John Huba

Go for it. This combo was long considered a don’t, but now it’s a completely fashionable weekend look. The key to getting it right is to incorporate different shades of denim and simple styles. (That means no matchy-matchy separates or, say, a studded denim jacket with a tiered jean skirt.) “Dark jeans with a lighter chambray shirt work best,” says Ciepluch, who recommends breaking up the top and the bottom with a belt.

To buy: The Limited 917 Skinny jeans, $75, Steven Alan top. Loft heels. Ben-Amun bracelets.

Is It Okay to Wear Last Year's Jeggings?

Keep jeans that are… 

  • Jeggings
  • Trouser cut
  • Bright
  • Black or gray
  • Cropped
  • Boyfriend-style

Toss jeans that are…

  • Whiskered
  • Super low-rise
  • Patched
  • Relaxed cut
  • Distressed
  • Ripped

For the rear views of many of the jeans shown here, see Jeans With Flattering Back Pockets.

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