How to Rock Ankle Booties


ankle bootiesBoots are one of my favorite things to wear on my feet. They keep my feet toasty warm and can make any outfit chic no matter what you’re wearing. During the fall I especially love ankle booties, because they’re even more versatile than high boots. If you are wondering how to tackle the trendy ankle bootie obsession, follow this easy stylin’ tips on how to rock ankle booties.

The Basics

Before I delve into the plethora of ways you can wear fabulous ankle booties. Let’s first cover some ground rules. The first rule in rocking ankle booties is to get yourself a pair of no-show socks. I love these ones and you can find them at Target, CVS, or my favorite “store” Amazon. Another helpful hint is to pair your booties with clothes where you can show them off…aka don’t wear them with flare pants. Booties are styled best with dresses, leggings, and the ever-popular mommy fav jeggings.

The Summer Dress turned Fall Look

Go to your closet and grab a super comfortable summer dress. Add a simple cardigan or jacket and you have yourself the perfect fall look. This is outfit is awesome for the days that start off kind of chilly and have you sweating by the afternoon. I also like how I can extend my summer wardrobe and get some more use out of my seasonal dresses.

Soccer Ready

As a busy working mom the last thing I want to wear on the weekends are “work clothes,” so I am constantly reaching for my trusty leggings. But look at this…pair your elastic waist leggings with a cute pair of ankle booties and you got yourself a fashion-forward outfit that it super comfy to “boot” (mom jokes are awesome). The fun leopard print on these booties is sure to help you strike up a conversation with other mommas on the side of the turf field or the waiting room in a Dance studio.

Office Glam

Ankle booties are also a great choice for the office. I love to pair my neutral booties with a cozy sweater dress. Grab a colorful scarf and you have a lovely outfit that can take you from meeting to meeting. 

Night Out on the Town

ankle boots

Whether you are off to grab some drinks with the ladies or Grandma is visiting and you scored an “adult only” evening with your partner, booties are a great choice for the perfect fun evening outfit. I love the simplicity of pairing booties with a quality pair of skinny jeans. Add a simple black tank and some fun earrings and you are ready for concerts, bars, movies, and more.

My Go to Airport Outfit

ankle boots

If nothing else ladies, PLEASE, PLEASE follow this amazing mom hack. Wear ankle booties on airplanes. I have worn this exact outfit on three trips last year and I never regretted it once. Ankle booties allow you to take your shoes on and off with ease while balancing a toddler on your hip and holding the hand of your squirming preschooler. Added bonus the booties are great for all the airport walking (aka sprinting when you are late) and are the perfect choice to step up your outfit game when you arrive at your destination. Here I wore my distressed jeans and because I am petite I had to roll the hem slightly to show off the shoes.

Don’t Forget to Have Fun

This outfit is way outside my fashion comfort zone, but I absolutely loved wearing it. I adore the feminine flowiness of the dress and the ankle booties give the ensemble a little more versatility. This outfit would be an outstanding choice for a brunch, baby shower, or day date with your love. I think one of the most important aspects of fashion is wearing an outfit with confidence.

How do you rock ankle booties? 

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Nikki has called wonderful Fairfield County her home, her entire life. Growing up on a campus of a private school in Greenwich, CT Nikki swore to her educator parents that she would never be a teacher. Well life has a way of repeating itself and now Nikki and her amazingly supportive husband are happily working at a different independent school in Greenwich. A recovering “type a” perfectionist she is learning to let go of her color coding, alphabetizing ways and embrace the mess. Helping her enjoy life’s everyday messes are her two precocious girls Sofie (11/15/11) and Keira (9/7/13). Nikki loves all things mommy cliché including but not limited to walks on the beach, running, reality TV, organizing closets, wine, chocolate and having her kids help her out in the kitchen.


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