The 17 Best Ankle Boots To Wear With Skinny Jeans

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While ankle boots are a versatile addition to your wardrobe, they pair especially well with a pair of skinny jeans — and there are so many boots to choose from on Amazon. Whether you prefer high heels, low heels, platforms, or wedges, the best ankle boots to wear with skinny jeans are perfectly suited to your style and come in a variety of colors and prints.

For example, if you’re looking for a great everyday shoe, a pair of classic black ankle booties will go with everything. Or, opt for lighter neutral shades such as brown, gray, and sand. But if you want your shoes to stand out and pop, consider leopard print, snakeskin, or bold red boots.

Along with heel height, think about how the shoe’s silhouette will complement your skinny jeans. A mod ‘60s-style boot creates a super sleek look, while chunky lug soles and combat boots can create balance with form-fitting jeans and add a touch of cool.

Whatever your style preference, you’re sure to find a pair (or two) of ankle boots that you’ll love wearing with jeans — and pretty much everything else in your closet. Plus, most of the boots below are super comfortable enough to walk in them all day long with ease.

These Cut-Out Boots With Chunky Heels

These stylish ankle boots will look amazing with any pair of skinny jeans, and they come in over 20 styles and colors, including classic black, brown, leopard, and snakeskin. The faux leather boots have pointed toes and stacked heels, and some styles — like the pair featured here — have back zippers for easy on and off.

One rave review: “Love, love [these] boots! I can't believe how comfortable they are! I can walk on these all day long.”

  • Available sizes: 5 — 11
  • Available colors and styles: 22
A Chunky Chelsea Boot For Less Than $30

To balance out the streamlined silhouette of skinny jeans, pair them with these chunky Chelsea boots. Made from soft suede with flexible gore panels, these boots are easy to pull on and super comfy. Plus, there are seven versatile colors to choose from, including gray, black, and brown.

One rave review: “They’re comfortable, easy to walk in and give a great amount of height without feeling like heels. They go great with so many different things, from skinny jeans to dresses to shorts these look good with anything. These are one of my favorite pairs of shoes, I’ve worn them all winter long and am looking forward to finding ways to style them this summer.”

  • Available sizes: 5 — 11
  • Available colors: 7
These Comfy Boots With Shock Absorption For All-Day Wear

Featuring cushioned insoles with arch support, these lightweight ankle boots are designed for all-day comfort. The faux leather slip-on boots have twin gore panels and flexible soles for comfort, and they offer shock absorption to help reduce pressure and fatigue. In addition to this smooth black leather style, you can also choose from animal print and various shades in suede.

One rave review: “This is the comfiest and cutest shoe I've ever owned! It's perfect for those who need a little bit of extra support and it is good for people who are on their feet all day (I work retail!). Highly recommend!!”

  • Available sizes: 6 — 11
  • Available colors and styles: 5
A Strappy Bootie For Less Than $35

These highly rated ankle boots are another popular pick with Amazon shoppers, and they’re budget-friendly, too. The low-heel, faux suede boots feature a stylishly strap design, and you can also opt for cutout and classic boot styles in versatile shades of brown, black, and gray.

One rave review: “I absolutely love these shoes. They are pretty comfy and super cute with dresses and skinny jeans/leggings.”

  • Available sizes: 5.5 — 11
  • Available colors and styles: 8
Some Soft Suede Ankle Boots

Made from 100% microsuede in rich cognac, these minimalist ankle boots are super stylish — and they’ve garnered almost 1,000 perfect five-star ratings. The faux leather boots also have padded memory foam insoles for comfort and an inside zipper for easy on and off. In addition to this suede style, the boots are also available in smooth black faux leather.

One rave review: “I love the chunky heel. Very easy to walk on. I had these on all day (9+ hours) and they are very comfortable. You're feet don't get tired or ache at the end of the day. I love the noise the heel makes. When you walk, it makes the classic "click clack" sound.”

  • Available sizes: 5 — 14 (including wide sizes)
  • Available colors and styles: 2
These Dr. Martens Chelsea Boots

These Dr. Martens ankle boots are made from 100% leather and durable enough to last through years of wear. Reviewers praise the high quality of these boots, with several mentioning that almost no break-in period is required — just pair them with your favorite skinny jeans (or any outfit, really) and you’re good to go for a touch of effortless cool.

One rave review: “They maybe the most comfortable boots I've ever owned starting the with first time I put them on. The pebbled leather is soft and flexible with no need for break in. The ankles are snug enough so that slim jeans can cover them although they also look great with skinny jeans stacked on top of them or cuffed.”

  • Available sizes: 5 — 11
  • Available colors: 1
A Pointed Bootie With A Kitten Heel

Not only are these kitten heel booties comfortable to walk in all day, but they’re also very much on trend. The faux leather pointed-toe boots are available in a range of styles and colors, including black, white, and leopard print, and feature padded insoles and side zippers for comfort and ease.

One rave review: “These are great, stylish and comfortable. They look great with a skirt or pants.”

  • Available sizes: 5 — 10
  • Available colors and styles: 9
These Rugged Cowboy Boots

If you’re looking for a shoe that’s a bit more rugged, these distressed cowboy boots have a lived-in look that’s effortlessly cool, and their ankle height makes them perfect for skinny jeans. The 100% leather boots have stacked heels and embellished straps with western style. Choose from black or white.

One rave review: “I love these booties! Great quality, cute on the feet, and comfortable.”

  • Available sizes: 5.5 — 10
  • Available colors: 2
A Waterproof Chelsea Boot With Nonslip Soles

Rainy days are no match for these waterproof ankle boots, which are made from faux leather and have chunky, nonslip rubber soles that cushion your feet and provide shock absorption. The boots also have elastic side panels for easy on and off. There are six versatile colors to choose from, including gray, black, and white.

One rave review: “They wear great, easy to get on and off, i can wear them all day with no problems. i got the black ones and they look really great with [leggings] or skinny jeans.”

  • Available sizes: 5 — 9
  • Available colors and styles: 6
A Sleek, Block-Heel Bootie

These sleek ankle boots will look perfectly polished with a pair of skinny jeans, and they’ve got a block heel that’s easy to walk in all day. The boots are made from faux leather with a slim, sock-like fit. Opt for the white boots for mod ‘60s style, or choose from classic black or snakeskin styles. There are even suede or shiny options.

One rave review: “These boots are PERFECT— comfortable, stylish, and well-priced. They look much more expensive than they are! I’ve worn them probably 10x and they are wearing well so far.”

  • Available sizes: 5 — 11
  • Available colors and styles: 6
These High Heel Ankle Boots That Come In Tons Of Styles

With high block heels and pointed toes, these ankle boots look so glam — and they come in lots of styles, including leopard print, bright red, and black with rhinestone embellishments. The faux leather boots have a soft faux fur lining and side zipper closures to maximize ease.

One rave review: “Very well made!!! Love the soft fuzzy lining of the inside of the boot. The arch is not [too] high and love the thickness of the heel. Boots are very comfortable, was able to wear them all day.”

  • Available sizes: 5 — 11
  • Available colors and styles: 10
A Lace-Up Oxford Boot Made From 100% Leather

A pair of skinny jeans is the perfect pairing for these Oxford boots with stylish brogue perforations. The lace-up boots are made from soft 100% leather and feature supportive latex insoles to help you stay comfortable all day. This specific boot is available in black or brown, but you can also opt for other bootie styles and classic Oxfords in a variety of colors.

One rave review: “Love this shoe! Wore them all over Italy for weeks without even breaking them in and never even so much as a sore spot! Plus they’re cute and go with everything!”

  • Available sizes: 6.5 — 10.5
  • Available colors and styles: 27
This Classic Combat Boot

These classic combat boots are timeless, featuring a chunky platform sole and lace-up front. They’re made from faux leather and available in two colors: basic black and black glitter. The boots also have a side zipper for easy on and off, so you can slip them on without untying those laces.

One rave review: “Bought these and they are SO comfortable. They are very stylish and look very good. Very good quality and material. You can dress them up or wear them casually. They are Perfect!”

  • Available sizes: 6 — 10
  • Available colors and styles: 3
A Stacked Heel Bootie With Metal Details

Featuring a metal detail at the toe and heel, pointed toes, and deep-V cutouts, these ankle boots have a bit of an edge. But that doesn’t mean you have to sacrifice comfort for style — the faux suede boots have sturdy stacked heels and padded footbeds which make them easy to walk in. Choose from four colors, including black and red.

One rave review: “Great shoe! I was shocked at how comfortable they are! So cute! Just like the picture. Gotten tons of compliments. Highly recommend.”

  • Available sizes: 5.5 — 12
  • Available colors: 4
These Low-Heel Ankle Boots That Are So Comfy

With low heels and memory foam insoles, these Dr. Scholl’s ankle boots are designed with comfort and style in mind. The boots have perforated microsuede uppers, deep cutouts on each side, and back tabs that make them easy to pull on and off. There are five neutral colors to choose from, including olive, brown, and black. If you’re looking for a pair that can handle all-day wear, definitely consider these.

One rave review: “I love these shoes, they are so comfortable...and stylish! They are a perfect fit and [look] great with my skinny jeans.”

  • Available sizes: 6 — 11 (including wide sizes)
  • Available colors and styles: 5
These Chelsea Boots With Lug Soles

These Chelsea boots with lug soles and chunky heels are so trendy and versatile — reviewers write that they’re “obsessed” and wear them with absolutely everything. The pull-on platform boots are available in three styles — sand-color suede, matte black, and classic black leather — and each one will look great with jeans, skirts, and more.

One rave review: “These are my new favorites shoes, without a doubt. They’re comfy, sooo cute, and perfect for winter fashion wear. So obsessed with them.”

  • Available sizes: 5.5 — 11
  • Available colors and styles: 3
These Suede Wedge Booties

These suede wedge boots are a comfy alternative to high heels with cushioned insoles and padded lining. The boots also have side zippers that make them easy to slide on and off. Plus, there’s a range of versatile colors to choose from, including burgundy, black, and taupe.

One rave review: “Not too narrow, not too wide, perfect for pairing with your favorite cuffed skinny jeans. High quality material and pretty easy to wipe clean. 5 stars!”

  • Available sizes: 5 — 11
  • Available colors: 13