Some fashion disasters are so bad, not even a batallion of stylists can repair them. Despite having more money than most of us will see in a decade, some sartorially star-crossed celebrities just can’t seem to get the hang of dressing well. Learn what not to do from looking at five perennial denizens of the “Don’t” lists.
There was a time that Lindsay Lohan was one of Hollywood’s freshest faces (and not in mug shots). However, she got a bit too fresh when she attended the 2004 premiere of the movie “Bobby” in Venice. Ms. Lohan wore a floaty short kelly-green sundress, stylishly oversized sunglasses, and masses of silver bangles on her slim wrists. The thing she didn’t wear? Panties. As she stepped off the boat, she gave the assembled crowd a view of her “mean girl.” In an attempt to fix the gaffe, her publicist released doctored images with pink panties painted over Lohan’s lady-bits, but the bare truth was already out there for all the world to see and no one was fooled.
Lesson learned: When wearing a short sundress, panties are emphatically not optional.
Famous for being famous more than for any impressive body of work, Tequila has little choice but to rely on just her body to get attention. Apparently dyeing her hair and hiring plastic surgeons to make her look inhumanly pneumatic isn’t enough, so she also dresses to depress whenever she steps out on the town. Her most recent horror at the Maxim Hot 100 party resembled a pair of pink and white chintz napkins artfully folded to emphasize the exploded Rhode Island Red rooster at her waist, accessorized with Bugs Bunny’s white gloves and a necklace that looked like a Bourbon Street gutter on Mardi Gras night. In case the outfit itself was too demure, she later sprawled on the floor and flipped up her skirt for photographers.
Lesson learned: Pulling your dress over your head to get attention stops being cute about the time you learn how to walk.
Simpson is a gorgeous woman at any size. Her blonde-bombshell good looks have been as instrumental to her fame as her music and her star turn in the reality show Newlyweds: Nick and Jessica, but she’s recently come under fire for her apparent weight gain. No one can fault the girl for loving the occasional ice cream cookie sandwich, but Simpson’s trouble is that she still seems to be trying to shoehorn herself into clothes that no longer fit her. The most infamous example of Simpson’s fashion victimhood were the heinous “mom jeans” she wore onstage at a Florida chili cook-out in 2009. She later confessed to Oprah Winfrey that those jeans were her “lowest point.”
Lesson learned: Wear the size you are, not the size you want to be. No one reads that tag but you.
Accomplished enough to make Wonder Woman suffer a mid-life crisis, multiple Emmy award-winning writer and actress Tina Fey seems to have it all — a loving family, a great career, a sharp wit, and the same svelte figure she had when she first appeared on our screens in Saturday Night Live well over a decade ago. There’s just one thing Fey doesn’t have: an eye for fashion. Her most egregious gaffe was wearing a satiny navy blue jumpsuit to the 2010 Met Ball. The jumpsuit itself was tragic enough, but surrounded as it was by swirling full-length gowns and acres of sequins, it looked like a fancy version of an auto mechanic’s uniform.
Lesson learned: No matter how beautiful and accomplished you are, if you don’t dress for the occasion, all people will talk about is your funny-looking outfit.
Courtney Love, lead singer of Hole and widow of Nirvana front-man Kurt Cobain, is infamous for her fashion blunders. While she may look as though she got dressed in a thrift store at midnight during a blackout, her clothes aren’t cheap. Examples of her atrocious taste abound, but one of the more recent Love sightings was at the Roberto Cavalli’s “Just Cavalli” event at Milan’s fashion week in March 2010. Wearing an ill-fitting stained gray shift, a black cardigan, and a headband that may once have been a pair of tattered fishnet hose, Love managed to look both ridiculously expensive and just plain ridiculous.
Lesson learned: Money can’t buy taste, but it can buy a conspicuous amount of tastelessness. Not everyone’s clever enough to know the difference.