The Oscars have been called the fashion version of the Super Bowl, but, trying to decide on the last decade’s greatest gowns, I decided to take a tip from March Madness instead and put them into brackets. Call it “Oscarology.” Each week, I’ll blog a different set of contests as the best gowns go head-to-head to determine which will be the ultimate champion of the ’00s.

I’ve settled on what I considered the top 32 dresses of the decade, and divided them into two divisions based on color: the Neutral Division (buffs, beiges, whites, blacks, grays, matte golds, pale peaches, and the like) and the Color Division (your reds, greens, blues, and basically everything else). Then, I seeded the dresses based on four factors: 1) design of the dress; 2) how well it fits the wearer, in terms of both personality and figure; 3) the fame of the wearer (A-listers get seeded higher); and 4) “historical significance” of the dress (basically, did the wearer win an award in it, and, if so, which one?) After the seeding, however, fame and history won’t count for anything, and I’ll compare the dresses on their own merits (factors 1 and 2).

Here’s how I seed the Neutral Division (click images for larger version):

1. Julia Roberts, 2001

Vintage Valentino

Best Actress, Erin Brockovich

This dress, long a critical favorite, combines classic lines (an almost-strapless look with a long train) with modern details (white piping that unexpectedly forms a V-neckline). It piquantly pairs menswear details like the “pinstripes” of the skirt with beautifully feminine lines. Unique and elegant, this one will be difficult to beat.

2. Nicole Kidman, 2003

Jean-Paul Gaultier

Best Actress, The Hours

Kidman’s win and fame may give this dress some traction it doesn’t deserve: While its interesting lines are refreshing, some critics derided as “lopsided” and said black wasn’t Kidman’s best color. Its draping, however, is beautiful, and the three strands around Kidman’s shoulder make for a unique touch.

3. Katherine Zeta-Jones

Best Supporting Actress, Chicago

Rarely has pregnancy looked this elegant. Being with child definitely agrees with Zeta-Jones, who was radiant that Oscar night even before she won her award. The sumptuous, Renaissance-inflected lines of the bodice would have been memorable even on an actress of less stature, and, in a design coup, the full skirt actually accentuates Baby Zeta-Jones. The slit in the skirt may be the only misstep here: while it probably was added for ease of movement, it does interrupt the flow of the skirt.

4. Meryl Streep, 2009

Alberta Ferretti

Nominated, Doubt

Streep’s marmoreal shoulders are some of her best assets, and she wisely chose a dress that would show them off. Her gown looks back to the Renaissance, with its draped off-the-shoulder neckline, and straight ahead to the deconstructed trends of today with its loose, casual lines. Add a regal updo, and Streep is the picture of an Italian countess.

5. Penelope Cruz, 2007

Versace

Nominated for Best Actress for Volver

Okay, full disclosure: I love this dress beyond all reason. In fact, I probably would have gone ahead and made it Dress of the Decade had I not decided on this ranking system. But, I think, most people would admit, there’s a lot to like here: that fluffy train, the peachy-pink hue which is just perfect on Cruz, and the fact that it’s a mermaid gown that actually works instead of looking Barbie-esque and contrived.

6. Anne Hathaway, 2009

Nominated for Best Actress for Rachel Getting Married

Armani

Though she’s had some missteps in the past (notably that bow-bedecked number she had on in 2007), in ‘09 Hathaway became a contender with this gown. Along the way, she taught us what “pailettes” meant, as her sleek dress was encrusted with them, to dazzling effect. The gown hovers between silver and white, hinting at Deco without slipping over the edge into costumey territory, and its lines make Hathaway look long and elegant.

7. Jennifer Lopez, 2001

Versace

Presenter

J. Lo made a stir in ‘01 with her NSFW gown, and though many decried the dress as another lame attention-getting device, I loved it. The difference between this gown and the infamous green Versace she wore to the Grammys in 2000 is the difference between ‘nude’ and ‘naked’: the first evokes classical art and is about the beauty of the human body; the latter is about titillation. It was nice to see a dress that celebrated the loveliness of the female breast for a change, instead of just inviting viewers to stare at some boobs.

8. Angelina Jolie, 2004

Marc Bouwer

Presenter

Shiny satin can be tough to pull off — it has a tendency to hug curves and add pounds to even the most waiflike of actresses — but Jolie did it beautifully with this 1930s-inspired gown in ‘04. The plunging neckline reveals just enough without being hootchie, while the scarf adds grace and glamour. The pearl-like color also adds to the ‘wow’ factor: it’s not stark white, which might have glared under the lights and matched poorly with Jolie’s skin tone.

9. Halle Berry, 2003

Elie Saab

Presenter

Speaking of sparkle, how about Halle Berry’s glimmering gown in ‘03? Gold is definitely her color, and the single shoulder strap is very alluring. The semi-transparent skirt teases the viewer with a glimpse of leg while it keeps the gown from being too blinged-out.

10. Helen Mirren, 2007

Best Actress, The Queen

The Dame proved that actresses over 50 don’t have to look dowdy with this cute, fresh, just-blinged enough gown. The skirt, daubed with impressionistic gold swatches, even swirled. Also, Mirren shows that dresses with sleeves can wow as well as your garden-variety strapless, halter, and one-shoulder gowns.

11. Kate Hudson, 2003

Versace

Guest; Hosted Technical Awards Banquet

Hudson shimmered in Versace in ‘03. This dress, with its cap sleeves and empire waistline, hinted at the Regency, and its lace overlay was pure elegance. The”champagne” color was lovely as well, as was the lengthy, flowing train.

12. Chloe Sevigny, 2000

Yves Saint-Laurent

Nominated, Best Supporting Actress, Boys Don’t Cry

Sevigny went for simple, classic lines in her Oscar debut. I love the crisp fabric of this dress, which I believe is silk duponi; it folds beautifully. The plunging neckline is daring, but the elegant lines of the dress more than counteract it.

13. Heather Graham, 2000

Gucci

Presenter

Graham shone in this silver gown with its abstract beaded pattern that resembled a blingier version of topographical lines. The beaded straps are a nice touch, too (as, of course, is the 50 carat diamond necklace!). Some critics found the silhouette too “cocktail,” though.

14. Hilary Swank, 2001

Versace

Presenter

Swank brought the va-va-voom to the ‘01 Oscars with this form-fitting golden gown. Just check out the pleats of that skirt! The train is the ideal length and it falls beautifully: Swank looks downright mermaidic. The fabric clings to her figure like a second skin, but she’s got the body to make it work. Some might call the color a smidge on the bland side, but I think it’s got sufficient sparkle.

15. Beyonce Knowles, 2005

Versace

Performed nominees for Best Song

Beyonce never looked more elegant than she did in this black velvet number in ‘05. The gown shows off the material to its best advantage: it’s so matte it almost appears a silhouette at first glance, revealing a beautiful cut, but then you notice the subtle hints of sheen, nipping in at Beyonce’s waist and creating lines that emphasize the length of her legs.

16. Ryoko Hirosue, 2009

Valentino

Starred in Best Foreign Picture winner Departures

This dress, though not worn by a major American star, is one of my longshot picks. Its pleats are suggestive of the ‘goddess’ trend of 2007-8, but not in a togalike or costumey way. It’s just simple, subdued glamor, letting rich fabric and graceful pleating speak for themselves.