tlmd_20361541

They don't call them short-shorts for nothing! But how short is too short? Check out who wears them better than others.

34 photos
1/34
Randres
Reailty TV star Brooke Hogan could probably class it up a bit by adding an inch or two to her hemline.
2/34
Getty Images
Jessica Simpson could work the Daisy Dukes, but this look is pushing the envelope. This striped velour pantsuit is too short, too tight, and too 6th-grade for our taste.
3/34
odalys
Mariah Carey's shorts look like they were painted on for her performance at the Teen Choice Awards last year. C'mon, Mariah, it's a family show!
4/34
You didn't really think Lindsay Lohan was going to end up on the sassy end of things, did you???
5/34
Getty Images
If you can draw your eyes away from the neckline for a few seconds, you'll see why Pamela Anderson ended up in this photo gallery. (Hint: the shorts are an issue, too.) T-rash-y.
6/34
Daniel
The ruffled sleeves and sash give Selma Blair's pantsuit a retro, flirty vibe.
7/34
mislay
Kristin Cavallari, who is bound for MTV's The Hills, pairs these navy shorts with a loose, embroidered top for a chic bohemian look.
8/34
Daniel
Jenna Dewan stepped up her fashion game and kept these short khakis stylish with a loose ruffled top.
9/34
familia
Pairing sequin-covered shorts with black tights is a stroke of genius that only Lily Allen could pull off.
10/34
WireImage
As if these ballooning shorts weren't bad enough, Juliette Lewis saw fit to add hot pink footless tights to the mix. Call the fashion police!
11/34
Getty Images
Hilary Duff's simple black shorts may be short, but paired with this silk red top the casual look gets an upgrade.
12/34
WireImage
Color us stunned, but former porn star Jenna Jameson keeps these short shorts decidedly sassy thanks to the cute jacket and tank top... you know, for modesty.
13/34
Getty Images
The graphic print and tailored cut of Kim Kardashian's short pantsuit keep the whole look classy and flirty.
14/34
Getty Images
High School Musical's Vanessa Hudgens is clearly going for a look with the black fringe top, clunky accessories and jeans shorts. We're just not sure it's the right look for her... or anyone, really.
15/34
Getty Images
As if Heidi Montag's shorts weren't short enough, she then had to roll up the hem to get them juuust riiight. Roll them back down, Heidi.
16/34
Getty Images
While Fergie has been known to cross the line from time to time, this pantsuit strikes just the right balance between chic and sexy.
17/34
yunior
Gold top? Check. Grey ankle boots? Check. Black leather shorts? Check. Is Gwyneth Paltrow forgetting anything? Oh that's right ... taste.
18/34
jorge perez
Blake Lively is making quite a fashion name for herself. The loose shorts and detail on the otherwise simple midnight romper keep this look fresh.
19/34
Getty Images
In lesser hands, a black-on-black outfit with leopard print heels could come off as trampy, but this is Kate Moss we're talking about.
20/34
Getty Images
Britney Spears, a graduate of the Madonna School of Fashion, sadly looks like a cheap knock-off in her top hat and fishnets.
21/34
WireImage
Teen star Miley Cyrus pulls off a more grown-up look with oversized top and knee-high boots that manage to work with the shorts instead of against them.
22/34
Getty Images
Amazingly, Anne Hathaway managed to take some very short shorts and wind up with a rather ho-hum outfit. We'd expect a little more pizzazz from this fashionista.
23/34
victor
Even if (and that's a big if) Katie Price zipped up her purple velour hoodie a few inches, there is still no way this outfit belongs on anyone other than a very small child from the '70s.
24/34
jorge
Granted, Gisele Bundchen's jean shorts leave little to the imagination, but frankly when you're a supermodel you can pull pretty much anything off.
25/34
Randres
Katy Perry can get away with almost anything because she's, well, Katy Perry. Yes, Perry's old school bathing suit style outfit with gloves and gi-normous detailing on the top is ridiculous. But that's Katy Perry. QED.
26/34
Getty Images
On anyone else we would hate this ensemble. But you've got to hand it to Gwen Stefani... she can pull it off.
27/34
odalys
The tulip hemline on Chloe Sevigny's shorts adds a sublime touch to the pantsuit. The oversize jacket even manages to give the whole look an office suit quality.
28/34
Randres
Rihanna's tragedy of an outfit should have stayed off the blue carpet and out of our minds. The lacy short pansuit looks like a cross between a fly girl and a mourning Sicillian matron.
29/34
Maje
Eva Longoria Parker's tailored shorts in crisp white make this look summery and chic.
30/34
Getty Images
The Hill's Lauren Conrad certainly couldn't be accused of any real missteps with this citified look, but there's something about the flowy top and the folds within the shorts that doesn't sit quite right.
31/34
BELKYS MARRERO
You might remember Keshia Knight Pulliam as Rudy Huxtable from The Cosby Show. She may be all grown up, but her fashion sense could use a little maturing. That low-cut printed shirt absolutely destroys any hope these classy black shorts might have had.
32/34
gilbe
While it's true that the shorts may be the least of Amy Winehouse's problems, you've got to start somewhere.
33/34
WireImage
Deal or No Deal's Brooke Long should have walked away from this sales pitch... shorts with matching top in a size too small. While we admit the shorts aren't the biggest problem in this outfit, they certainly aren't helping.
34/34
Getty Images
How could we not include Austria's premier fashion guru? If you had Sacha Baron Cohen's legs, you would flaunt them too. But, as with most things Bruno, the hemline goes a little too far.
Contact Us