I will get us started. My favorite pair of worn in have had for years jeans, a soft cotton tshirt that fits well...not too big, not too tight and my fave pair of New Balance or Nike sneakers (if I have to wear shoes.)
Jeans (or shorts if hot), sneakers, t-shirt.
If I could only wear one thing from now on it would have to be just my beach towel. or nothing at all.
This might sound strange, but if I had to pick one outfit I would probably pick a suit. Not like a full blown tuxedo or anything, but a pair of comfortable dress pants, a blue shirt and a jacket. I don't actually find suits to be terribly uncomfortable, and I figure if I'm going to be wearing something over and over again, it might as well be something I look good in.
Definitely jeans and a T-shirt. Or, if I could get away with it, PJ bottoms and a T-shirt. ;)
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