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What Shoes to Wear With Jeans, Dresses and Wide-Leg Pants

The right shoe is mostly about proportion. Look at where your hem ends and how wide it is, then use this cheat sheet.

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Wide-leg pants

Wide hems need a shoe with some presence. Pointed flats, block heels or platform sneakers peeking out at the front all work. Full-length wide-legs look best with a little heel so the hem skims the floor. Cropped wide-legs suit loafers and minimal sneakers.

Straight and bootcut jeans

Almost anything works: loafers, ankle boots, white sneakers or slingbacks. With bootcut jeans, choose a heeled boot so the flare falls cleanly.

Skinny jeans

Tall boots over the top, ankle boots that meet the hem, ballet flats or chunky sneakers for balance.

Midi dresses and skirts

Midi lengths cut the leg at its widest point, so show some ankle or foot. Strappy sandals, pointed flats, slingbacks, knee boots that disappear under the hem, or clean sneakers for a casual look.

Example: a floral midi, three ways
  • Floral midi dress
  • White sneakers (weekend)
  • Tan knee boots (fall)
  • Nude slingbacks (wedding)

Swapping the shoe changes the occasion more than any other piece.

Matching colors

Shoes that match your pants lengthen the leg. Shoes that match your skin tone do the same with dresses. White, tan and black are the three colors that cover almost every outfit.

Frequently asked questions

What shoes go with wide-leg pants?

Shoes with a pointed or platform toe that peeks out: pointed flats, block heels, loafers with cropped styles, or platform sneakers.

Can you wear sneakers with a dress?

Yes. Clean white or neutral leather sneakers work with midi and maxi dresses for a casual daytime look.

Try it on your own clothes

Photograph your favorite shoes and get three outfits built around them.

Get 3 outfits free
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