How to Wear Ankle Booties

Ankle booties: you either love them or you hate them. If you’re the latter, you’ve likely made the following excuses as to why you absolutely cannot do the “ankle boot thing.” Such as:

They look weird with all of my skirts.
They look frumpy tucked into my pantswait, do you tuck them into your pants?
I can’t pull off the rolled denim pants thingis “cuffing” the same as “rolling”? I can’t keep up.
They look super awkward with my office slacks. I can’t be that girl that tries too hard at work.
They make my legs look like stumps.

We’ve heard it all before (and we’ve even thought a few ourselves!) but we’re here to dispel those rumors. Today we want you to know how perfect the ankle boot can be in just about any fashion situation. So, we enlisted the help of one of the most stylish Everygirls we know—Jess Kirby, of Prosecco and Plaid, to show us how it’s done.



“My favorite kind of weekend is casual and comfortable,” Jess says. “Since we live in town, we can walk pretty much everywhere, so I love to take a stroll to brunch, walk along the water and take in the scenery, or go thrift shopping. An ankle boot with a casual, low heel is my go-to for weekendsthey give that added edge for an easy, effortlessly chic vibe.”

How to style: 

  • Wear a pair in a light color—like these, in white. Unexpected, and the perfect color to transition into spring.
  • Go for a rounded toe, which keeps them casual and comfortable, with a small heel, which adds a bit of height to makes them extra flattering.
  • Style with boyfriend jeans, and roll the bottoms so a little ankle shows, which elongates your legs. (Tip: Make sure the legs of your boyfriend jeans aren’t too wide, or your look will end up looking goucho-chic, which might not be what you’re going for!)

Shop this look: Gray Coat (on sale), SweaterStriped Button DownJeansAnkle boots, Leopard bagEarringsLipstick (in Schiap), Sunglasses



“There’s nothing better than a cozy, romantic date night!” says Jess. “When the only walking I have to do is from the car to the restaurant, I pull out my highest heels! I’ve had these burgundy booties for two years now and I really think they’re a timeless style. I’ve worn them with everything from ripped jeans to trousers and I particularly love them with this lace dress. Since it’s still chilly winter here in New England, I layered a warm turtleneck sweater over the dress. The burgundy of the bootie gives the outfit a nice pop of color.” 

How to style: 

  • Pointed toes make the look more feminine, and dressed up.
  • High heels are perfect for the occasion (not much walking necessary!) and they add height, to elongate the legs. 
  • Pairing booties with a feminine skirt adds another dimension to a feminine outfit.
  • Look for a pair in a dark wine color, which is more interesting alternative to black and brown, and is neutral enough to pair well with just about any color.
  • For the most flattering silhouette, cut of the boot should come just above the ankle, and be significantly wider than your legs to avoid looking “stumpy”.

Shop this look: Sweater (on sale), Ankle boots (on sale), Lace pencil skirt, Lipstick (in Red Lizard), WatchBracelet



“When I have a day of client meetings I need to be comfortable,” Jess says. “The last thing I want to be thinking about is my feet aching, or worrying that I’ll fall in sky-high heels in front of a client. (How embarrassing!) A flat, pointed-toe, patent leather bootie is my go-to for days when I’m running around to meetings and appointments, and is a much more stylish alternative to a ballet flat! I love them with these wool trousers and slouchy sweater, but they’d look great with a shift dress or midi skirt too.” 

How to style: 

  • Look for a low to flat heel, which is the most practical for days when you’re running in and out of the office, or to and from multiple meetings. Waddling into the conference room with hurt feet is never a great way to make an impression.
  • Pointed, patent leather booties are sleek and sophisticated, and balances out the casual factor of the flat boots.
  • Pair your booties with trousers for an “office chic” look, but make sure they’re slim cut, and end above the ankle. There should be a tiny bit of room between the boots and your pants. If they are cut too long, you can always roll them. (Refer to look #1!)
  • Finish with a slouchy sweater and pea coat to keep you warm and toasty.

Shop this look: Silk ShirtTrousersBootiesSweater (on sale), Coat, Lipstick Pencil (in Dragon Girl), Sunglasses (splurge!)

Follow Jess on Social: Instagram // Facebook // Twitter // Blog

Are you convinced to try the ankle bootie, now?

  • I don’t know. I still don’t like the look. I just think they make pants look too short. With the skirt, fine, but pants? I won’t.

    • If the rolled look isn’t your thing, you could always pair them with a pair of snug skinnies, then they’ll tuck perfectly into your boots, no rolling needed 😉

  • lwh13

    I love the first two looks – but can’t get down with the patent just yet. Being cut above the ankle is definitely crucial for me – and confidence!

    Warm Regards,

  • I really do want to love it; but every time I try ankle booties on I feel like they make my legs look a little stumpy. I need to find some that don’t cut off straight across maybe.

    Sunday Brunch

  • Lane

    A piece like this on how to wear tights and/or leggings would be greatly appreciated! I try and fail every time!

    • Hi Lane! We do have a piece like this on leggings 🙂 You can find it here!

  • Michelle

    I’ve been waiting for a post on how to wear ankle boots! I’ve been wanting to get a pair and this definitely helps with figuring out what to wear them with!

  • mrscogswell

    I feel like her skirt actually needs to be shorter…this look gives her legs weir proportions and actually makes her look shorter. Also, the booties with the suit look inappropriate, not fashion forward. It looks like you were trying to take a risk, but that risk turned out sloppy. Love them with jeans and leggings!

  • Lizzy

    two words: Leather pants

  • I really enjoyed reading and looking at your images, they are well taken and self explanatory, There is one question though if I may ask, Is it always necessary to show a little bit of skin when wearing ankle boots? I mean can’t I just wear it over the jeans?