How to Wear An Ankle Bootie

I was late to the ankle bootie party. When they first came into fashion a few years ago, I thought they were odd looking and I had no idea how to wear them in my regular work-at-home mom life.

Last fall, I finally came around and bought my first pair.

As with most new-to-me trends, it takes a few times wearing an outfit that feels awkward and forced before it becomes comfortable. The first few times I wore these booties, I didn’t know quite how to wear them. Do you cuff your jeans? Or double roll them? What kind of socks? Can you wear them with a dress? Bare legs or with tights?  I really wasn’t sure.

If you look around on pinterest or in magazines, you’ll find countless examples of bootie-wearers. Some outfits are great and mimic-able for the everyday; many are not.

So since I’m a busy mama who likes to look cute, but doesn’t work too hard at putting together fancy or unrealistic outfits, I thought I’d share with you my thoughts on how to wear an ankle bootie. If you haven’t taken the bootie plunge, perhaps these simple suggestions will win you over.

WITH SKINNY JEANS

This is the way I wear my booties most often. I appreciate that the chunkier boot adds balance to a skinny jean that tapers down (balancing out the hip/thigh region). I find booties are often times more comfortable and casual looking than skinnies paired with tall boots (although still a look I like).

To wear, cuff once or roll twice to expose just a bit of your ankle.

With slightly taller ankle boots, there’s no need to cuff – just tuck your jeans in like you would tall boots. This will elongate the line of your legs which is always a plus.

SOURCES:  skinny jeans / old navy liner socks / toms wedge booties

WITH BOOTCUT JEANS

Hooray for bootcut and flare jeans coming back. I suppose they never fully went away, but we’re seeing many more outfits and options with bootcut jeans than we did even a year ago.

I remember wearing ankle boots in high school with jeans, and this is really no different now. Add height with a heel, or go with flats but just make sure the hem of your jeans hit the base of the shoe. Steer clear of the high-waters.

SOURCES:  bootcut jeans / gap trouser socks / ankle booties

WITH A DRESS OR SKIRT

Admittedly it has taken me a while to feel comfortable wearing ankle booties with a dress or skirt. Now that I’ve crossed that bridge, I find booties to be a very practical choice for the fall and a great (more casual) alternative to heels.

Wear bare-legged, with ankle socks (a bit more fashion-forward and probably just for the younger crowd) or opaque tights that match your booties to make your legs look extra long. 

SOURCES:  dress / opaque tights / wedge booties