How to Find the Most Flattering Shorts for Your Age
They're tricky, but I support your right to bare legs. Think of shorts as a summer version of trousers or a tailored skirt and accessorize accordingly. (No flip-flops!)
By Adam Glassman

Photo: Richard Majchrzak/Studio D
Short
Inseam: 2.25"
Length: Hits upper thigh
Age Range: 35 and under*
These shorts show lots of leg, so keep the top modest. A stacked heel adds a polished vibe.
Shorts, Sandro, $220. Top, Raoul. Bag, Vince Camuto Signature. Shoe, Paul Smith.
*If you are genetically blessed with gorgeous legs, disregard all age rules!
Length: Hits upper thigh
Age Range: 35 and under*
These shorts show lots of leg, so keep the top modest. A stacked heel adds a polished vibe.
Shorts, Sandro, $220. Top, Raoul. Bag, Vince Camuto Signature. Shoe, Paul Smith.
*If you are genetically blessed with gorgeous legs, disregard all age rules!

Photo: Richard Majchrzak/Studio D
More Options for Short Shorts

Photo: Richard Majchrzak/Studio D
Mid-Length
Inseam: 4"
Length: Hits mid-thigh
Age Range: 45 and under*
Perfect for a garden party or a festive lunch. Just make sure they're not too tight in the thighs.
Shorts, 10 Crosby Derek Lam, $375. Jacket, Nic + Zoe. Top, Ann Taylor. Shoe, J. Crew. Clutch, Penelope Chilvers
Length: Hits mid-thigh
Age Range: 45 and under*
Perfect for a garden party or a festive lunch. Just make sure they're not too tight in the thighs.
Shorts, 10 Crosby Derek Lam, $375. Jacket, Nic + Zoe. Top, Ann Taylor. Shoe, J. Crew. Clutch, Penelope Chilvers

Photo: Richard Majchrzak/Studio D
More Options for Mid-Length Shorts

Photo: Richard Majchrzak/Studio D
Long
Inseam: 11"
Length: Hits at or below the knee
Age Range: No Limit!
This length flatters most women, and with a dressy top and accessories goes from day to night.
Shorts, Talbots, $60. Top, ICB. Clutch, Zac Zac Posen. Shoe, Tod's.
Length: Hits at or below the knee
Age Range: No Limit!
This length flatters most women, and with a dressy top and accessories goes from day to night.
Shorts, Talbots, $60. Top, ICB. Clutch, Zac Zac Posen. Shoe, Tod's.

Photo: Richard Majchrzak/Studio D
More Options for Long Shorts

Photo: Richard Majchrzak/Studio D
Try This...
Instead of a dress! This striped set by C. Wonder is stylish, fun and far less prone to wardrobe malfunctions than a mini of the same length. Add heels and glam sunnies and you're good to go.
Top, $118, and shorts, $98; CWonder.com
Unless you work in a creative environment, don't wear shorts to the office.
Pumps or stilettos with shorts are trashy, not classy. Choose wedges, stacked heels or flats instead.
Use self-tanner to make your legs look smoother and slimmer. My fave: TanTowel Self-Tan Towelette Full Body Plus ($27 for a five-pack; TanTowel.com). It makes your legs look airbrushed!
Top, $118, and shorts, $98; CWonder.com
Adam's Tips
From the July 2014 issue of O, The Oprah Magazine