03/18/2010 05:12 am ET Updated May 25, 2011

What the Aughts Taught Us: The Decade's Most Stylish Women

One Sunday afternoon in 2000, my twelve-year-old self wandered into one of Saint Louis' hipster consignment stores and found a pair of poppy red DKNY bell bottoms I was convinced would change my life. In the sea of pastel North Face fleeces, denim miniskirts and whatever the precursor to Uggs were, my bright red pants, which I so preternaturally paired with a black turtleneck and brown clogs, would ricochet me right out of the stylistic hemisphere of my junior high, and into the life of the other "Best Dressed" of 2000 I'd read about in the Vanity Fair magazine I had just started reading. Fashion Week, St. Petersburg, and Oscar afterparties were in my immediate future, I was sure.

Now in 2010, I remain confident such adventures are right around the corner, but have come in the past decade to realize that perhaps the poppy pants I once thought held the key, do, in fact, not. In the past decade, my style has metamorphed from poppy panted punk to peasant skirted hippie (before Sienna, thankyouverymuch ) to an uncomfortable period where I toyed with maybe-I-should-be-suburban-preppy-too, finally arriving in college at the conclusion that the women who looked the greatest followed their instincts and didn't think too much about their clothing after that, preferring instead to go lead interesting lives, which has lead to a lot of neutrals, a lot of sequins, and a lot of fur in my closet.

A lot can change in a decade, both in stylistic abilities and aesthetic perceptions of what is aspirational. If I have evolved somewhat from my preteen days, I believe our general sartorial consciousness has as well. I offer below the ten women who did the most to bring us from red hiphuggers to the Roger Vivier flats and shift dresses I'm so in love with now, and thank them for pushing our wardrobes up to happier heights--

1. Enough cannot be said about the freedom, the taste and the daring that Anna Wintour has given the fashion world at the helm of American Vogue. Plenty of magazines have always decreed it "okay" to mix high and low, spring and fall, print one with print two. But Anna, and her creative director Grace Coddington, proved it and exalted it again and again in their ethereal, exuberant spreads each month. Market editor Meredith Melling Burke finds items, from paisley picnic baskets to tribal bib necklaces to Thakoon flowered tunics, that go far enough beyond the smorgasbord of stilettos and skinny belts in other magazines to make them look like the Jersey Shore counterpart to Vogue's West Village cool woman. Anna lives her magazine's spirit in a uniform of fur thoughtlessly and perfectly matched with silk florals, real and candy jewels against each other, and knee high croc boots. Anna and your team at Vogue-- thank you.

2. Lest I start to seem like a one trick pony, I herewith dispense of Michelle Obama references after this post for at least the rest of January, but cannot leave her off this list. Michelle walked a fine tightrope during the campaign of appearing inoffensively, powerfully, uniquely and chicly dressed, and she pulled it off for the most part with aplomb. At a barbecue in middle America wearing an H&M shift dress with a cardigan around her shoulders, Michelle didn't look like she had given a second thought to what she was wearing, although she looked great, and this was absolutely appropriate for the moment. During her inaugural dance with Barack in fairy-tale Jason Wu, she looked elated to be wearing her dress, but more excited to be with Barack. Michelle, as evidenced by her penchant for excellent emerging designers -- Wu,Thakoon, Maria Cornejo , Isabel Toledo -- is sophisticated. What makes her most aspirational is how truly complimentary rather than primary fashion is to Michelle's life of purposeful leadership in her personal and professional life. Michelle wears fashion, it never wears her.

3. With the same promise of a January moratorium on mentions after this post, a nod to Carla Bruni. Whether strumming her guitar on the piano bench of the Paris apartment she shares with President Sarkozy in jeans and a cashmere sweater or wowing the world in purple Dior skirt suits during a visit to London, Bruni lives Diana Vreeland's dictate that elegance is refusal. Undoubtedly, most stylistically inclined women envy the closet they imagine she has, but one of the last things that seems to interest Bruni is shopping. Perhaps this is somewhat the French in her- shopping seems to be a sport for many American women, and Bruni gives the impression that she has more interesting things to do, like gallivant around Egypt with her presidential husband and purr out songs about her fifty past lovers. Merci, Carla, for proving that your life might look more fashionable if it isn't solely dedicated to fashion.

4. Anne Hathaway is one of the most elegant spirits of her generation. Calm and Kors shiftdressed in the wake of a breakup that would have reduced many women to sweats, a hoodie and Converse every day, Anne seemed to continue on her elegant trail not in a vindictive "see-what-you-screwed up" sort of way, but simply because it's who she is. Her nice, neutral fabrics, straight brown hair, and occasionally risky necklines and hemlines embody the Ludwig Mies van der Rhode quote stenciled on the Design Within Reach store near my office that I love -- "To have an interesting plainness is the most difficult and precious thing to achieve."

5. A tie between Sienna Miller and the Olsens for bringing in the grunge of the aughts, this time not dependent on flannel and Doc Martens, but on looking like you've just slumped out of a night of partying in Morocco, Milan or Miami in a combination of American Apparel, your jetset mama's closet, and an Hermes boutique. Also, for the ethos that showering is for people with way too much time on their hands. These girls stuck it to the concept that you have to spend a lot of money to be chic, and ushered in an era of having fun in your fashion outside the confines of a haute nightclub that reverberates to this day. Also, although Intermix recommends every week without fail in it's "Luxe List" that I buy something from Mary Kate's brianchild Elizabeth + James, copious amounts of credit should go to Ashley for The Row- a truly useful, timeless and highly edited collection of thoughtless chic that makes for excellent investment shopping.

6. Anne della Russo, fashion editor at large at Vogue Nippon, is simply unable to do, wear, or create something unspecial. A recent perusal of her Sartorialist and Garace Dore shots shows her in massive one-shoulder Lanvin at a 9AM fashion show, strolling down the street in feathered skirts and a penchant for the Balmain studded wrap heels before, during and after their time as The Balmain Studded Strap Heels. Without ever looking precious or too done up, della Russo manages to always, always look like she wants to. There will be no paparazzi shots of her caught off guard in something awkward, and one suspects this is less because she takes an amount of time to prepare that the Olsens would scoff at and more because she knows herself unequivocally, and won't put something in her closet that doesn't hold up to her exacting, exuberant standards.

7. Aerin Lauder Zintenholfer's choices are never flashy or over the top, but always looks perfectly suited for a moment one would want to be in -- a turn in a convertible out to the beach, a garden party, a stroll around Central Park on a Sunday afternoon. Without looking like a caricature out of a Slim Aarons photo, Aerin's style embodies the good life for those not particularly interested in adventurous fashion but with looking polished, appropriate and most importantly, looking happy. If a man's crisp button down, khaki flat fronts and Chanel flats don't say happy day with my family, I don't know what does, and no matter what she wears, Aerin always has this air.

8. Tory Burch proved several things during the past decade, but most notably that ubiquitous didn't have to mean safe. Legions of women clamored for her Northern African and Middle Eastern inspired tunics, dresses and later her lifestyle products, and she thereby gave everyone license to be unique, even in their lemmingness. I like to think of Tory as the advanced option for the Ugg -North Face-denim miniskirt girl from my, and I suspect your, junior high school. Props also to Tory for creating an empire based on something so simple as the ballerina flat, and for giving it a kick that hordes of subsequent imitators have failed to match.

9. Even after she stopped blessing our living rooms as Carrie Bradshaw on Sex and the City, Sarah Jessica Parker continued to teach us what Carrie had -- that a tutu will earn you a first glance walking down the street during daylight hours, that a silk skirt looks cooler with a t-shirt, that if you're going to wear a nameplate necklace, you better be damn proud of it, and that just about anything looks better with a touch of irreverence.

10. Liya Kebede has been one of the decades rising and most interesting talents. Originally tapped by Tom Ford for an exclusive contract to walk his Gucci Fall/Winter show in 2000, Kebede has since then graced countless magazine covers and runways, become the first African-American representative Estee Lauder has ever had, served as a World Health Organization ambassador for Maternal, Newborn and Child Health, and has most recently launched a children's clothing line called LemLem . Her substance augments her style, which is fierce and confident without being brash, and she serves as an excellent role model for young women looking to merge high form and high function.

Another look I (very) briefly flirted with from the red pant thrift store was a bright red t-shirt with the word "Hucci" emblazoned in gold across the front in the classic Gucci font. I was getting ready for an eighth grade dance, and it seemed like a good idea at the time. It is now the single most cringe-worthy thing I've ever festooned my body with, and was worn with hooker boots and black pants, natch. It quite vigorously ended up back at the same thrift shop I'd bought it from (Avalon Exchange in St. Louis, if any of you are now inspired to go shopping) probably less than a week after I'd purchased it. Similarly, it's not that the decade hasn't offered up as many turquoise polyester tube tops and Britneys as it has Aerin Lauders and inspired Lanvin/Gap getups, it's just that they are not the taste I'm left with as a new decade begins, not what I've culled, and not where I'll return.

So let's all move onward and upward, do the ladies who've inspired us these past ten years proud, and perhaps try and usurp them in the next decade with something a bit better than poppy-colored hiphuggers.