How would you dress if a.) you believed you were above society’s rules—legal, sartorial or otherwise—and, b.) you knew that any day your outfit might in fact be the last you'd ever wear or, worse, immortalized in a courtroom sketch artist’s portrait? I don’t know you, but I assume you’d dress like a drapey, breezy, beautiful imbecile. See, lawbreakers are beyond reproach when it comes to style. There is not a magazine in the entire world that would run a “Who Wore It Better” with the person on the left cradling a Tommy gun on his or her hip. If you think I’m full of shit, here are twenty four reasons to believe.
Rick Morrison is a writer living in North Carolina. Follow him on Twitter here.
1. stylishcriminalslead
2. slickwilliesutton
3. rufusbuckgang
4. prettyboyfloyd
5. mockduck
6. meyerlansky
7. matahari
8. machinegunkelly
9. johndillinger
10. jessejames
11. dbcooper
12. cheguevara
13. charlesponzi
14. bonnieandclyde
15. blackbeard
16. blackbart
Black Bart
Black Bart, of stagecoach-robbing fame, was known as a “gentleman robber”, for his style and the short poems he’d leave at the scene of the crime. One such poem, below, is better than anything on Dedication 5.
"I've labored long and hard for bread,
For honor, and for riches,
But on my corns too long you've tread,
You fine-haired sons of bitches."
—Black Bart, 1877
17. billythekid
18. babyfacenelson
19. alcapone
20. nuckyhtomson
Nucky Johnson/Nucky Thompson
Nucky Thompson of Boardwalk Empire fame is based on real-life Nucky Johnson of life-so-wild-they-make-shows-about-it fame. But like anyone who’s granted a mulligan, Nucky did his style a smidge better the second time around. His sportcoats hug closer, his gel-head shines brighter and his lapel carnations bloom badder. But I’m sure real-life Nucky was still the brie’s cheese amongst his peers, so I’m not lighting a candle at St. Barnabas’s for homeboy.
21. matteomessinadenaro
22. luckyluciano
23. johngotti
24. franklucas
Frank Lucas
Frank Lucas, aka “Superfly”, was a Harlem heroine kingpin who made more per hour than he’ll ever see in American Gangster royalties. His hallmark floor-length chinchilla coat and matching hat ($125,000 total) was a purchase he made after attending a Muhammad Ali fight in a suit and seeing beta-bitch dealers rocking mink. Ironically enough, is coat eventually did him in when at subsequent fights police started wondering who the idiot in the chinchilla was and why he had better seats than Sinatra.