How to wear ankle cowboy boots pictures

alexander wang ankle boots - Maegan/Flickr Maegan/Flickr

Updated January 10, 2017.

Do you fall in love with a new pair of ankle boots each year but wonder how you can wear them so they are flattering? They are some fashion watchers' least favorite styles of women's footwear. They earn this reputation not for how they look themselves, but for how they are worn, which is often in the most unflattering way possible.

What you see on the runways and in fashion magazines does not always translate well for your own body and lifestyle.

For example, ankle boots with cropped leggings or shorter tights is a definite "don't" for women who have shapely calves. Even women who are on the thin side have to be careful as the combination seems to chop inches off your height while adding bulk to your legs.

So what should you wear with ankle boots?

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Stylish Ankle Boots and Booties

There are combinations that work much better than others. Here are a few of favorite looks that are flattering on most women.

Ankle Boots with Long Skirts

Whether they're flat or heeled, ankle boots and long skirts or maxi skirts are classic combinations for fall. It's best to pair them with long skirts that are on the fuller side, but ankle boots can be paired fairly successfully with long skirts that are more narrow. Whichever style you prefer, the key is to show no leg. If the skirt isn't long enough to cover the top of the ankle boot on its own, add a pair of tights.

Short Skirts and Ankle Boots

This look is definitely a little more difficult to pull off, because a lot of women don't like their legs.

But it works well because instead of showing no leg, you're showing a lot of leg, while the real trouble comes in when you only show a little leg. Look for skirts that are a couple of inches above the knee or shorter and skip anything that's too full, lest your outfit start to like a figure skating costume.

The Best Pants for Ankle Boots

This one is nearly a no-brainer. Ankle boots work with any kind of pants. The advantage to wearing them over shoes or taller boots is that you get ankle coverage without the bulk of a knee-high boot.

If you want to tuck pants into ankle boots, they must be tight pants or at least those with straight legs. Wide-legged pants tucked into short boots create a very unflattering balloon effect.

Ankle Boots with Leggings or Tights

Cropped leggings don't work well with ankle boots. Long leggings or tights however, look great, assuming of course, that leggings look good on you in the first place. If they don't, pairing them with ankle boots isn't going to make the situation any better.

Clothes to Avoid Wearing with Ankle Boots

Here is the short list of the items you need to keep in the closet when you want to wear ankle boots.

  • Cropped Pants
  • Cropped Tights
  • Mid-Length Skirts with Bare Legs
  • Pencil Skirts
  • Shorts
  • Capris
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