Is it okay to leave your shirt unbottoned with a t-shirt or v neck under or is this look too sloppy Ray Romano esq. What shirts do you think go for this look if any?
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I think it would be a hard look to pull off unless you're in college and in your early 20s.
If you don't fall into that group, I think it's still doable. I'd say take a striped unbuttoned shirt, wear a non-white, possibly logo t-shirt under it, and roll the sleeves on the shirt. The unbuttoned shirt shouldn't have a really stiff collar so that the collar rolls a little and looks more casual.
IMO, the only way you could pull that off as a top is with shorts and casual shoes without socks as a bottom. Wearing it with pants will yield a "Dad-ish" effect and will immediately make you look older and unstylish. The shorts would need to be well-fitting, fall above the knee (i.e. not jams or the huge shorts we all wore in the 90s). The shoes would have to be pretty casual, either canvas lace-up sneakers or white sneakers.
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