Header Logo
Close this search box.

The Ultimate Guide On How To Wear Booties

Updated December 2019

how to wear booties
top: Zara, jeans: Joe’s, boots: Clarks

My clients are constantly asking me how to wear booties. My answer begins with the best jeans, and then I explain that not all booties can be paired with the same outfits. I have addressed some of these outfits on the blog already . . .

How To Tuck Jeans Into Booties

Booties With A Cotton Skirt

Booties With A Leather Skirt 

Pointed Toe Booties With A Midi Sweater Dress

How To Wear Socks With Booties


But there is so much more to discuss. In this post, I’ll elaborate on ankle boot outfit ideas I have already featured and explore even more outfits with booties. If you still have curiosities after reading my ultimate guide on how to wear booties, feel free to email me your questions.

Dresses To Wear With Ankle Boots

dress: Raga, boots: Stuart Weitzman

When wearing ankle boots with dresses, the best dresses tend to have an A-line skirt. This fuller line balances out the bulkiness of a bootie. The best booties to wear with dresses should have a heel over 1-inch and should have a fitted look. This means the boot doesn’t gape a lot or droop at your ankle.

Best Skinny Jeans For Ankle Boots

sweater: ASTR, jeans: Liverpool, boots: Paul Green

Good news! Basically all styles of ankle boots go with jeans. You just need the right jeans for each boot. Here are the best jeans to go with booties:

  1. Markie Skinny Crop by Joe’s Jeans
  2. Adriana Stretch Skinny Jeans by Mavi
  3. The Farrah High Rise Skinny Jeans by AG
  4. Maria High Waist Skinny Jeans by J Brand
  5. Good Legs High Rise Skinny Jeans by Good American (Size 0 – 24)

How To Cuff Your Skinny Jeans With Booties

top: Everlane, jeans: Liverpool, boots: Clarks

Cuffed jeans are the answer to most questions about how to wear booties, but you need to understand that not all jeans can be cuffed. When wearing booties with jeans, I see many clients trying to cuff jeans that are too long or too wide to cuff. You want to make sure your jeans are short enough for the perfect cuff, otherwise, the cuff will be too bulky. This is why I love to buy jeans that are already cuffed, like jeans 1-3 on the list above.

As for how to cuff them, you want to do 1-2 rolls. No more than that. The width of the roll is flexible, but ½ – 2 inches are all good widths. The rule of thumb is to roll however much you need in order to get less than an inch of skin between your bootie and your jean. You want the roll to almost sit on the bootie, but not quite.

Booties To Go With Leggings

top: Equipment, pants: Burberry (similar pants available, here), boots: Stuart Weitzman

When pairing leggings with ankle boots, skip any booties that have side openings like this Vince Camuto bootie, this Jeffrey Campbell bootie, and this Caslon bootie. You also want to avoid booties that cut at an angle like this Lucky Brand bootie. Instead wear slim fitting booties that go 1-2 inches above the ankle bone. Also, make sure your leggings are very fitted. Notice how mine are a little baggy at the ankles? You don’t want that.

Best Skirts To Wear With Booties

leather jacket: Rebecca Taylor, skirt: Rebecca Taylor, boots: Stuart Weitzman

Similar to dresses, you want a skirt with some volume or weight to it. If you want a tighter look, a leather skirt has the weight to pair well with a bootie. Otherwise, go for a fuller skirt like my J.Crew goodie, or an A-line look like my Vince skirt. This Vince item hits the mark on two levels by being A-line and leather.

top: Trouvé, skirt: Free People, boots: I.N.C

Booties That Don’t Go With Anything

Super flat booties with side cut-outs or pointed toes flatter next to no one. They look like shoes for an elf or the fox in Disney’s Robin Hood, but without the charm. I highly recommend that you avoid these shoes in particular:

  1. Lucky Brand Jamizia Boot
  2. Lucky Brand Felixah Bootie

Photos by Dayley Photography

Leave a note for Vanessa.

Leave a Reply

Your email address will not be published. Required fields are marked *


wardrobe stylist

Items selling out are my reader's biggest complaint. Sign up for my weekly updates so you get first dibs.

Are weekly emails too much? Sign up for the monthly round up and receive my personal five favorite recent purchases. In my professional opinion, you should sign up for both!

* indicates required
Please enter your e-mail address.
What updates do you want from me?

Sign up for my newsletter

* indicates required
Please enter your e-mail address.
What updates do you want from me?