Ankle boots have received a bad wrap in recent years. However, this confirmed millennial trend is set for a comeback—you just need to know which styles to choose, and what to wear with them.
When it comes to a modern interpretation of the ankle boot, trending styles range from slouchy and combat, to tapered and pointed.
For a casual wear, the bohemian aesthetic is seeing slouchy, suede styles re-appear in wardrobes, worn with flowing dresses or ruffled lace mini skirts. Meanwhile, moto and ‘indie sleaze‘ styles are thrusting combat boots, Doc Martens and other contemporary utility styles back onto feet.
On the more formal end of the spectrum you’ll find classic ankle boots with block heels, or kitten heeled ankle boots with a tailored fit and pointed toe, which all look good with trousers or maxi dresses.
Regardless of your chosen ankle boot style, there is one wardrobe item with whom they’ll always belong: the bootcut jean.
One could argue that boot and denim trends go hand-in-hand. And while we brace for the slow return of the skinny jean, other trending styles, like bootcut, sailor and straight-leg styles, are all a perfect companions for ankle boots.
But are we ready to embrace them with mini skirts or other wardrobe items? If you glance around the streets of fashion week, you might find the answer is, yes. Scroll on for ankle boot styling ideas.
What To Wear With Ankle Boots
Jump to your preferred style:
- Studded ankle boots
- Boho ankle boots
- Combat ankle boots
- Pointed toe ankle boots
- Animal print ankle boots
- Black ankle boots
- Brown ankle boots
Studded Ankle Boots
From creative heels to prints, there are various embellishments adorning today’s ankle boots. Studs are among the most versatile, aligning with other footwear trends of the moment. Style with a rocker’s edge and attitude, à la Kate Moss and her Isabel Marant booties.
Lolya Boot
ISABEL MARANT
Studded Leather Ankle Boot
KHAITE
Vintage Lover Bias Cut Mini Skirt
VRG GRL
Arizona Leather Jacket
ENA PELLY
Slouchy Boho Ankle Boots
The slouchy boot return is being pioneered by everyone’s favourite boot designer, Isabel Marant. Gathered at the ankle, these are a difficult look to style. You can opt for a more ’80s look, and tuck in your trousers. Or, wear them with a flowing, maxi dress to evoke that Flower Child essence.
Axiel Slouch Ankle Boot
WITTNER
Edrika Suede Ankle Boots
ISABEL MARANT
Halcyon Large Bucket Bag
ZIMMERMANN
Lisander Long Sleeve Dress
SIR.
Combat Ankle Boots
Biker and combat boots are popular among the style set, where they’re often worn to dress down a high-femme look. Popular amongst stylists who adhere to the ‘wrong shoe theory‘, pairing combat boots with an otherwise tailored or whimsical look is a great way to add interest—and show off your sartorial skills.
Cleated Mid Chelsea Boots
GANNI
Unisex 1460 White Stitch 8-Eye Boots
DR MARTENS
Double Loop Maxi Skirt
ST AGNI
Black Bonded Crepe Mix Jacket
GANNI
Pointed Toe Ankle Boots
For ankle boots that can be worn to a formal affair, your answer can be found in a delicate pointed toe. Sharp and dainty, these ankle boots can often be found with a kitten or stiletto heel. Wear beneath trousers and have the toe peaking out, or show them off with a skirt. Or, use the to dress up a basic denim and t-shirt combo.
Naomi 50 Bootie
STUART WEITZMAN
Seattle Boots
SANDLER
JW Anderson Straight Jeans
UNIQLO
Dia Car Coat
CAMILLA AND MARC
Animal Print Ankle Boots
Whether you have leopard, cow print, snakeskin, zebra or some other type of animal print ankle boots, you may need to put a little more planning into your styling. For some people, a gregarious and daring sense of style comes naturally. These people are probably already experts in pattern clashing or picking a colour palette. (Oh, to be this cool!) However, if you feel like you’re starting from square one when styling animal print shoes, a good rule of thumb is to stick to neutrals—blacks, browns, whites and creams. If your animal print is warm-toned, like leopard print, you could try a brown leather jacket and black trousers. A cooler-toned shoe print may look better with just black or white.
Bettina Leopard Print Ankle Boots
PARIS TEXAS
Coro Boots
M.N.G
The Clean Cut T-shirt
COS
The Reboot Bootcut Jeans
FRAME
Black Ankle Boots
You may already have a classic black ankle boot in your wardrobe. And if you don’t, consider this your sign! An must-have for a capsule wardrobe, a black ankle boot will be your best friend to wear with jeans all winter. Simple, unembellished cuban heel boots (as worn by Karlie Kloss, above) are a great gateway to build out your winter shoe-drobe. The mod-style block heel is another style that is both interesting but classic.
Louis Boots
NELSON MADE
Ryland Leather Ankle Boots
STUART WEITZMAN
Column Straigth Leg Jeans
COS
Souffle Yarn Crew Neck Sweater
UNIQLO
Brown Ankle Boots
If you’re leaning into warmer, brown tones this season, you’ll need a pair of boots to provide the reliable foundation for a look. Styles may vary, but there are certainly plenty to choose from. Mix with warm neutrals, like beige, cream and tan, and throw in a bag of a similar hue.
Dora Boots
NELSON MADE
Pointed Toe Ankle Boots
AEYDE
Spencer Stripe Silk Shirt
ASSEMBLY LABEL
Studio Bowling Bag Suede
COS
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