Grammy Fashion: 40 Outrageous Outfits

Since the beginning, the Grammys -- music's most celebrated soiree -- has also been a huge night for fashion. Here, we salute 40 brave artists whose stylists have worked overtime to make sure they turn heads and make a fashionable impression on Grammy night. Check out the pics and tell us who gets your biggest cheers and jeers.

Lady Gaga proved she was a star at the 2010 Grammys by actually carrying one on the red carpet. The Judy Jetson look won raves from fashion critics, but we can't imagine her feet were a fan of those crazy shoes.

Jennifer Lopez gave us some serious jungle fever in 2000! Her tropical, flowing Versace gown with the infamous plunging neckline had everyone talking -- once they all stopped gawking, that is. We still can't believe how good J.Lo's body looked in that dress, but we have a feeling that's what she was going for.

Man or Muppet? Cee Lo Green really got into character at the 2011 Grammys when he dressed like a giant fowl-type creature during his performance with his Muppet backing band. Watch your back, Big Bird.

M.I.A. had two head-turning fashion moments in the same night. Not only did she perform flaunting her pregnant belly in bold polka dots, she hit the red carpet in a blue get-up that appropiately resembled children's clothes. Too bad her kid was a boy, or else he could have worn it.

If Kanye West had just closed his shirt, this outfit would have been a little less tragic. Instead, he looks like he walked out of Blaxpoitation remake of "Saturday Night Fever." A little disco never hurt anyone but this is going too far. Button up, Kanye!

There are two rules to follow when getting dressed for a major awards ceremony: make sure your dress doesn't show your underwear, and make sure your dress ISN'T your underwear. Seriously, Toni Braxton, if the front and back of your "dress" are attached by a glorified thong waistband, it's not a dress.

Alicia Keys must have been in on some secret that we didn't know about. Apparently underwater garden parties were all the rage. There isn't any other way to explain the weird green flowy silk stuff and floral embroidery everywhere. The plain white tank top and green belt remain a mystery.

From the looks of it, Pink decided to wear more eyeliner than clothes to the 2002 Grammys. We don't even think the singer's barely-there outfit would have flown at the Moulin Rouge! And while we don't question her talent, we are wondering... Where did the rest of her pants go?!

Three years after her 2002 hit, Sheryl Crow was still soaking up way too much sun. The belly-baring dress she wore to the awards in 2005 was more blinding than a solar explosion... and far more devastating. This outfit was too much skin and not enough win.

Britney Spears does her impression of a pretty princess in this flouncy, leaf-encrusted, half bedazzled leotard gown on stage at the Grammys in 2000.

Tween dreams the Jonas Brothers never fail to disappoint on the red carpet, and always look suave and put-together -- well, almost always. What's up with the sparkly jacket, Joe? Only Michael Jackson could have pulled that piece off.

Beyonce's style always turns heads, be it in a good or bad way. Unfortunately, this is not one of her best looks. The unusual necklace-collar is distracting, but even worse is the too-tight dress. With too much makeup and strange hair, Beyonce's not looking very golden here.

Back before Rihanna got "Hard," she was just an up-and-coming pop princess from Barbados. So, of course, Rihanna fits the part by wearing a mermaid dress! She looks like she should be hanging out with Ariel more than her current superstar entourage.

Carrie Underwood shows off her stunning white and gold, floor-length dress on the 2009 Grammys red carpet. This look is "outrageous" in the sense of "outrageously good."

Even if Katy Perry woke up in Vegas, she'd be hard-pressed to find such a head-turning look! Her outfit is gorgeous. With the not-too-pink dress, her old-Hollywood hair, her subtle (but glam) makeup and the awesome bling, even the girls might be lining up to kiss her!

Gwen Stefani has never been one to be tamed -- not even by pregnancy! The glowing mom-to-be looked gorgeous in a leopard print gown that flattered her baby-body in all the right places. Out of all her Grammy peers, Stefani was definitely the cat's meow.

Nothing says "I'm a rising pop star, take my music seriously" more than a laced-up, ultra-v-neck, belly-button-baring top and hair that looks like you just stepped off a Jamaican cruise ship. Both styles have their place, Christina -- but not at the Grammys.

Most of this outfit is fine -- normal, even. The black and white suit looks good and fits well. But R. Kelly just had to go and screw it all up with the bandit mask. That's one piece that would definitely look better trapped in his closet.

Avril Lavigne wears her love for all things rock on her sleeve -- and inside her jacket. In 2003, the poppy, punky princess urged Grammy-goers to "rock on" and served up her battle cry with a healthy dose of the rebel-lite attitude that made her famous.

Paisley was nowhere to be found in Brad Paisley's ensemble, but the country star didn't disappoint when it came to other eye-devastating patterns. We're convinced he stole Grandma's upholstery to make that jacket lining. Let's just say his all-flora outfit was nothing to fawn over.

Britney's most recent look at the 2010 Grammy Awards took bodysuit + lace combo to an unfortunate place. We're sure the Dolce + Gabanna dress looked good in her bedroom, but that's probably where it should have stayed.

Mary J. Blige is no stranger to daring outfits, but this poodle-yellow jacket atop a fringy canary-colored dress, and -- oddly -- green heels, is certainly one of them.

While simple is usually better, John Mayer's black suit ensemble is missing a little something. Maybe he could have opened his jacket to show some more of that purple? Perhaps dress his style up with some snazzy (but subtle) jewelry? John's personality is certainly unique; he should dress the part!

Madonna's arguably in the best shape of her life. Rocking her chained purple corset with a matching long-sleeved leotard and a Farrah Fawcett feathered do, Madonna's dancer-meets-bondage look could be the envy of girls half her age. We're with her ... except for the calf-high pantyhose. Where'd that come from?

For all we know, Evanescence singer Amy Lee may have just started out with a bubble-gum pink princess dress. But when she decided to goth it up with a roll or two of electrical tape and then randomly rip the bottom, it went downhill fast.

We salute Coldplay's worn-and-torn take on Sgt. Pepper's. The band wasn't too stuffy in suits, too crazy with their colors, or too far-out with their fashion choices. Instead, their motley military jackets were the perfect look for their 2009 Grammys crusade: they took home three awards that year.

Apparently, TLC waited until the very last minute to decide to attend the Grammys. Only having a few square yards of black and white fabric laying around, they were able to throw together a few "skirts" and bras to keep themselves somewhat covered. Phew! Crisis averted.

Maybe they were making a statement. Maybe they were trying to literally blend into the red carpet. Maybe they wanted to just be known for something different than that treadmill music video. Whatever the case, OK Go's ensemble, made of your grandma's curtains, just comes off strange.

It should be back to the rainforest for Destiny's Child. Seriously, as awesome as those six Grammys look, maybe classier outfits would have done the job. It's not even the green that's the problem. A rule of thumb -- the fewer leaves on your outfit, the better.

What else could be expected from a girl who showed up to the VMAs in pasties? Compared to Lil Kim's other outfit adventures, the red-leather motorcycle jacket and white bikini top remains one of Kim's more conservative red-carpet ensembles.

A little leopard print goes a long way. Lots of leopard print gets you laughed at. A head-to-toe leopard ensemble of bell-bottoms, a Persian rug jacket, a top hat, and a leopard face exploding from your chest would be simply ridiculous on anyone but Bootsy Collins.' His trademarked star sunglasses just add to the class!

Former 'American Idol' judge Paula Abdul hasn't always carried herself with the grace of a goddess, but at the 2009 Grammys, she tried to at least look the part. Sorry Paula, but your loud, yellow toga with tin foil accents just didn't deliver on the red carpet. Good luck on Mt. Olympus.

Usually-dapper Usher takes from apparent style muses Frank Sinatra and Jesus Christ as he mixes a blindingly white, ill-fitting suit (sans-jacket) with a tie-dyed tie and gold chains galore. And are those... wingtips? Stick with basic black next time, Usher, and you'll have the ladies screaming "Yeah!"

Chris Brown pummeled the competition in this crisp, red and white ensemble. For us, the outfit is a hit! His modern take on a traditional suit left him looking sharp, and the color scheme -- right down to his sneakers -- ensured he wasn't drab. Needless to say, Brown just can't be beat.

Maybe Nelly thought he was going to a basketball game instead of the Grammys. Maybe he thought he was gonna get too hot in therre if he wore a suit. Or maybe he just thinks that, since he's number 1, he can get away with anything.

Maybe we shouldn't be so much concerned with his fashion than with T-Pain's safety: How can he see anything with those sunglasses on? And couldn't he at least have gotten them in a brown shade to match the rest of his sloppy look?

Leave it to Macy Gray to wear a t-shirt boldly proclaiming her goofiness. The rest of the ensemble is just as jarring: the dead polar bear across her shoulders, the embroidered jeans, the pink boots. The fact that her rose-tinted glasses are the most normal part of this outfit says a lot.

Other artists should be green with envy that Andre 3000 can pull off this get-up. His lime-green, Native American-inspired stage costume was too feathered, too beaded, and just too much -- but that's what Andre is known for! We applaud him for managing to look gaudy and good.

It's the CreaCher from the Black Lagoon! Known for her outrageous outfits, Cher celebrated the awards' 50th anniversary in a gown that was more swamp than romp. If we could turn back time, we would have advised Cher to hire a better stylist.

Future Man has won five Grammys as part of Bela Fleck and the Flecktones, but it looks like the "Drumitar"ist has his sights set on an Oscar too -- as Best Supporting Actor in the upcoming "Pirates of the Caribbean" flick. Looks like someone walked the plank and fell off the fashion deep-end.