How to Wear Ankle Booties with Dresses

Booties aren’t just for wearing with jeans or leggings, we all know they’re great with dresses and skirts too! And because it’s fall season, we thought we’d do a quick how-to guide on wearing ankle boots with dresses just in case some of you ladies need the tips.

So how do you wear booties with frocks? Well, it’s really just a matter of height and proportion. But before you start putting the combo together, there are a few things you need to consider and remember:

1. Understand the Ankle Boot and Consider Your Height

Do understand that ankle-high booties end at the ankles or above it. And because of this, they can cut the length of your legs making you look shorter than you are. Which is why if you’re petite, wearing ankle booties can be tricky. If you’re tall and leggy however, this wouldn’t be a problem since you can afford to lose a few inches.

Elisabeth Glittered Bootie in Black, $44.95

2.Wear the Right Dress Length

Generally speaking (and most especially for petite or short women), ankle-high boots work best with short frocks when worn alone (no tights). And by short we mean mini dresses. If you want to go a little longer, three inches above the knee would be the max you can go. Simply put, the shorter the hemline, the taller (and sexier) you will look. Do the opposite (knee length and tea length) and you will look shorter. Unless of course, if you go all-out on the length and wear a maxi.

Mini Dresses + Ankle Boots = Perfect Mix

left to right:

Look #1: 3.1 Phillip Lim Peek-a-Boo Lace Dress, $475 / Phillip Lim Peggy Ankle Booties, $695

Look #2: Heather Double Mini Dress, $128 / Rag & Bone Classic Newbury Booties, $495

Look #3: Clu Sweater Dress with Pleats, $362 / See by Chloe Clog Booties, $415

3. Work Around So You Can Wear Any Dress Length

Ok, just because we said ankle boots work best with mini dresses doesn’t mean you can’t wear longer ones. There are simple tricks you can do to still be able to wear any dress length you want. Here are a couple:

  • Go with nude or neutral boots – Yes, to be able to wear that knee length frock (or even tea length), go with a pair that matches your skin color. That way, you won’t look like your legs were cut in half twice (remember, a hemline is a horizontal line that cuts across your legs the same way ankle-high boots cut across).

Nude or Neutral Booties = Best for Knee or Tea Length Frocks

Look #1: Thakoon Longsleeve Wrap Dress, $690 / Maison Martin Margiela Plexi Covered Wedge Bootie, $1295

Look #2: Nation LTD Laguna Nigel Dress, $150 / Joie Lennon Booties, $295

  • Wear same color tights - - The idea behind this is very similar to the first point, which is simply to create the illusion of continuity and zero (eye) distraction to avoid looking short. The tights and boots will blend together and make you appear tall enough to accommodate say, a tea length hemline.

4. Wear It with Confidence

At the end of the day however, these guidelines are just, well, guidelines. What’s important is you feel good in what you’re wearing. Confidence is the key. You’ve got to have the spunk to pull off the booties and dress combo; it’s practically the first step to looking fabulous.

For fresh ankle bootie styles perfect for the holiday season, check this post from our sister site Your Next Shoes. Enjoy dressing up!

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