Crookery has always been a part of the New York mentality (Oh, hell, the American mentality), and although it yields national villains like Bastard Bernie, it also has produced some of the most iconic images of style for generations—at least in Hollywood. While glorifying crooks is not an R29 virtue, appreciating their style certainly is. We already see some of you mentally scrunching your nose as your read this, so allow us to elaborate.
Clyde Barrow and Bonnie Parker, Bonnie and Clyde
If ever a bloodthirsty, bank-robbing duo deserved an acquittal based on future fashion choices, it was definitely these two.
Phyllis Dietrichson, Double Idemnity
Barbara Stanwyck vamped it up (Those bangs! That lipstick!) for this thriller. Her look was so smokin' that her lover gladly offed her hubby for some insurance cash.
Moses Pray, Paper Moon
With his dashing three-piece suits and suave signature hat, Ryan O'Neal put the con in icon.
Butch Cassidy and the Sundance Kid, Butch Cassidy and the Sundance Kid
Whether in cowboy hats and jeans or wool suits and bowlers, this pair of crooks made bank and train robbing look like nothing more than a healthy dose of male bonding.
Thelma and Louise, Thelma & Louise
These bad-ass gals are the perfect combo of country and rock n' roll. Watching them lead a chase from the law makes us realize that sexy style isn't just for the city. Country girls can look tough and hot, too.
Tom Ripley, The Talented Mr. Ripley
We totally understand that whole murder/stealing someone's identity thing when it affords you the Euro-chic wardrobe it does for Tommy boy.
Tell us that Tim Hamilton hasn't stolen his striped prison-wear inspiration from the McDonalds' masked thief, and we're liable to laugh in your face. We also love the large brimmed hat and red gloves; It's all about how you accessorize.
Three words: Sharp. Black. Suit. Gets us every time.