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9 Dress Shorts Looks

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 Dress Shorts

Dress Shorts

Jaden Smith

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

 Dress Shorts

Dress Shorts

Cuba Gooding Jr.

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

 Dress Shorts

Dress Shorts

Perez Hilton

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

 Dress Shorts

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

Dress Shorts

Kelsey Grammer

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

 Dress Shorts

Dress Shorts

Nick Zano

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

Dress Shorts

Lapo Elkann

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

 Dress Shorts

Dress Shorts

Perez Hilton

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

 Dress Shorts

Dress Shorts

Alexander Wang

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

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