20 best ankle boots & booties your wardrobe needs in 2021

Black suede ankle boots fashion blogger Eve Dawes walking

Women’s Ankle Boots.
Stylish & fashion forward women’s ankle boots and booties you need to know about Fall/Winter 2021 – 2022

Ankle boots and women’s boots in general are one of my favorite fashions I look forward to every Fall and Winter. There’s so many women’s ankle boots and best booties to choose from in the Fall boots 2021 collections: Booties, heeled ankle boots, knee high boots, over the knee boots and I love them all!

There are so many different styles, colors, shaft and heel heights, it makes finding a style for every occasion and outfit possible. But it can get overwhelming so on this women’s boots 2021 list, I’m sticking to just ankle boots and bootie styles.

Best booties and ankle boots of all varieties for 2021/22

I’ve rounded up the top trends for ankle boots and booties this year. Including best for budget and designer options. As well as ankle boots and booties that are vegan, using faux leather or faux suede so there’s a boot for everyone.

Shop the Fall | Winter Boot Edit 2021

Women’s Ankle Boots | A curated list of trending boots and best booties for all budgets and tastes

Ankle boots of all colors, from pretty pastels to darker black and brown styles, leather, faux leather & suede, feminine to chunky grungy, trendy boots to classic styles, high heeled ankle boots to low heels comfy flats. The best ankle boot picks for 2021 – 2022 are all here including lots on sale. These are the styles seen on the Fall Winter 2021/22 runways and most likely to lead the way trend wise this Fall and Winter.

In between seasons and transitional styles can be tricky. That’s why I love ankle boots to get us through as they’re so much more versatile, versus under or over the knee boots, as they can be worn from late Summer into fall all through Winter into spring, with dresses or jeans, denim or leather jackets. With lots of different styles for whatever your fashion style or mood is.

If you’re still wondering How to Conquer In Between Season Fashion have a look at these outfits and fashion finds.

If you need a winter wardrobe update Winter Trending Neutrals, Statement Shoulders and Must Have Tops will give you some fashion inspiration.

Best ankle boots 2021 – 2022

The List of 20+ Styles

1. Trending Boots: Chunky flat lace up buckle black biker boots and Combat boots

I kept seeing these black leather chunky ankle boots all over Instagram with everything from summer dresses with an oversized cardigan to sweater dresses or leggings in 2020. In 2021 the combat boot trend’s continuing on. These chunky boots give a harder more grungy look and are a super comfortable option. The trend wasn’t forecast to last for 2021 but here we are!

These are the best chunky flat ankle boots I found from shopping around online and my favorite instagram influencers. Starting at under $20, with mid-range boots around $250 for the Kurt Geiger Sting and Stinger Biker boots and Balmain as the best designer chunky boots option.

I couldn’t resist adding the Kurt Geiger black leather boots as the leather looks so luxe and for the stud and buckle details. They come in 2 lengths, ankle and slightly longer but still not knee high by any means.

Kurt Geiger Stinger Boots Black Studded Leather (ankle boot version)

Kurt Geiger Stinger Studded black leather boots luxury fashion 2021

Kurt Geiger Sting Boots Black Studded Leather (taller version)

Kurt Geiger Sting boots black studded buckle flat style Selfridges Luxury Collection London

Best Designer Combat Boots for 2021/22 | Balmain

Balmain black flat combat boots ankle height

Chelsea boots

The Chelsea boot will always be quintessentially English to me. I remember growing up in the country side in England and wearing them with stirrup leggings to horse riding lessons.

Chelsea boots have come a long way since then and comes in different styles from classic to chunky soled to heeled. The beauty of these besides how comfortable they are is that they just pull on.

If you’re planning on walking and not just sitting pretty, these are one of your best options and are going to be one of key boot trends for Fall boots 2021.

Chelsea boots chunky sole Nasty Gal black leather ankle booties
Chelsea Boots | Photo courtesy Nastygal

The Chelsea boot goes way back to the Victorian era and the design’s the invention of the C J. Sparkes-Hall, boot maker to Queen Victoria

I remember wearing them horse riding back in the 90’s! They’ve been around for a century and their classic style is here to stay.

Best Chelsea boot for budget

Black Chelsea boots Nasty Gal womens fashion
Black chelsea ankle boots | Photo nastygal

What makes a Chelsea boot

It’s the elastic sides. What gave them their name was back…

In the mid-1950s, a group consisting of young artists, film directors, and socialists started frequenting the King’s Road area in West London. This group was named the ‘Chelsea Set’ …they made the name ‘Chelsea’ synonymous with a new way of living and dressing…favoring the Paddock boots … the ultimate leisure accessory and hence were renamed to Chelsea Boots.

Gentleman’s Gazette Chelsea Boot Guide

On Trend Designer Chelsea boot

Designer Chelsea boot flat sole black faux leather Christian Louboutin
Christian Louboutin Chelsea Boots | Photo courtesy Net-A-Porter

Mid-High Heel Chelsea Boot

If you prefer a heeled ankle boot, the chunky heeled Chelsea boot is a great option. The chunky heel versions are still a comfortable option but gives us petite (or tall) girls a boost.

Best for budget

Classic Chelsea boots womens black  booties
Black mid heel chelsea boot | Photo courtesy Lulus

Top find for luxury

Prada black mid heel ankle boot pull on womens
Mid heel pull on ankle boot | Photo courtesy Neiman Marcus

Ladies boots – feminine styles & heeled ankle boots

These are my favorite booties. I’m 5’2” and high heels, feminine styles and pretty colors are my go tos.

All of these boots are under $30 and will be in the liketoknow.it Fall sale 2021.

Fall boots 2021 -2022 | Best booties and ankle boots for dresses

3 women fashion bloggers wearing fall boots 2021

I’m not sure if there is just one style of ankle boots or booties that’s ‘best’ for dresses! Pretty much any boots go with dresses depending on the look you’re going from. It’s such a versatile look you can put your own spin on from flirty and feminine to grungy biker chick.

Pick a style that expresses how you’re feeling and makes you feel good, there’s really no right or wrong.

Cowboy ankle boots + Boots with Chunky Heels

Cowboy boots were all over the Fall/Winter 2021 shows such as Isabel Marant. The key to making cowboy boots work for you is finding a color, shape and material you love. I’m never going to be the girl in the crocodile cowboy boots but cute white leather ankle cowboy boots I can get behind. Cowboy boots look super cute with denim shorts on warmer days and with a knit dress and Lack of Color hat on cooler days. 

I’ve always wanted cowboy boots ever since coming to America but it took me until last year to find the perfect pair.

fashion must have white cowboy ankle boots fedora Glamour Gains
Block Heel Pointed Toe Western Boots

The ones I have are ankle boots and white so they go with pretty much everything. Look for softer leather or double check the seams won’t rub and give you blisters if your socks aren’t high enough or you’re going sock-free.

Black suede cowboy ankle boots Block heel buckle detailing

Best Heeled Cowboy Boot | Luxury Buy

 These cognac brown cowboy boots are more of a calf height boot than an ankle boot but too good not to include. 

Designer Cognac brown leather cowboy ankle boots
Cognac high heel cowboy boots | Photo courtesy FORWARD

Best for budget

These brown faux suede women’s cowboy boots are super cute and the perfect color for Fall. They’re true ankle height with a mid-height block heel to give just a little height but still be comfort shoes.


Cute ankle boots for walking – most comfortable women’s flat boots | Fall Boots 2021

When my husband said I needed waterproof, warm, sensible snow boots for our winter travel I was thinking clunky, dorky and outdoorsy styles. I know it’s the smart thing but I wasn’t too crazy about it.

These white waterproof, insulated ankle boots are from The North Face last year and they check all of the practical boxes while still being a little stylish and giving me good grip so I don’t face plant.

I wore these waterproof boots in the rain and snow and they kept my feet warm and dry. If you want extra warmth you can always pop on a pair of wool socks.

Waterproof Ankle Boot Features

  • Upper: Waterproof-nubuck upper

  • Durable, water-resistant, 100% recycled P.E.T. ripstop baffling details

    See Also

  • Waterproof construction

  • 200 g PrimaLoft® insulation

  • High Rebound OrthoLite® footbed provides ultimate comfort

  • Sole Unit: Proprietary XtraFoam™ midsole for superior comfort; firmer-density EVA compound around the perimeter for stability

  • Durable TNF Winter Grip® rubber outsole

  • IcePick® temperature-sensitive rubber lugs for increased traction

Fashion blogger sat wine white snow boots The NorthfaceFashion blogger sat wine white snow boots The Northface

Fashion blogger wearing white Northface lace up snow bootsFashion blogger wearing white Northface lace up snow boots

If I’ve missed any ankle boots you’re loving this season, share them in the comments below.

LiketoKnow.it Fall Sale in App exclusive discount code – Get ready for 2021!

Many of these ladies boots were in the liketoknow.it app only sale Fall Sale. An in app exclusive sale which ran for a couple of days in September. The good news it happens every year so make sure to download the liketoknow.it app, follow me evedawes to get the exclusive discount code and save money!

To get in on the exclusive discount code you need to:

  • Download the LiketoKnow.it app

  • Follow me evedawes

  • Mark your favorite photos and/or items

  • Then from September 20th-22nd, these posts and items will be flagged with a big red LTK Sale label on them and give you the exclusive in app only sale code. So you can shop the sale before they sell out directly from the LiketoKnow.it app.

How shop liketoknow.it Fall Sale 2020 favorite now

How shop liketoknow.it Fall Sale 2020 favorite now

Scroll To Top