The next time you get thrown in the slammer forget your grandmothers useless advice about wearing clean underwear. When busted for whatever illegal activity of your choice you hope to look as good as Whitey Bulger in this classic, actual mug shot from 1953. Fashionably un-aware Bulger gets him a spread in Esquire Magazine in 2011.
(via Esquire.com)

No man gets dressed up for his mug shot, as Nick Nolte and James Brown — who both went for the same disheveled-tropical look in theirs — can attest. That’s because nobody expects to get caught. So the mug shot, as it turns out, is an honest assessment of a man’s innate style. You may not posess Bulger’s stone-faced swagger, but you can still learn something here: Though you should never plan to be arrested, dress every night as if you’re going to be.
Read more: http://www.esquire.com/blogs/mens-fashion/#ixzz1Qau1npAc
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