10 Best Booties to Wear with Dresses This Fall

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I love wearing skirts or dresses with tights and booties. If you have a GREAT pair of booties, you can really dress up any outfit!

Pairing booties with dresses is an easy and classy outfit idea...if you know the right booties to wear!

This guide with the best booties to wear with dresses includes:

  • The Best Booties to Wear with Work Dresses and Skirts
  • The Best Booties to Wear with Dresses on a Date
  • The Cutest (and Affordable!) Leopard Print Booties to Pair with a Skirt
  • The Sexiest Lace-Up Booties to Wear with a Dress
  • The Best Booties for $50 with a Stable Heel

10 Best Booties to Wear with Dresses

The best booties to wear with dresses and skirts for fall 2020 by Very Easy Makeup
The Best Booties to Wear with Dresses and Skirts

Here are the 10 best booties to wear with dresses for spring, summer, fall, and winter. 

1. The Most COMFORTABLE Booties to Wear with Skirts –  Anne Klein Javen Ankle Bootie  

Anne Klein Javen Ankle Bootie_comfortable leather ankle bootie to wear with skirts
Anne Klein Ankle Bootie to Wear with Skirts

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I own these Anne Klein booties in black leather and brown suede.

I love pairing black booties with a short black skirt and an oversize sweater. It’s my favorite going-out outfit!

2. The Cutest Booties to Wear with a Dress on a Date – PiePieBuy Chelsea Pump Ankle Boots

Chelsea Pump Ankle Booties in light pink and peach and suede to wear on a date with a dress this fall
Cute Suede Ankle Booties with Bow in Light Pink/Peach

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These booties also look super cute with leggings!

the best suede booties to wear with leggings or dresses for fall fashion and fall outfits
Cute Suede Booties from Amazon to Wear with Leggings and Skinny Jeans

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3. Best Booties to Wear with Dresses with Buckle Strap – mysoft Zipper Bootie

brown mysoft zipper booties to wear with skirts with buckle strap
mysoft Zipper Bootie Chunky Stacked Heel Ankle Boots

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These booties also look great with skirts.
mysoft zipper booties in black to wear with skirts and dresses
Perfect for Wearing with Skirts and Dresses

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4. The Best Booties with a Low Heel – VEPOSE Ankle Boots

VEPOSE Women's Ankle Boots Low Heels Chunky Cutout Booties Perforated Western Shoes
VEPOSE Women's Ankle Boots

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5. The Best Booties to Wear with Dresses on a Date – White Snakeskin Booties  

Kathemoi Womens White Snakeskin Ankle Boots_Chunky Stacked Mid Heel Booties to wear with short dresses on a date
Sexy White Snakeskin Ankle Boots for Wearing with Dresses

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white snakeskin booties for fall to wear with skinny jeans or leggings online from Amazon to buy
White Snakeskin Ankle Boots with Jeans

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RELATED:

The Best Snakeskin Booties

6. Best Black and White Snakeskin Booties: WETKISS Snakeskin Booties

black and white snakeskin booties with comfortable heel by wetkiss to wear with mini skirts and tight jeans
Black and White Snakeskin Booties for Spring, Summer, Fall, or Winter!

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black and white snakeskin booties to wear with skinny jeans for fall and winter fall fashion outfits
Fashionable Black and White Snakeskin Booties (Under $50 Too!)

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7. The Most Classic Brown or Black Boots for Work Dresses – Sam Edelman Walden Booties

Sam Edelman black suede Walden bootie to wear with work skirts for fall
Sam Edelman Black Suede Walden Booties from Amazon

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Sam Edelman black leather Walden bootie with low heel to wear with skinny jeans
Sam Edelman Short Leather Boots with Skinny Jeans

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8. The Best Black Booties with Lace to Wear with Dresses – Chicago Chunk Heel Ankle Booties

sexy black booties and black boots to wear with dresses and ankle bootie to wear with skirts and tights
Leather Boots with Lace/Tie for Outfits with Skirts and Tights

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sexy lace and tie up boots with zipper and lace in light brown from Amazon
Brown Booties with Sexy Lace on Side and Zipper

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9. The Best Warm Booties to Wear with Tights and Dresses – Comfy Moda Winter Boots

Comfy Moda winter, lined, fur, dressy boots to wear in snow as ankle booties that work for work skirts and winter professional outfits
Warm Ankle Booties for Winter and Skirts

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10. The Best Leopard Print Booties to Pair with Dresses – Kenneth Cole Reaction Ankle Boot

the best leopard print ankle booties to wear with skirts and dresses by Kenneth Cole Reaction
Kenneth Cole Leopard Print Booties

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Outfits with Ankle Boots

Searching for a new dress or skirt to wear with your favorite pair of booties?

Here are outfit ideas on what to wear with ankle boots.

1. Tunic Dress with Booties

tunic dress with booties
tunic dress with booties

Get this Cute Outfit with Ankle Boots

Amoretu Women Summer Tunic Dress V Neck Casual Loose Flowy Swing Shift Dresses

 

2. Leopard Print Skirt with a Basic T-Shirt and Ankle Boots

Leopard print skirt to wear with booties for fall outfits
Maxi Leopard Print Skirt from Amazon

Copy this Fall Outfit with Ankle Boots

CHARTOU Womens Chic Elastic High Waisted A Line Leopard Print Pleated Shirring Midi-Long Skirt

3. Mini Skirt with Tights and Ankle Boots

mini skirt and ankle boots outfit
Perfect for Fall

Copy this Fall Outfit with Ankle Booties

Urban CoCo Women's Basic Versatile Stretchy Flared Casual Mini Skater Skirt

 

4. Off the Shoulder Sweater with Jeans and Ankle Boots

off shoulder sweater outfit with black jeans and ankle boots
Perfect for Fall Outfits

Copy this Outfit with Ankle Boots

Feiersi Women's Off Shoulder Sweater Long Sleeve Loose Pullover Knit Jumper

FAQs About Styling Booties with Dresses and Skirts

Styling booties with dresses and skirts is a fun and fashionable way to step up your fall wardrobe. Here are some FAQs you may have about how to rock this look:

What color dresses should I wear with black booties?

Black booties are versatile and can go with almost any dress color. However, pairing black booties with a neutral-colored dress like beige, gray, or navy blue can create a chic and classic look.

For a bolder choice, try a bright red or mustard-colored dress with your black booties for a pop of color.

What color dresses should I wear with brown booties?

Brown booties pair well with earthy tones, like olive green, burgundy, and mustard yellow. You can also try wearing them with a light blue or denim dress for more casual outfits.

Are leather booties or suede booties better for fall outfits?

Leather and suede booties are great for fall outfits but have different styles. Leather booties are more durable and can be dressed up or down, while suede booties have a softer look and are perfect for a cozy and comfortable outfit.

What is a bootie exactly?

A bootie is a type of shoe that covers the foot and ankle, but not the lower leg. Booties have short heels and can come in various materials like leather or suede.

Can I wear white booties in the fall?

Yes, you can! White booties can add a fresh and trendy touch to your fall outfits. Pair them with a neutral-colored dress or skirt, or try them with a bold print for a statement look.

Stitch Fix Inspired Booties for Fall Outfits

Stitch Fix Fall Booties
Image via Stitch Fix

Fall is the perfect time to swap out your flip-flops and sandals for cute booties!

You can dress up any fall outfit by adding a stylish pair of leather booties, leopard print booties, or suede booties.

If you love the Stitch Fix ankle booties featured in the Stitch Fix fall outfits, check out these similar booties online.

These booties look similar to the Stitch Fix ankle booties featured in the fall Stitch Fix outfits.

The only difference is that these booties cost MUCH less. And…they get great reviews from customers on Amazon!

1. Grey Suede Booties with Block Heel – Similar to Stitch Fix Grey Booties

DREAM PAIRS Women's Chunky Block Heel Ankle Booties

2. Snakeskin Booties for Stitch Fix Fall Outfits – Like the Stitch Fix Snakeskin Booties

Snakeskin booties with medium heel for fall 2020 booties and fall outfits
Snakeskin Short Ankle Booties

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3. Tan Suede Booties with Chunky Block Heel – Stylish Boots to Copy Stitch Fix Booties

high heel suede light tan booties to wear with long skirts
Suede Tan Booties to Wear with Skirts for Fall

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4. Leopard Print Ankle Booties – Affordable Booties Under $50 for Fall Outfits

leopard print booties to wear with jeans for fall 2020 booties and fall outfits
Leopard Print Booties to Wear with Jeans or Skirts

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More Fall Outfit Ideas

Cargo Pants Outfits 

Sweater Dress Outfit Ideas for Fall

Fall Outfits with Thigh High Boots

Explore All Fall Outfit Ideas

The best booties to wear with dresses and skirts
The Best Booties to Wear with Dresses
the best 10 booties to wear with dresses and skirts for fall by Very Easy Makeup, including leopard print booties, snakesekin booties, and suede booties
The 10 Best Booties to Wear with Dresses and Skirts from Amazon
The Best Booties to Wear with Dresses and Skirts for Fall by Very Easy Makeup
The Best Booties to Wear with Dresses

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