Contrary to popular belief, your sneakers aren’t the only shoes with year-round appeal. If you’re preparing to pack away your “winter” boots, you’re also packing away one of the most versatile items in your wardrobe. In fact, boots are probably some of the only shoes that will ensure a seamless style transition between the seasons, especially booties, aka the low-maintenance little sister of thigh-high boots and heels. What makes them so appealing is their ability to somehow look casual and fancy at the same time. They’re chill enough for a dentist appointment and chic enough for a five-star restaurant. They also add height but still manage to be more comfortable than the alternative you have on standby. It shouldn’t make sense, but it does, and that’s why we love them.
Once you’ve seen that you can wear a pair of spring booties with jeans, dresses, jumpsuits, and even loungewear, you’ll never want to banish your boots to storage again. If you don’t already have a pair waiting in the wings for its star turn, step right this way. We’ve done the legwork for you and discovered the most stylish and comfortable boots for all of the spring outfits you have planned.
How We Found The Best Spring Ankle Boots
Our proprietary tool, an unbiased and smart algorithm, helped us compile this roundup by analyzing the kind of data shoppers depend on and trust. We’re talking social media buzz, expert recommendations, and editor reviews. Ahead, shop the best spring booties across a range of styles and prices.
Next up, check out the 10 Best Flat Boots. Opening image: freepeople.com
Top 10 Lists serve as unbiased shopping guides to the most trusted product recommendations on the internet. Products are scored and ranked using an algorithm backed by data consumers find most valuable when making a purchase. We are reader-supported and may earn a commission when you shop through our links.
Jeffrey Campbell Rosalee Bootie
WHY IT MADE THE LIST: The deep notches, stacked heels, and earth-toned color options give these boots a stylish Western flair.
PAIR WITH: Channel your inner rodeo star by wearing these with a pair of fitted jeans and a button-up blouse.
BP Brynne Bootie
WHY IT MADE THE LIST: The front of this boot extends to the top of the ankle, creating a super unique shape. The buttery-soft faux suede material also feels as luxurious as it looks.
PAIR WITH: Pull out your prettiest midi dress and hit the town in your comfiest strut.
Free People Charm Double V Ankle Boots
WHY IT MADE THE LIST: It doesn’t get much sleeker than leather and a pointed toe. Shoppers love the ease of this pull-on design and the cushioned insole for all-day comfort.
PAIR WITH: These booties were made for the spotlight, so make sure your skirt is short or your pants are cropped.
Free People We The Free Wesley Ankle Boots
WHY IT MADE THE LIST: The lived-in look of these western-inspired boots only adds to the unique appeal of its square toe and hand-stitched detailing.
PAIR WITH: Cropped pants or a short dress will leave room for you to show off the entire shoe.
Rag & Bone Rover Chelsea Boot
WHY IT MADE THE LIST: The slim ankle fit and modest heel make these boots an understated yet versatile fashion staple.
PAIR WITH: What won’t Rag & Bone’s Chelsea Boots look amazing with? Whether underneath a pair of flared pants, over a pair of tights, or with a mini dress, they’re bound to turn heads.
Treasure & Bond Emerson Chelsea Boot
WHY IT MADE THE LIST: The tall ankle cuff and angled platform heel are a unique combination that creates a sleek, minimalist silhouette.
PAIR WITH: Consider wearing these with a stylish dress or boyfriend jeans.
Dolce Vita Caster H2O Waterproof Block Heel Bootie
WHY IT MADE THE LIST: Rainy day or not, these platform boots are beyond chic. The lug sole provides sturdy traction on slippery surfaces, and the sandy shade contrasts beautifully against any of the shoe’s four color options.
PAIR WITH: Pound the wet pavement in a pair of sexy fitted jeans and a casual blazer.
Marc Fisher LTD. Alva Bootie
WHY IT MADE THE LIST: We’re obsessed with the front curve and tall block heel of this pull-on boot that screams sophistication.
PAIR WITH: Let ‘em know you mean business by wearing these boots with a pair of slacks or pencil skirt.
Mango Heel Leather Ankle Boot
WHY IT MADE THE LIST: The rectangular heel shape and unique leather-blend fabric separate this boot from the pack. The roomy ankle cuff also leaves room for pairing with socks or thick tights underneath.
PAIR WITH: The fabric moves with the shape of your foot, making it the perfect casual slip-on with a pair of shorts or oversized shirt.
Marc Fisher LTD. Yale Chelsea Boot
WHY IT MADE THE LIST: Maybe it’s the modern detailing on the pointed toe, or perhaps it’s the slim insole or pull-on style. There are plenty of reasons to love this boot, available in black leather and brown suede.
USER REVIEW: “I feel it is my civic duty to tell you this. These are the most comfortable shoes I have ever owned. They are like slippers you are allowed to wear in public. Very fashionable, socially-acceptable slippers. I bought these shoes on a whim. I've always believed I couldn't wear booties like this because of my short stature (I'm 5'2"). I was very skeptical when I was encouraged to try these on, but somehow they worked!”