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8 of the Chicest Gangster Girlfriends in Fictional History

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Here at Racked, we're dedicating this week to the kind of fantastical shopping that most of us only get to experience in dreams (or at 80%-off sample sales). Taking a page from casino parlance, we'll be talking a lot about "whales," those big spenders who feel perfectly comfortable dropping tens of thousands of dollars every night on roulette, or, in our case, on Cartier. Welcome to Whale Week 2013.


Photo: IMDB

There are a lot of downsides to being a gangster's girlfriend (like the constant fear for your life), but one upside is that looking and dressing great seems to be part of the job description. Turns out all that dirty money can buy quite the extravagant wardrobe! In honor of the recent release of Gangster Squad, and in tandem of our own Whale Week celebration, here now we pay homage to the fictional women who nailed the role.—Jihan Forbes

Emma Stone as Grace Farady in Gangster Squad
Grace Faraday's style is prim and ladylike during the day, but once night falls, Miss Thing serves up a piping hot dish of bombshell glamour. Sort of like, Emma Stone, actually.


Photo: IMDB

Uma Thurman as Mia Wallace in Pulp Fiction
Mia Wallace's effortless style had that perfect dash of bad girl grit. With her black bob and simple-chic sartorial taste (easy white buttondown, cuff links, and cropped black trousers, for example), she had the mysterious cool-girl look down pat. After all, she managed to make getting stabbed in the chest with a horse needle full of adrenaline look (relatively) glamorous. That said, please don't stab us in the chest with a horse needle full of adrenaline.


Photo: IMDB

Diane Keaton as Kay Adams-Corleone in The Godfather
Let's give it up for the educated woman who married into a mob family. Kay Adams-Corleone was a lady though and through, with her teatime-ready frocks, strand of pearls, and always perfectly curled hair. Way to keep it cute in the midst of mob madness, Kay.

Drea de Mateo as Adriana la Cerva in The Sopranos
Who could forget the unabashedly sexy Adriana la Cerva? The long fingernails, the big hair, the over-sexed persona all wrapped up in a tight leather dress. Who knew a strong dark brow with blonde hair could look, well, sort of stylish?


Photo:IMDB

Madonna as Breathless Mahoney in Dick Tracy
Madonna served us all the va-va voom we could ask for as Breathless Mahoney in Dick Tracy. In slinky frocks boasting plunging décolletages and look-at-me red lips, Breathless was a great representation of a sexpot diva in control of her sexuality. What could be more stylish than that?


Photo: IMDB

Lymari Nadal as Eva Kendo Lucas in American Gangster
When we think of Eva's style, the word "opulence" comes to mind. Feathers, furs, jewels—she had it all. As the signficant other of NYC kingpin Frank Lucas, the Peurto Rican beauty was only too happy to outfit herself in the finest threads.


Photo: IMDB

Michelle Pfeiffer as Angela de Marco in Married to the Mob
Angela de Marco was the quintessential '80s mob wife (or in this case, widow). She rocked big hair, strong shoulder silhouettes, bold prints, colorful eye makeup, and about 10 pounds of funky, chunky jewelry.


Photo: IMDB

Faye Dunaway as Bonnie Parker in Bonnie and Clyde
As part of the actual gang, Bonnie Parker might be the most badass of gangster girlfriends. Bonnie is the OG of 'Ride or Die' chicks, as she did both rocking a shiny blonde bob and sweet beret. Bonnie's sweaters, long, A-line skirts, and trademark scarf around the neck gave her that deceptive good-girl look. Because you would never expect a woman dressed as a secretary to hold you up at gunpoint and pocket all your coins.
· All Whale Week coverage [Racked]