Best Dressed: The Top Rule Breakers of 2009

We've crowned these models the 10 best dressed Rule Breakers for 2009.

In this slideshow: Agyness Deyn, Daisy Lowe, Natasha Poly, Hanne Gaby Odiele, Noot Seear, Chanel Iman, Erin Wasson, Kate Moss, Dree Hemingway, Freja Beha Erichsen

Named one of 2007's Next Top Models by Vogue, Agyness Deyn has appeared in the world's premier magazines and has walked countless runways for big designers like of Marc Jacobs and Anna Sui. Her menswear-inspired style has earned her best-dressed titles and a slew followers. We loved when she wore her leather jacket over a sparkly cocktail dress. Just a typical Rule Breaker look on the red carpet from Aggy.

Agyness turned heads once again in a bold micro mini accessorized with a stark white blazer, matching stacked heels, and Marilyn Monroe-inspired hair.

Agyness rocked the fashion world during the Spring 2010 runway season not by walking in the shows, but by dying her signature platinum bob black. Showing off her fondness of jackets yet again, she pairs a shoulder-padded bomber with a soft babydoll dress and sexy knee-high socks.

With a name like Chanel Iman, could a girl possibly aspire to be anything other than a supermodel? How about a fashion icon? Named for her mother's favorite designer and a cousin, Chanel Iman is forever taking risks when it comes to fashion. She arrived on the red carpet for H&M's fete celebrating Matthew Williamson's line for the store in a tunic that she wore as a dress. The sparkling top she chose was a popular look from Topshop's Spring line.

Who didn't love the leggings trend? Chanel created the ultimate Rule Breaker look in a sequined pair matched with a leather bomber and sky-high ankle boots.

Chanel dressed down a flapper-style Chanel couture dress and really made it her own by adding a studded belt, footless tights, and bejeweled shoes.

London's It girl Daisy Lowe keeps busy on the runways for designers like Vivienne Westwood and Burberry, and has become an editorial favorite for such glossies as W and i-D. Off the runway, she raises the style bar with her risk-taking ensembles like this wing-sleeved minidress with diamond cutouts and a venom red bag.

Daisy went diagonal in this trompe l'oeil turtle dress, showing off her great legs and even greater smile.

Prim one day, punk chic the next. Daisy's casual version of a Rule Breaker outfit includes tight leather pants, buckle-strapped ankle boots, and a fur-trimmed floor-length coat.

Great-granddaughter of Ernest and daughter of Mariel, Dree Hemingway is both an actress and a model, and you can add Rule Breaker to the list now, too. She turned heads in Paris this past show season both on the runway and off in ensembles like this bold shoulder-padded jacket over leather leggings, which she accessorized with sunglasses from the Giles Spring 2010 collection and burgundy velvet peep-toe pumps.

Dree is quickly becoming the new queen of cool-kid style. Her defiant mix of pieces is a Rule Breaker requisite, and we just can't get over those incredible stovepipe pants.

For the launch of designer Matthew Williamson's line for H&M, Dree wore one of the collection's bold pink vests. And instead of playing the rest of her outfit down, she bravely decided to add harem pants and those amazing Alexander Wang open-toe booties.

In addition to earning a rep as one of the hardest-working models in the industry, Erin Wasson is a designer, stylist, and muse (to pal/designer Alexander Wang). A Rule Breaker like Erin could never wear just any plain old pair of jeans. Hers are slashed and worn with a menswear blazer.

Over-the-knee boots were one of the season's biggest trends. Erin takes the trend to the next level with thigh-skimming boots that almost meet her mini tank dress, allowing for the slightest bit of leg to be exposed.

Even though her look is totally unique, the pieces Erin wears are all very basic—and she likes it that way. "I'm working all day and if I have a dinner or something, I'll go from jeans and a T-shirt to maybe a simple black dress. Same heels. Same hair and makeup. I really like the idea of being utilitarian. My dream is to edit down my wardrobe and be very Japanese where you have one rolling rack and it's like your four T-shirts, your five dresses, your two pairs of jeans... I love the idea of being super edited."

In the early '90s, Kate Moss' delicate 5'7" frame ushered in a new model era and the world was introduced to the "waif." She has been a star and style icon ever since, gracing more than 300 magazine covers and inspiring us with outfits like this sheer polka-dot evening dress she wore to the British Fashion Awards Gala where she won the London 25 Award, which honors a style icon who best embodies "the spirit of London."

Kate Moss stole the show as she arrived with Marc Jacobs at the 2009 Costume Institute Gala at the Met in a silver lamé creation by the designer with a matching turban that she helped design especially for the occasion with Stephen Jones.

Kate's Rule Breaker version of the little black dress is a super sexy long-sleeve mini.

Russian beauty Natasha Poly mixes three hot trends together showing perfect Rule Breaker aplomb with a leather jacket, leggings, and studded ankle booties.

Natasha looked elegant on the red carpet in a gothic strapless gown that would make Tim Burton proud. Just another Rule Breaker proving that style on the red carpet need not be limiting.

We can all learn from Natasha. Her perfect slicked-back do, a gorgeous red pout, and a form-fitting strapless shift is simply stunning.

Model turned actress Noot Seear opted for a look off of Alexander McQueen's Spring 2010 runway for the premiere of New Moon—her first major role in a movie. A model first, Noot's style and keen fashion sense is apparent on the red carpet.

The epitome of Rule Breaker, Noot plays it simple yet chic in a white tank and leather mini. And did you notice those black booties? We'd be lying if we said we weren't jealous of her effortless style.

Channeling biker chic with a black moto jacket and shiny leggings, Noot is the ultimate Rule Breaker.

Not only does Hanne Gaby Odiele rock fabulous clothes on the runway, but she has great personal style, too. In Paris during show week she put a classic twist on her Rule Breaker style with a belted stroller jacket, but kept it bold with color.

Back in New York, Hanne is street chic in comfy bleached jeans and a plaid flannel shirt.

Growing up, Freja Beha Erichsen thought she'd be a rock star rather than a supermodel. She may not be playing in front of millions of fans, but she certainly dresses the part in a leather motorcycle jacket, skinny jeans, and a rocker tee.