Although she probably intended to look whimsically sexy and fashion forward, Courtney Love‘s appearance at the 2nd Annual amfAR Inspiration Gala tended more toward a blast from the past… and not in a good way.

With its translucent material, flirty ruffles and slit up to there, Courtney’s dress resembles what an Old Western saloon showgirl might wear… under her real clothes (read: Lady of the Night?) The lacing up the bodice fails miserably at covering her chest, while the translucency of dress reveals the ominous shadow cast by her underwire bra. We’re glad you showed up to support AIDS research, Courtney, but we wish you’d left the skanky cowgirl undergarments at home!

Courtney Love at the 2nd Annual amfAR Inspiration Gala

Jemal Countess/Getty Images


Yes, we know that actress Jada Pinkett Smith has her own heavy metal band. But on her recent visit to Fox & Friends, her choice of outfit had us rocking out… of the room. We’re a firm believer in rocking whatever outfit one chooses, and Jada’s ensemble looks like a watered down version of what a heavy metal badass would wear. While a black leather jacket with zippers slashed across the front is certainly badass, the cropped princess sleeves on hers definitely detract from the optimal effect. Combined with pants that could have come out of [lastfm link_type=”artist_info”]MC Hammer[/lastfm]’s black tie collection from the 80’s, it’s a look that pulls the plug out of our amp.

Jada Pinkett Smith Visits "FOX & Friends"

Astrid Stawiarz/Getty Images


Did someone invite Cruella DeVil’s niece to the premiere of Mr. Popper’s Penguins? No, actually, that was actress Kat Kramer, whose dalmation/Flintstone-inspired dress earns her a Fashion FAIL. The dress features a large black triangular detail that pulls the neckline down in an asymmetrically awkward fashion and points, unfortunately, to her crotch.

Kat Kramer - Premiere Of 20th Century Fox's "Mr. Popper's Penguins"

Kevin Winter/Getty Images


Normally, sequined dresses fall under appropriate red carpet attire. However, for the premiere of Super 8, actress Jaime King used the opportunity to wear something that screamed… well, just screamed.

As if the fact it was a shapeless shift wasn’t enough, Jaime’s dress was adorned with thousands of shimmery sequins in orange, baby pink and black– resulting in her resemblance to a slightly sunburned koi fish. Our eyes are swimming… with tears, as we behold this scaly-looking eyesore.

Jaime King attends the premiere of "Super 8"

Kevin Winter/Getty Images

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At the 2011 CMT Music Awards, actress Nicole Kidman was a lovely vision… from the neck up. Unfortunately, her chosen outfit was another story… a story with four parts that didn’t make sense together. Crafting her ensemble from bric-a-brac scraps of an old striped velvet dress from the 80’s and a nude miniskirt layered with a sheer black skirt with a slit, Nicole finished off the look with strappy periwinkle sandals and gray nail polish. One word: Blech!

Nicole Kidman - 2011 CMT Music Awards

Credit: Jason Merritt/Getty Images


During her fragrance launch at Debenhams in London, England, Kim Kardashian sported an eye-popping skintight dress with poufy shoulders and a gold-tasseled belt. Most notably though, the triangular cutout along her midriff produced an odd protrusion of stomach flesh… which is why she’s the first to earn the honor of being in our Fashion FAIL photo album!

Kim Kardashian's Triangle of Doom

Credit: Gareth Cattermole/Getty Images


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