A Pants Primer

The bottom line on the best cuts and shoes to wear with each.

  • Skinny gives the most shoe options—it’s great with flats or heels, tough or feminine.
  • Straight looks great with flats, or try it with a chunky sandal or an oxford.
  • Boot Cut is the most universally flattering style and works best with a heel.
  • Cropped works with flats, but a heel is flattering. Try a nude shoe to really elongate.

Pants are a problem. I tweeted this seemingly innocuous statement from a fitting room at the Gap (yes, the Gap), where I recently found myself paralyzed by indecision. The slim cropped pant looks fresh (and yet oh so Audrey Hepburn) but doesn’t work with longer tops, and it presents a footwear problem in inclement weather. Wide trousers are staging a comeback—just when I’ve invested in longer T-shirts and ballet flats that work so well with skinny jeans.

We’re shopping in an age of fashion democracy, and while it is great to have choices—nearly two dozen pant cuts are currently on the shelves at Gap alone—there is something to be said for simpler moments in style, like back when the universally flattering boot cut was the only way to go.

I’m not alone. By the time I left the store (empty-handed), my pants tweet had sparked a firestorm of online comments from women confounded by the range of silhouettes available in stores today and perplexed about what shoes to wear with each.

I talked it over with Macy’s Minneapolis fashion office manager and trend correspondent Laura Schara, who listed her favorite pant styles of the season, including boot cut, skinny, and skinny cropped.

I asked for clarification. “Do you consider cropped and ankle length one and the same?”

“I guess I do,” Schara said. “But now I see why everyone is confused!”


Here’s some advice:

  • Capris belong in the giveaway pile. First and foremost: Capris are shorter than cropped pants. They hit at the widest portion of the calf, which is unflattering to virtually everyone other than runway models, who wouldn’t be caught dead in capris anyway. Best alternative: cropped pants, which hit around the ankle. To show more skin, try Bermuda shorts, a skirt, or a sundress.
  • Longer legs = leaner look. Cropped pants make your legs look shorter. A lift—even a small wedge—will elongate. For a fresh twist, try the J.Crew approach: wedge ankle boot with slim cropped pants. No socks!
  • Round toe with cropped pants. That said, a girl needs her flats. No one knows that better than Mall of America fashion expert Sara Rogers, who logs a lot of miles on the job. She likes the look of a round toe with cropped styles. That includes ballet flats, oxfords, or Converse sneakers (which she owns in several colors).
  • Boot cut demands a point. The easiest way to wear boot cut pants is with a heel. Still, I marvel at the way Rogers makes a flared bottom work with flats. The key, she says, is a pointy toe. “It elongates the leg line.” Rogers gets some boot cuts tailored for flats and leaves others longer—they should nearly skim the ground—for a heel.
  • Nude shoes have magical powers. Nudes complete a look without demanding attention, so legs can take center stage.
  • Skinny jeans do not make you look fat. When they fit, skinny jeans actually create curves, Schara points out. They also give you the most footwear options, from boots to ballet flats to pumps or platforms.
  • Accept it. There is no one pair of pants or shoes that works with everything. We need options. And so the shopping continues . . .