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!)

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Are you convinced to try the ankle bootie, now?