20 Ways to Style Ankle Boots
In my eyes, there are a select few pieces that you can wear year-round, regardless of if it’s the middle of June or the chilliest winter day—and on that list is ankle boots.
There is always an occasion for some cute ankle boots.
Maybe you’re attending a summer country music festival and you opt for a pair of short white boots. Or maybe you’re traipsing around Manhattan just as the first frost settles on the sidewalks.
Whether you’re a city lover, country girl or anything in between—it’s hard to go wrong with this universally beloved footwear.
But where do you begin when you’re looking for ways to style ankle boots?
Sometimes depending on how high up your ankle they go it may create a case of strange proportions. Other times they may feel too dressy or too casual.
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20 Ways to Style Ankle Boots
Don’t fret—I’m here to show you some real world examples of how I’ve styled ankle boots over the last several years that will address all of your styling questions.
Any time you feel the “what should I wear these with?” question sneaking up in your head when you’re trying to get dressed, pull up this post.
Not only that, but I’m also sharing some of my favorite colors and fabrics for ankle boots and my go-to pieces to pair ankle boots with so you can copy and paste my outfit formulas.
Outfit ideas with ankle boots
All white chic
Pairing ankle boots with a white mini skirt and t-shirt makes for a fresh, monochromatic look perfect for any city stroll.
Black skinny jeans
Black skinny jeans and ankle boots become one of my go-to combos in the colder months for an effortlessly cool, everyday outfit.
Cropped coat moment
Ankle boots are the perfect finishing touch for this look featuring a cozy, cropped coat look that balances style and warmth.
Classic denim mini
Take your classic denim mini skirt into fall with a sweater and ankle boots. This is an outfit I’d wear to work and then out to dinner making for an easy day-to-night transition.
Simple graphic tee
Give your simple graphic tee some flair by pairing it with a mini skirt, blazer and ankle boots for an easy, laid-back look.
Light wash jeans
Light wash denim and ankle boots create the ultimate casual combo. For this fall look, I also added a floor-length cardigan and a newsboy cap.
Long cardigan comfort
Stay cozy and chic with an oversized cardigan, styled with ankle boots for a versatile, layered fall outfit. To elevate this outfit I paired it with a leather top and skirt.
Mesh top edginess
A mesh top layered over a bodysuit plus the ankle boots and denim shorts brings a little edge to your typical weekend wear.
Mid-length faux fur coat
A bold mid-length faux fur coat and matching red purse take center stage while ankle boots tie the outfit together, matching the top and sunglasses.
Plaid skirt charm
A plaid skirt is made more accessible and less preppy when paired with ankle boots. Pair it with other neutral shades like gray and black for a New York chic outfit.
A dose of red
Bright colors and ankle boots are a great way to inject personality into your everyday wardrobe. The red top is a bold choice but the leopard print ankle boots sprinkle in more neutral colors.
Puffer jacket perfection
The chunky puffer jacket meets sleek leather ankle boots for an ideal combo of warmth and style in the colder months.
Sweater with puffed sleeves
One of my ultimate fall outfit combinations is a statement sweater (in this case one with puffed sleeves) and skinny jeans balanced with a pair of chic ankle boots.
Ripped denim revival
Give your ripped jeans an effortlessly cool upgrade by pairing them with ankle boots and a leather jacket for a laid-back look.
Oversized winter scarf
In the coldest New York winter months, I’m rarely seen without a giant scarf. This bold accessory is the statement of this outfit without a doubt, balanced by some suede ankle boots.
Bold statement top
Add flair to your ankle boots outfit with a statement top in an interesting fabric that brings instant interest and confidence to your look.
Straight leg style
Ankle boots perfectly complement straight-leg jeans, adding a touch of modern elegance to a timeless staple and meet right where the hem of the jeans ends.
A Western twist
Combine a western-inspired look like this fringe vest and suede mini skirt with ankle boots for an outfit that’s both fun and fashion-forward.
Wide leg trousers
Wide-leg trousers paired with ankle boots make a bold statement and make your legs look super long. In this case these pink corduroy pants contrast with the chic black ankle boots.
Colorful wrap dress
To balance out this nearly rainbow wrap dress, a pair of black ankle boots instantly makes the look more street style friendly versus stumbling around in a pair of heels.
Best pieces to pair with ankle boots
Skinny jeans
I love wearing skinny jeans with my ankle boots because they go so perfectly together. I love how this denim style elongates my legs and tucks into the boot meaning that there’s no uncomfortable rubbing around my ankle.
Wide-leg pants
Whether it’s a pair of relaxed denim or some wide-leg trousers, these are so fun to style with ankle boots. Often this means that the boot will just be poking out from underneath so it’s a chance to add some interest with a boot in a bold color or pattern.
Mini skirt
When it comes to transitional weather, I love having a closed-toe shoe to pair with a skirt as the temperatures change. In the spring and fall you can see me wearing ankle boots paired with a mini skirt along with a long-sleeve top, winter cardigan or light jacket.
Midi dresses
Ankle boots are probably my favorite shoe to pair with a midi dress because the proportions hit just right. If the dress length is on the longer side, you may choose a pair with heels and if the hem hits on your calf, a flat bottom boot could be a nice complement.
Best ankle boots colors to wear
Black: it’s hard to go wrong with something that pairs with everything.
Tan/brown: a neutral color ensures that you’ll always have a bit of balance.
Patterned: throwing in a boot in a fun pattern like a paisley or leopard print is a great way to level up your outfits.
Best ankle boots fabrics
Leather: for any outfit that needs a sophisticated touch, this super sleek fabric will do just that.
Suede: if you want to soften an outfit slightly, suede is a fun texture to incorporate into your look.
Snakeskin: for something a bit edgier, a snakeskin boot will add interest and dimension to even the simplest outfit.
I hope you’re feeling excited and inspired now that you have lots of ideas for how to style ankle boots and you’re thinking about the colors and fabrics that you may want to incorporate into your wardrobe.
I can’t wait to hear about how you’re styling ankle boots this year! Leave me a comment and tell me your favorite way to style them.
yours,
Austen