Pretty Woman’s Rodeo Drive (Baby!) Glam Gets a Modern Update

By Erin Donnelly
August 25, 2008

While we’re sure there are a lot of things hookers know about (ahem), a knack for putting together chic and tasteful designer outfits usually isn’t one of them. Unless, of course, a certain wealthy client decides to foot the bill for a ridiculously lavish Beverly Hills shopping spree, complete with dressing room montages set to the music of Roy Orbison. We refer, of course, to Pretty Woman, the classic Julia Roberts/Richard Gere rom-com that made hooking look like, if not a promising career choice, then at least a surefire way to meet handsome, rich, tragically misunderstood men. But enough about dubious love stories—let’s talk about those clothes! From that legendary red gown to Vivian’s dotty polo dress to, yes, those boots, we’ve found modern-day interpretations of your favorite streetwalker styles. Now, will that be cash or charge?

The Red Dress: Got a hot date and a limo waiting to whisk you off to the opera? Skip the LBD and stand out from the crowd in a glamorous red gown. For formal occasions, keep the long length with BCBGMAXAZRIA’s stunning Strapless Pieced Satin Gown or Atria’s Jessica Rabbit-esque 1228 Prom Dress. Faviana’s smoking-hot Sweetheart-Fitted Cocktail Dress sports a shorter length. And for an everyday option inspired by Julia’s gown, look to this ruby-red Ruched Jersey Dress from Suzi Chin Maggy Boutique.

The Boots: We know what you’re thinking: Can I really pull off mid-thigh black patent leather hooker boots? Yes, yes you can. Over-the-heel boots are actually making a comeback this season (wear them over skinny jeans if you’re not up for flashing thigh), and with a little reining in—like laying off the patent—they can look strong and sexy, not slutty. Our picks: Steve Madden’s budget-friendly Over-the-Knee Zip Boot; Stuart Weitzman nappa leather boot; Ted Baker’s edgy Over-the-Knee Platform Boots with branded trim; and LD Tuttle’s slouchy-cool Serpent Slouch boots. Feel free to skip the pantyhose. 

The Polka Dot Dress: Even if your social calendar doesn’t include hobnobbing at the polo matches, a brown and white polka dot dress still deserves an Arsenio fist pump. Fall for dots big and small in Forever 21’s Polkadot Chiffon Dress, the retro-rinsed Penelope Dress from Marc by Marc Jacobs, the Lacie Eyelet Dress from Delia’s, and Mori Lee’s flirty strapless Dotted Dress. For a high-fashion riff on the style, go with Robert Rodriguez’s more graphic Silk Polka Dot Dress.

And if you still feel the urge to let your inner bad girl out to play, throw a tied white men’s shirt over this electric blue Racer Back Dress from Bop Basics, let your hair down (permed or not), and have at it, Cinder-%$@!-rella.  

Stuart Weitzman - 50 Cube - Nappa ($535.00)

Zappos.com is proud to offer the Stuart Weitzman - 50 Cube (Black Nappa) - Footwear: Ultra chic over-the-knee boot in nappa leather with elastic stretch for a great fit. Pull-on design. Leather lining. Rubber sole. Made in Spain.