Best Boots to Wear With Cropped Pants & Styling Tips

Hi Deborah,

I have a pair of dressy, cropped flare pants. When it’s warm, I wear them with mules, but now that winter is here, I’m not sure what boots to wear. What do you suggest? Thanks, Dana

Hi Dana,

This is always confusing, so let’s break it down. The goal is to cover your exposed legs so you stay warm and to elongate them too, so you look elegant. It’s all about balance, so here’s what you do.

1. Choose Boots that are High in the Shaft

Visualize a short ankle bootie that ends at the top of your ankle bone. Now imagine wearing cropped, wide-leg pants that sit about 2-4″ above your ankle. There’s going to be a big chunk of your leg exposed. Ankle booties leave a gap between the top of your boot and your pant hem. Not only will you freeze in winter, but the ample space will make your legs look short and squat.

The key is to wear a tall boot to cover your exposed leg. This means a boot with a high shaft to cover this gap. You can see below that my booties have a high post and go up under my cropped pants.

If you don’t want any skin showing when sitting down and your pant leg slides up, wear a sock the same color as your bootie.

boots with cropped flare pants

2. Boots Should Narrow as They Rise Up the Leg

In addition to having a high shaft, your boots should narrow as they rise up your leg. If your boots are wide around your leg, when they meet your pant hem, your leg will look like a big, wide block. Sock booties were invented for this very reason. They are tall in the shaft and slim and stretchy around the leg,  so they fit nicely under cropped flare pants and create a chic, feminine silhouette.

You don’t have to wear sock booties, but your boots should have a high enough shaft that they slip under your hem or at least come close to your pant hem, so there’s a minimum gap, and again, they need to narrow around your leg.

Other tips to elongate the legs and balance your look when you wear booties with cropped pants:

  • Heels – even a small block heel will make your legs look longer.
  • When your booties are low contrast or the same color as your pants, your legs will look longer.
  • Pointy-toe boots will elongate your legs more than round or square-toe boots.

And that’s how you wear boots with cropped pants in winter.

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