What to Wear with Ankle Boots

In all honesty, ankle boots are probably my least favorite style of women’s footwear.

It’s not that I dislike ankle boots for what they are, it’s more that I dislike how they’re worn — which is often in the most unflattering way possible.


I blame the media. Okay, that’s a cop out, and technically, I am part of the media, so I guess that statement needs a little clarification.

What I mean to say is that what we see on the runways and in fashion magazines does not always translate well for our own bodies and lives.

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? I’m so glad you asked. Here are a few of my favorite combinations.

Ankle Boots with Long Skirts

Whether they’re flat or heeled, ankle boots and long skirts are a classic combination. While I personally prefer to pair them with a long skirt that is on the fuller side, I’ve also seen ankle boots 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 — 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. But — and this is a big “but” — the only pants that work well tucked into ankle boots are very tight ones. Wide-legged pants tucked into short boots create a very unflattering balloon effect.

Ankle Boots with Leggings or Tights

I mentioned before that 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

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



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