Five Ways to Wear Ankle Boots

Five Ways to Wear Ankle Boots

Want to know what the most burning question has been on GYPO readers’ lips lately?  I’ll bet you can guess from the title.

How the heck do you wear ankle boots?!?

They’re cute, no doubt, but these little buggers can be a bit tricky to style.  When I bought my first pair, they sat in the closet for almost an entire season with no wear.  When I finally got up the nerve to pair them with some jeans, I was hooked and eager to find other ways to wear them.  Before long, I was experimenting with all kinds of ways to pair them up and ready to add to my ankle boot collection.

Here are five of my favorite ways to pair up ankle boots.

1.  Ankle Boots with Ankle Jeans

Well, duh, that just makes sense, right?  Ankle jeans were practically made for ankle boots and retailers are getting on the bandwagon with this trend.  There’s hardly a store you’ll walk into this fall that doesn’t have some cute ankle jeans that are the perfect length to fall just above your ankle boots.

Embellished Sweatshirt Jeans Full 2

2.  Ankle Boots with Cuffed Skinny Jeans

If your skinny jeans are longer than ankle length, just cuff them right above the top of your boot.  Easy peasy!


3.  Ankle Boots with Boyfriend Jeans

Take a cue from Rosie Huntingdon-Whiteley and pair your slouchy boyfriend jeans with a cute pair of ankle boots.  Throw on a t-shirt, scarf and jacket and you’re instantly chic for fall.

Rosie Huntington-Whiteley. I'm going to have to try the boyfriend jeans with booties style.

Or try the trend with a military jacket and white tee.

Fall outfit ideas. Military jacket. White tee. Nude scarf. Cuff jeans. Cognac suede ankle boots. Rachel Bilson in the Harrow Boot

4.  Ankle Boots With Socks

Scrunch some wool socks above your ankle boots when pairing them with skinny jeans or leggings for a cute and cozy look.


5.  Ankle Boots With Dresses/Skirts

Swap out your typical heels and try a pair of tights with ankle boots this fall.  It’s a modern look that’s sure to instantly update your outfit.

10 Ways to Wear Ankle Boots | Monochromatic | A monochromatic look is a great way to wear those taller ankle boots...a pair of black tights and a black pencil skirt creates a sleek long black line that makes it so the height of the boot is irrelevant.  Tip #8. Try a fun patterned top to offset the monochromatic bottom! Tip #9. Try brown tights with brown boots, gray with gray, or mustard with your light brown boots! Shopping Options

[Ava Ankle Boot]

[Hartley Ankle Boot]

[Lace Up Bootie]

[Suede Ankle Strap Boot]

[Whysper Ankle Boot]

[Suede Low Heel Ankle Boot]

[Vince Camuto Ankle Boot]

It’s Your Turn:  What’s your favorite way to wear ankle boots?  Tell us in the comments.

Stay tuned for an announcement about the Fall Style Challenge on Monday.

Fall FB Cover Graphic White Learn More

Getting my pretty on with The Pleated PoppyOne Stylish Mom and Erika and Andrea.