VMA Fashion Triumphs And Tragedies: The Top 10 Get Rated In ‘Step & Repeat’!

See how Rihanna, 50 Cent, Christina Aguilera, Gwen Stefani, Chris Brown scored on past VMA red carpets!

For almost 25 years now, there’s been no better place for the famous to “Step and Repeat” than the MTV Video Music Awards — and they’ve rarely disappointed, whether their finery is triumphant or tragic.

We’re sure to see plenty of both at this year’s VMAs — which take place on Sunday, September 7. But we took a look back with the help of Tim Gunn, Tyson Beckford, Lauren Conrad and others, at some of the best and, er, less best moments on “Step & Repeat: The Best & Worst of VMA Fashion.” Hang on tight! Here’s who we think holds it down when they hit that carpet …

At #10 is “Transformers” megawatt hottie Megan Fox, who sure lived up to her last name when she showed up in a hot-pink mini bandeau dress by Harve Leger at the 2007 VMAs in Las Vegas. In fact, we’d even bet that this appearance played no small role in taking Ms. Fox from action-movie eye candy to red-carpet starlet.

Outkast may be at #9, but they’ve proved time and time again that they know how to stand out in the crowd — especially with Andre at the helm of this fashion ship. From his orange overalls in 2003 to his classy pink and green golfer combination in 2001, he and Big Boi turn it out for every carpet under the sun. As Big Boi himself said, “We coolin’!”

RuPaul, who comes in at #8, worked it hard in 1993, proving that stunning style can come in very large packages. In a sequined, black, floor-length Pamela Dennis gown, the nearly 7-foot-tall drag queen brought some old-Hollywood glamour to the ceremony. She was quick to point out that despite the fabulous exterior, “Underneath it all, I’m just a simple girl!”

Seven is a lucky number for Justin Timberlake, who hit the 2006 VMAs in New York in a snappy three-piece suit, showing the world that the man wasn’t just singing about bringing sexy back.

Coming in at #6 is 50 Cent, who surprised everyone in 2003 by looking more gangster than gangsta in a pinstripe suit. Nuzzling in at #5 is Jessica Simpson, who makes the grade for her white-hot Miami-heat dress and short, windblown tresses in 2004. Kanye West, who went for classic glamour in a tuxedo in 2007, slides in with style at #4.

Never one to shy away from taking a risk, Rihanna rocked the carpet last year in a hot-pink, low-cut bodice gown that finds her sashaying into our #3 spot.

At #2 is the Bad Boy himself, Diddy, who made a grand entrance and looked hot doing it in 2004 in Miami. He said, “You know we gotta make a grand entrance” — and he certainly did that, disembarking from a giant yacht in a white tuxedo (with Bruce Willis rather inexplicably in tow).

And shining at #1 is the queen of style herself — and the newly minted mother of twoGwen Stefani, who has transformed herself from SoCal ska siren to full-on pop goddess. This hot momma has described getting ready for these events as being “so exciting, still!” But really how can anyone doubt the woman who started the hip L.A.M.B. line and has said, “It’s like playing Barbie, but with giant, huge, full-grown models!”

OK, those were the triumphs. And now, the moment we know you’ve all really been waiting for: the non-triumphs …

At #10, Chris Brown went for McDonald’s chic in 2006, wearing what appeared to be a uniform for the hamburger chain. On the carpet he said, “You know, I’mma let ‘em have that right quick, right?” Maybe he meant fries?

In at #9 is Paris Hilton, who decided that rocker chicken would be a hot look for the 2006 VMAs. It had too much of everything: too much fluff, too much black, too much white — and she even rocked ankle boots and gloves. Eighties prom queen, anyone?

A love triangle (har har!) of questionable fashion choices comes up next. At #8 is Kid Rock, whose fringed cowboy style left many stylists singing the blues. He is followed by 2007 sparring partner Tommy Lee, whose flasher getup in 1999 earns him the #7 spot. It’s always more appropriate to wear clothes under your trench coat, Tommy.

But it’s their shared former flame Pamela Anderson (in at #6) who tops off this unholy trinity with her 1998 getup, especially her peculiar accessory: a top hat that puts both of those guys’ looks to shame. She said the look was “so off the hook,” but really the look was more, well, off.

Former “House of Style” host Rebecca Romijn comes in at #5 with her animalistic 1998 outfit: a hairy black gown that screamed “Mortia” more than style icon. “It’s horse hair,” she said. “Somewhere there’s a bald horse running around in a field.” All we have to say is, it looked better on the horse.

In 1997, our #4 choice Busta Rhymes opted for a Far East superhero look, and then topped himself two years later with what can only be described as a yellow halter onesie.

At #3 is reformed fashion offender Christina Aguilera, who in 2003 was nearing the end of her bad-girl phase — but that pink Cavalli dress she wore that year still leaves a bad taste. “I just loved the pink off-setting the black,” Christina said — too bad nobody else did.

Lil Mama probably had a case of the terrible twos before getting ready for last year’s VMAs — which makes her a fitting #2 on our countdown. The rapper showed up in one of the most bizarre outfits ever to hit the red carpet: She was dressed like a baby, pacifier and all.

And finally, is anyone who remembers her 1999 getup surprised to see that Lil’ Kim tops our list? Let’s just say that the rest of her shirt wasn’t the only thing missing from that outfit. Kim said she “just wanted to do something that would say, ‘Look at her!’ ” She accomplished that many times over.

Will these looks be topped at the 2008 VMAs? Bet on it — and tune in to find out on September 7!

It’s a wrap! Now that the 2008 VMAs have come and gone, check out all the winners, the most surprising moments, the best red-carpet fashions and more at VMA.MTV.com.