hats suit me. My snapbacks and New fitted hats have to be black. The brim can't be too curved in the style of a trucker hat. I prefer just a slight curve or a flat brim, but I think I've started to lean toward the slight curve. What I do to bend the brim is I basically push the two corners of the brim together. It creates a great look. I think squarish brims suit me more than circular brims, however.
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Assuming it isn't a straight brim cap, I don't think there's anything wrong with wearing a baseball cap. I often wear a well fitted cap with a cardigan and feel as though it's a good casual look.
I'm a huge car guy and have a bit of an outdoorsy style and recently found this brand: http://www.gasolinecaps.com/shop/
What do you guys think? I love the idea of a vintage plate cap.