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How to Wear Ankle Boots: 5 Chic Winter Outfits

How to wear ankle boots in 5 easy steps: with knit sets, sweater dresses, maxi skirts, trousers and button shirts. Real looks with notes on every piece.

By How Do You Fashion · Updated · 3 min read

How to Wear Ankle Boots: 5 Chic Winter Outfits

Ankle boots are one of the most useful shoes you can own in winter. They work with skirts, dresses and pants, but the right length and color make a big difference. Here is how to wear ankle boots in 5 easy steps, with real outfits and notes on every piece.

Quick answer: Wear ankle boots with long knit skirts, sweater dresses, maxi skirts or straight trousers. Let long hems touch the top of the boot, and match the boot color to your outfit for a long, clean look.

Step 1: Match Your Boots to a Knit Set

Woman in a light grey knit skirt set and cream ankle boots by a bike rack1Cream ankle boots2Matching knit skirt set
Photo: Noore on Instagram

A long knit skirt set with ankle boots in the same soft color looks clean and very chic. The boots peek out under the hem and keep you warm.

Quick tip: Light boots with light outfits make you look taller.

Step 2: Add Chunky Boots to a Sweater Dress

Woman in a long cream sweater dress, brown scarf and chunky black ankle boots1Chunky black ankle boots2Big wool scarf
Photo: Olivia Faeh on Instagram

Chunky black ankle boots make a soft sweater dress look cool and city ready. A big scarf adds warmth and color.

Quick tip: Pick boots with a thick sole for wet winter days.

Step 3: Wear a Maxi Skirt and Long Blazer

Woman in an oversized black blazer, black slit maxi skirt and chunky ankle boots1Lug sole ankle boots2Oversized black blazer
Photo: A Style Edit on Instagram

All black with a long blazer, a slit maxi skirt and lug sole boots looks sleek and strong. The slit shows a little of the boots when you walk.

Quick tip: A slit skirt makes walking in boots easier.

Step 4: Try Printed Boots With Plain Pants

Woman sitting in a cozy chair in an olive knit top, burgundy pants and tiger stripe ankle boots1Tiger stripe ankle boots2Olive knit top
Photo: Lucy Williams on Instagram

Printed ankle boots are a fun way to add style to a simple outfit. Wear them with plain pants and a solid knit so the boots stand out.

Quick tip: Keep the rest of the outfit in two simple colors.

Step 5: Pair a Button Shirt With a Belted Skirt

Woman in a blue button shirt, studded belt, long black skirt and pointed ankle boots1Pointed black ankle boots2Blue button shirt
Photo: Francesca Saffari on Instagram

A blue shirt tucked into a long black skirt with pointed ankle boots is a smart look for work and dinners. A belt adds a cool detail.

Quick tip: Pointed boots look sleek with long skirts.

Mistakes to Avoid With Ankle Boots

  • Wearing midi skirts that stop just above the boot with a big gap of bare leg
  • Pairing heavy chunky boots with very thin, delicate fabrics
  • Picking a boot color that fights with your outfit
  • Tucking wide pants into ankle boots, let them fall over instead

FAQs

What do you wear with ankle boots in winter?

Long knit skirts, sweater dresses, maxi skirts, straight trousers and jeans all look great with ankle boots.

Can you wear ankle boots with a dress?

Yes. Sweater dresses and long dresses look best, especially with chunky or pointed ankle boots.

What color ankle boots are most useful?

Black is the most useful, and cream or brown look great with soft neutral outfits.

Are chunky ankle boots still in style?

Yes. Lug sole and chunky ankle boots are very popular and practical for winter weather.

Ankle Boots Go With Everything

Choose the right hem length, match your boot color and add one fun detail. With these 5 easy steps, ankle boots will be your go to shoe all winter.

More ideas: winter boots outfits, how to style knee high boots and how to wear a skirt in winter.