• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Skip to footer
Cleo Madison
  • Shop Modest Clothing
  • Styling Tips
  • Modesty
    • Facebook
    • Instagram
    • Pinterest
    • Twitter
    • YouTube

How To Style Booties (Even When You’re Scared You Won’t Pull Them Off)

Disclosure: Some of the links below are affiliate links. At no cost to you, I will earn a commission if you click through and make a purchase. 

If you’ve ever been afraid to wear booties and not pull them off, then you’ve come to the right place!

This blog post will show you several different ways of how to style booties and give you so many outfit ideas.

Booties are also known as ankle boots. They are boots with a short shaft that does not go very high up on your calf.

Booties look super cute with skinny jeans, straight leg jeans, skirts, or dresses. Ankle boots are so versatile because you can wear them casually or to work and church. Fall is the best time of the year for wearing a cute ankle bootie, but they’re great year round.

This post will you give a lot of outfit inspiration for your next booties outfit! These outfits are cute, trendy, cozy, and chic.

There are also different types of booties being worn in this outfit guide. You’ll see a pointed toe bootie, heeled ankle boots, and some outfits with a flat ankle boot.

How To Style Booties Outfit #1 – With Overalls

See how Alexa Neff Bagshaw styles her black booties for fall.

Alexa Bagshaw is wearing a really fun fall outfit. She styled her black heeled ankle booties with rust colored skinny overalls and a black and white striped t-shirt. We love how there is a little gap between the end of her overalls and the top of her booties.

Shop this look:

  • Similar booties here
  • Similar overalls here
  • Similar t-shirt here

Outfit #2 – With A Utility Jacket

Hailey Devine's fall outfit with booties

Hailey Devine from Somewhere Devine is wearing low-cut booties that have little straps across the top. She is wearing them with a black skinny jean, a chambray button down top, an olive green jacket, and a green neck scarf. This is such a cute example of how to wear ankle boots.

Shop this look:

  • Similar booties here
  • Similar jacket here
  • Similar jeans here
  • Similar shirt here
  • Similar neck scarf here

Related Content: 19 Modest Fall Dresses You Should Definitely Buy

Outfit #3 – With A Cardigan

fall outfit featuring pink wifey shirt, black hat, blue skinny jeans and black booties

This is how I styled fall booties on my lifestyle personal blog. I’m wearing black booties with little cutouts. I paired them with light colored skinny jeans, a mauve graphic tee that says “Wifey”, an over sized cardigan, and a black hat. I rolled my jeans up about an inch and a half to create a little bit of a gap between the pair of jeans and booties.

Shop this look:

  • Similar booties here
  • Similar tee here
  • Similar cardigan here
  • Similar hat here
  • Similar jeans here

Outfit #4 – With Skinny Jeans

Outfit styling with brown booties

Jenn, who blogs on Mrs. Casual is wearing brown ankle boots with distressed jeans, a black and white striped v-neck t-shirt, a long camel colored cardigan, and a leopard purse. Her jeans are slightly tucked into her booties.

Shop this look:

  • Similar boots here
  • Similar tee here
  • Similar cardigan here
  • Similar jeans here
  • Similar purse here

Outfit #5 – With A Skirt

Elizabeth styling an outfit featuring a long cardigan, black, skirt and brown booties

Happily Elizabeth has on a really comfy and casual outfit with her ankle booties. Her booties are a light tan color and she is wearing them with a black jersey skirt, a white t-shirt that has a black collar, and a long light pink cardigan. You could also wear this outfit with a pencil skirt.

Shop this look:

  • Similar booties here
  • Similar skirt here
  • Similar cardigan here

Outfit #6 – With A Sweater

See how Amy Jackson styled her fall booties

Fashion Jackson has on a very chic, fall look. She is wearing tan ankle boots with a heel. She has them on with distressed medium wash jeans, a white, loose sweater, and a tan bag. Her jeans end right about where her boots start.

Shop this look:

  • Similar boots here
  • Similar sweater here
  • Similar jeans here

Outfit #7 – With A Leather Jacket

See how Emily Gemma styled her black booties

Emily from The Sweetest Thing blog is wearing such a fun fall outfit. She has on black leather ankle booties with grey jeans, a white sweater, a black leather jacket, and a leather purse. We love how she tied together the booties with her jacket. Her jeans tuck into her boots a little.

Shop this look:

  • Similar booties here
  • Similar jeans here
  • Similar sweater here
  • Similar jacket here
  • Similar purse here

Outfit #8 – Roll Your Jeans Up A Little

Amy from Straight A Style Blog styling her tan booties

We can’t get enough of this outfit that Amy from Straight A Style is wearing. She has on camel colored ankle boots with distressed jeans that she rolled up, a nice black top, a camel colored hat, and a camel colored purse. We love all the fall vibes of this outfit.

Shop this look:

  • Similar booties here
  • Similar hat here
  • Similar purse here
  • Similar jeans here

Related Content: 19 Easy Modest Halloween Costumes You’ll Love

Outfit #9

Kristin Rose Davis from Wild One Forever styling jeans, booties, and fall sweater.

Kristin Rose Davis of Wild One Forever is wearing such a comfortable fall outfit. Her booties are tan colored, perforated, and have pointy toes. She is wearing the pointed toe boot with grey jeans, an over sized maroon sweater, a purse, and some silver jewelry. This is a really fun way to style ankle boots.

Shop this look:

  • Similar booties here
  • Similar sweater here
  • Similar jeans here

Outfit #10

Jenica Parcell from A Slice of Style styling with gray booties.

Jenica from A Slice of Style is wearing grey booties that are so fun. They are low-cut and dip down where the ankles are. She is wearing them with blue jeans and a light pink sweater.

Shop this look:

  • Similar booties here
  • Similar sweater here
  • Similar skinny jeans here

Outfit #11

Cristina Gamarnik from OC Mom Lifestyle styles her gray booties with jeans and a sweater,

Cristina from OC Mom Lifestyle is giving us all the fall vibes with her outfit. She has light tan booties with dark distressed jeans, a rust colored sweater, and a tan purse. She roller her jeans up just a tiny bit so that they sit above the boot.

Shop this look:

  • Similar booties here
  • Similar sweater here
  • Similar skinny jeans here

Outfit #12 – With A Dress

Style brown booties with a navy and white plaid dress

Kinsey is wearing brown ankle boots with her outfit. We love how she styled her booties with a dress rather than with jeans. She is wearing a navy and white gingham dress with white tights, a red neck tie, and a brown hat.

Shop this look:

  • Similar ankle boots here
  • Similar tights here
  • Similar hat here
  • Similar neck scarf here

Outfit #13 – With A Vest

See how One Little Momma styles her brown booties.

Kilee Nickels from One Little Mama styled her brown, pointy ankle boots with a charcoal dress, a fur vest, a brown leather purse and some jewelry. This is a great look for early fall when it’s not too cold yet since her dress has short sleeves. 

Shop this look:

  • Similar ankle boots here
  • Similar dress here
  • Similar vest here

Outfit #14

Kailee Wright styles her brown booties with a long cardigan and a light gray maternity dress.

Kailee Wright is always someone to look to for fashion inspo. Her maternity fashion in the fall is so effortless and cute. She styled her brown booties with a light grey knee length dress and a very long burnt orange cardigan.

Shop this look:

  • Similar booties here
  • Similar dress here
  • Similar cardigan here

Outfit #15 – All Black

Style leopard booties the way Taylor Morgan from Little Blond Book does.

Taylor, who blogs on Little Blonde Book, is wearing leopard print booties. She is wearing distressed black jeans that she rolled up a little to look more like cropped jeans, a black 3/4 length shirt, a knit vest, a black hat and a brown purse. We love this look for fall.

Shop this look:

  • Similar leopard booties here
  • Similar jeans here
  • Similar hat here

Pin this image to save this post for later!

how to style booties

As an Amazon Associate I earn from qualifying purchases.

Subscribe

to get blog updates.

Previous Post: « 15 Bermuda Shorts Outfit Ideas You’ll Love
Next Post: How To Style Jean Jackets: 12 Outfit Ideas To Copy »

Primary Sidebar

Welcome

Elizabeth Morgan who owns Cleo Madison

I'm Liz, a modest fashion blogger and twin momma. It's my mission to help you find modest clothing for every occasion! Read More

Join The Newsletter!

Sign up to be notified of new posts!

Footer

COPYRIGHT © 2022 CLEO MADISON

About • Contact • Privacy Policy • Accessibility • Terms & Conditions