And, finally, the dresses go head-to-head . . . uh, train-to-train? Bodice-to-bodice? Well, anyway, I paired them up and selected the victor based on style alone, blocking out the wearer’s head when necessary to keep me focused on the gown. I looked at several pictures of each gown in different poses (those below are just for reference) and in different lights to make sure I got the best impression of it and wasn’t making a judgment based on a single picture that might not show a gown off to its best advantage.

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(1) Julia Roberts 2001 vs.  (19) Ryoko Hirosue 2009

It’s an easy win here for Roberts: those classic lines handily beat out Hirosue’s gentle pleats. Hirosue’s dress is pretty, but Roberts’s Valentino blends elegance and casual sportness in a memorable combination. The pinstripes on Roberts’s train cunningly accentuate that “V” neckline, whereas Hirosue’s train is less ethereal than it could be.

(Plus, you know something’s a great dress when lil’ munchkins want to wear it for Halloween . . . five years later. This kid has great fashion sense, plus one awesome mother.)

Winner: Roberts ‘01

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(8) Angelina Jolie 2004 vs. (9) Halle Berry 2003

On closer inspection, both these dresses have their flaws: Berry’s is not fitted well around the bosom (ouch!), and the silhouette of Jolie’s borders on the boxy. The resplendent golden glow of Berry’s gown can’t outdo its busy-ness, leaving the viewer not sure where to look; the height of the translucent skirt (going all the way up to her hip) is distracting when viewed from the right. Jolie ekes out a win.

Winner:Jolie

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(5) Penelope Cruz 2007 vs. (12) Chloe Sevigny 2000

Over-the-top glam meets understated elegance in a close match. Chloe combines chic with sexy, her full, flouncy skirt and matte black allowing her to get away with a very daring neckline, but ultimately Cruz comes out on top with her memorable pairing of couture and girly frou-frou.

Winner:

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(4) Meryl Streep 2009 vs. (13) Heather Graham 2000

This one’s an easy victory for La Streep. The beading on Graham’s gown is exquisite, but its low neckline and short train say “night at the club,” not “Oscars.” Streep’s gown, meanwhile, is all elegance, and it displays one of her greatest physical assets: her marmoreal shoulders.

Winner: Streep

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(6) Anne Hathaway 2009 vs. (11) Kate Hudson 2003

Hudson’s dress is lovely, using delicate embroidery and transparent overlays to great effect, but it doesn’t have quite the same “wow” factor as Hathaway’s. In nearly every picture, Hathaway’s skirt drapes around her legs, forming a perfect silhouette as its half-moon train falls on the red carpet. Its pearly luster gives it a pop that Hudson’s gown lacks.

Winner: Hathaway

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(3) Catherine Zeta-Jones 2003  vs. (14) Hilary Swank 2001

Swank glows, but her golden gown just can’t compare to the awesomeness of Zeta-Jones’s. Seriously, if all maternity wear looked this good, there’d be a lot more children in this world. Even with the unfortunate slit in the front, Zeta-Jones’s gown reigns supreme, with its barely-there dusting of rhinestones adding glamour and its sparkly straps emphasizing the wearer’s bosom. It’s no small feat to turn a third-trimester belly into a fashion statement, but that’s what this dress does.

Winner: Zeta-Jones

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(7) Jennifer Lopez 2001 vs. (10) Helen Mirren 2007

Demure takes on daring with this matchup, in which both dresses coincidentally have a two-piece look about them. Though Mirren’s dress shows off her remarkably athletic figure (at 60!), on closer inspection the silver beading on the bodice weighs it down, and the blotches on the skirt look too much like stains. It’s an easy victory for Lopez.

Winner: Lopez

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(2) Nicole Kidman 2003  vs. (15) Beyonce Knowles 2005

Interesting things happen when you put these dresses side-by-side — like a chanteuse who’s been in one movie beating out an A-lister known for her red-carpet savoir-faire. It’s a shocking win for 15th-seeded Knowles, as the sheer shape of her gown makes Kidman’s dress look busy and cluttered. That daring how-does-it-stay-up? neckline! The sweep of that skirt! This, my friends, is design, whereas Kidman’s dress has too much going on in the name of being “interesting” to work well as a whole.

Winner: Knowles ‘05

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(1) Halle Berry 2002 vs. (16) Jennifer Garner 2004

Garner’s orange is utterly crushed by Berry’s justly-famous burgundy. Her iridescent skirt, with the odd large ruffle on its train, doesn’t quite match with the soft shirring of the bodice and the slim, leg-hugging lines of the pencil skirt. As fond as I am of the bright shade, I have to admit that this gown’s just not nearly as iconic as Berry’s number.

Winner: Berry

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(8) Marcia Gay Harden ‘01 vs. (9) Keira Knightley ‘06

This battle of the burgundies is a close one. Harden brings the classic glam, while Knightley opts for couture-inflected pleats and folding. That unfortunate, bladder-shaped fold over Knightley’s bodice is what gives Harden the edge.

Winner: Harden

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(5) Nicole Kidman ‘07 vs. (12) Salma Hayek ‘05

Hayek is the surprise winner here: Kidman is long, lean, and lovely in her red column, but the too-long streamer in the back and the hint of glittery trim detract from the clean look of her gown. Hayek shines in an unusual shade of midnight blue in a sexy yet distressed gown that accentuates her figure.

Winner: Hayek

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(4) Hilary Swank ‘00 vs. (13) Katherine Heigl ‘08

This was a close one: both gowns are exquisite. Heigl rocks the bright red like nobody’s business, and the “shoulder loop” adds a touch of piquancy and fun to her dress. But Swank is every inch the princess in her ball gown, which might well have inspired Princess Tiana’s. And the rich olive green shade keeps it from getting too girly.

Winner: Swank

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(6) Kate Winslet ‘07 vs. (11) Renee Zellweger ‘01

Both these dresses bespeak casual elegance, and their rarely-seen shades of mint and buttercup make them stand out. It’s a close one, but Zellweger wins out for the vibrancy of the yellow and the effortless lines of her vintage gown. That dress looks comfortable as well as chic.

Winner: Zellweger

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(3) Kate Winslet ‘02 vs. (14) Charlize Theron ‘00

This is how you can tell I’m a (straight) woman: I find Theron’s dress too sexy for the red carpet. I love the design, I love the color, and I like Charlize, but the low cut and flimsy fabric would make me want to cover my children’s eyes, if I had any children. So Winslet breezes past, even though her stunning red gown would have been a match for even a more formidable competitor.

Winner: Winslet

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(7) Gwyneth Paltrow ‘07 vs. (10) Reese Witherspoon ‘07

This is perhaps the most interesting matchup, as both dresses are so unique. Much as I love the muted fabric and multicolored layers of Witherspoon’s skirt, I’m going to have to give the win to Paltrow. The silhouette of her gown is classic Oscar dress, but the rest of the design takes a 180 from tradition with some fabulous pleating work. Paltrow looks like a deconstructed sunburst, in the best possible way.

Winner: Paltrow

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(2) Hilary Swank ‘05 vs. (15) Laura Linney ‘01

Two simple gowns with exciting twists go head-to-head here.  While the lines of Linney’s red Valentino approach perfection, Swank’s gown is the more unforgettable. It’s full of little eye-catching details, like the unexpected asymmetry of the back and the crisscrossing bands across the waist. Who would have thought a high-necked, long-sleeved gown could bring so much drama?

Winner: Swank

To see the updated bracket, click below:

Oscarology Sweet Sixteen