How To Wear Your Ankle Booties

See our Stylist’s favorite ways to wear ankle booties!




  1. They go with everything. Seriously, ankle booties go with every outfit, every season.
  2. Highlight your hems. An unfinished hem is the denim trend du jour and what better way to show it off than with a pair of ankle booties?
  3. Add some color. Look at what makes up the foundational colors of your wardrobe, then pick your boot hue based off of your palette.
  4. Choose your heel height. Whether it’s a seemingly flat Chelsea boot or sky high stiletto boots, you can have a pair for every occasion.

How to Wear Ankle Booties

Wear Your Booties With A Boho Flair

Bohemian dresses + booties are a style match made in heaven. And, it’s only natural! In terms of footwear, booties are easy and accessible which mirrors the nature of the boho-girl with her easygoing nature and insouciant nonchalance. Pair a chunky, stacked heel with a feminine dress with boho details to get the look in two steps.


  • Textured Cardigan: Add cozy texture to your look with a textured cardigan. Pefect for layering up in chilly weather.
  • Feminine Dress: Grab a flirty dress (maybe one you loved from summer), and take it into fall.
  • Stacked-Heel Bootie: We can’t wait to rock colored booties this fall!

How to Wear Ankle Booties

Style Your Booties For On-The-Go

In a time bind? Here’s how to create the perfect outfit in less than five minutes. Step 1: Reach for your coziest fall toned sweater. Step 2: Add on-trend denim (like ones with a button-fly!) Step 3: Slip into a pair of colored, moto-inspired ankle boots. Step 4: Run out the door and get your day started.  


  • Fall Toned Sweater: Be one with nature! Let your style palette reflect warm fall tones.
  • Skinny Jeans: Always a classic, your leg lengthening skinny jeans now with button fly detail!
  • Moto Bootie: So comfy, super chic, work and play-appropriate.

How to Wear Ankle Booties

Style Your Booties For City-Living

When you live in a compact city, you never know who you might run into (an ex, your boss?). Keep it chic with dark wash denim and a crisp white button-down that can take you from a meeting with your manager to happy hour. Go for a classic block heel booties to help you weave through those crowded city streets.


  • Cargo Jacket: Our favorite neutral staple for any outfit!
  • Dark Denim: Slim, polished and classic. Need we say more?
  • Chelsea Bootie: Show off a little skin (on your ankles!) with fall’s favorite bootie.

How to Wear Ankle Booties

Style Your Booties Simply

Want all style with no fuss? Go minimal! Try out a pair of sky-high stiletto ankle booties for a leg-lengthening look. If you have to stay ready for anything (like running after the kiddos), slip into black Chelsea ankle boots instead. They have elastic on the side which means you can slip them on in seconds.


  • Oversized Layers: Not just your old hoodie, oversized can be totally chic and flattering!
  • Sleek Leggings: Add some streamlined structure to your layers.
  • Stiletto Bootie: Turn up the heat! We love stiletto booties for a night out.

What do you think? Tell us in the comments below!

The post How To Wear Your Ankle Booties appeared first on Stitch Fix Style.

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