I wear fitted hats, as do a lot of people I know. I hate having to deal with adjusting the hat, and I hate having the opening in the back. A fitted hat to me is much much more comfortable then a regular adjustable hat, also add the fact that fitted hats are usually a bit higher in quality.
As far as the shirts being to big, everybody has their own like. I personally don't like a shirt clinging to me, unless its like a muscle shirt and i'm workin in the yard. When I go out, I wear a shirt that is a little bigger then me, not 3x but probably 2x.
Then the jeans, I don't wear my jeans hanging off my butt or anything, but I do wear a size bigger so they don't hug my parts... As i'm sure a lot of guys would agree with me, it gets very uncomfortable when they can't move.
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