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9 Dress Shorts Looks

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Was Jaden Smith trying to start a shorts-over-pants trend when he attended the 'After Earth' premiere in Japan?

Dress Shorts

Jaden Smith
These subtly patterned shorts were the perfect choice on Cuba Gooding Jr. for a casual day out.

Dress Shorts

Cuba Gooding Jr.
Perez Hilton was dressed like a young schoolboy in a vest, tie, and shorts at the 2008 MTV Europe Music Awards.

Dress Shorts

Perez Hilton
A tank top and pink shorts seem more appropriate for the beach than the red carpet, but that's Perez Hilton for you!

Dress Shorts

Perez Hilton
Kelsey Grammer matched his fiancee's look with this blue button-down and white shorts combo.

Dress Shorts

Kelsey Grammer
Tennis anyone? Or perhaps this is more croquet attire. Can't deny that faded red (a.k.a. pink) dress shorts will always be a preppy staple.

Dress Shorts

Nick Zano
Lapo Elkann looked very summery in his beige shorts, linen button-down, and straw hat during Milan Fashion Week.

Dress Shorts

Lapo Elkann
The button-down looked innocent enough. But the pink shorts and lace-up boots were outrageous! Then again, it's Perez Hilton!

Dress Shorts

Perez Hilton
If you can rock a pair of dress shorts with a sport coat, well, congratulations Alexander Wang.

Dress Shorts

Alexander Wang
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