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Some call it “back to school” season, but around here, it’s more like “back to boot” season. As an homage to our favorite fall footwear, we’ve rounded up the 50 best pairs, from ankle to sock to Western and every style in between, so you can live your best, most fashion-forward autumn to date.

RELATED: 30 Transitional Outfit Ideas for Every Day This September

naturalizer waterproof white chelsea rain boot

Waterproof White

Half rain boot, half Chelsea boot, all set and ready for whatever your day has in store.

Naturalizer ($30)

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splendid fringe boots

Wrapped Fringe

If you’re intrigued by the Western trend but not quite ready for a full cowboy boot, try these fun, fringed kicks instead.

Splendid ($50)

asos green ankle boots

Green Leather

It ain’t easy being green, unless you’re wearing these booties. In which case it’s both easy and stylish.

ASOS ($56)  

charles by charles david snake print boots

Two-Tone Snakeskin

The animal print trend is still going strong and we’re very into this light and dark variation.

Charles by Charles David ($60)

sarto by franco sarto white ankle boots

Stark White

A timeless classic you’ll wear for seasons to come. (Psst, plain leather versions are the easiest to clean. Just be sure to spray them with a protectant before your first wear and don’t forget to wipe them off at the end of the day, before you stow them back in your closet.)

Sarto by Franco Sarto ($60)

charles and keith black boots with ankle strap
NordstromCharles & Keith

Faux Strap

Is it a sock and a mule? Is it a comfy, cool bootie? Only you need to know the real answer.

Charles & Keith ($69)

sbicca corduroy boots


These textured booties are the cutest way to pay homage to the ’70s trend and much better than our old corduroy pants (that, TBH, feel a bit too on the nose).

Sbicca ($69)

new look over the knee boots for wide calf

Wide-Calf Over-the-Knee

The tie at the top will ensure you find your perfect fit.

New Look ($72)

charles and keith lace up boots
Charles & Keith

Victorian Lace-Up

The red shoelaces remind us of Cheryl Strayed’s hiking boots in Wild and make them feel a bit less intimidating than an all-black pair.

Charles & Keith ($73)

charles and keith plaid tall boots
Charles & Keith

British Plaid

Pairs well with trench coats, corgis and The Crown.

Charles & Keith ($79)

chinese laundry two tone boots
Chinese Laundry

Color-Blocked Pink

An everyday version of the most popular color combo from this year’s Emmy Awards.

Chinese Laundry ($80)

coconuts by matisse black leopard print boots

Subtle Leopard

Not one for loud prints and bold colors? Dip your toe into leopard print with this minimalist variation.

Coconuts by Matisse ($90)

mango hiking boots

Contrasting Laces

Though they’re advertised as city shoes, we bet you could take this chunky sole for a hike in the country.

Mango ($100)

RELATED: Cozy Girl Fall Is the New Hot Girl Summer and Here Are 12 Pieces to Prove It

steve madden black over the knee boots
Steve Madden

Classic Over-the-Knee

You can never go wrong with a timeless, black suede boot. Especially when said boot has such a walkable heel.

Steve Madden ($102)

nine west beige croc boots

Beige Croc

Dress them up with a velvet cocktail dress for Thanksgiving, or down with cropped jeans and a sweater for dinner with friends.

Nine West ($119)

aerosoles gray ankle boots

Sock-Like Shaft

This icy gray shade is a gorgeous nod to the cooler months ahead.

Aerosoles ($120)

dr scholls low black ankle boots
Dr. Scholl’s Shoes

Subtly Western

This year’s version of the black ankle boot features a curved rim and chunky heel. See ya later, last year’s form-fitting knit bootie.

Dr. Scholl’s ($125)

RELATED: Podiatrists Say *This* Is the Best Time of Day to Shop for a New Pair of Heels

aldo black and white animal print boots

Black and White Spots

Cruella de Vil would very much approve.

ALDO ($130)

asos slouchy brown over the knee boots

Slouchy Over-the-Knee

These are intentionally slouchy, so you don’t have to spend all day pulling them up.

ASOS Design ($135)

silent d green leather boots

Khaki Leather

These come in a variety of shades, but we predict this faded hue of green will age particularly well.

Silent D ($138)

dr martens white combat boots

White Combat

Combat-style boots can naturally feel a bit heavy, but bright white helps lighten things up.

Dr. Martens ($140)

steven madden tall snake skin boots
Steve Madden

Tall Snake Print

Another classic that will last for years to come.

Steve Madden ($150)

louise et cie heeled loafer boots

Heeled Loafer

Your favorite flat, just as a stiletto instead.

Louise et Cie ($150)

dolce vita cow print boots
Dolce Vita

Cow Print

So you can channel your inner cowgirl. Yee-haw!

Dolce Vita ($152)

everlane ribbed sock boots

Ribbed Knit

A literal sock boot. Or, at least one that looks like a sock (and is likely just as comfy).

Everlane ($155)

chinese laundry beige stiletto boots
Chinese Laundry

Off-White Suede

We highly advise weatherproofing these before wearing them out on the town.

Chinese Laundry ($160)

seychelles tri color boots

Tri-Color Leather

Not sure which colors will look best with your new dress? Why not combine a trio of hues into one?

Seychelles ($159)

vagabond metallic heeled chelsea boots

Metallic Stilettos

A shiny, new take on the Chelsea boot.

Vagabond ($160)

dolce vita cheetah print hiking boots
Dolce Vita

Cheetah Hikers

Take a walk on the wild side. Literally.

Dolce Vita ($162)

RELATED: 7 Outfits That Prove a Sweater Dress with Boots Is Perfect for Fall

aerosoles navy blue ankle boots

Buckled Booties

Yes, that heel is almost four inches. But this boot also features a new technology unique to Aerosoles that redistributes your weight so it’s more evenly spread between heel and toe.

Aerosoles ($170)

kelsi dagger brooklyn boots with bow

Bow-Back Boots

A bow is a delicate little detail that makes all the difference.

Kelsi Dagger Brooklyn ($175)

free people lace up boots
Free People

Two-Tone Lace-Ups

Leather laces and exaggerated eyelets give this Victorian style a modern refresh.

Free People ($178)

madewell ankle boots

Walkable Heels

One of PureWow’s editors swears by these as the most comfortable heeled boots she’s ever owned.

Madewell ($178)

jeffrey campbell lace up boots
Free People

Slim Work Boots

The contrast between the caramel tan suede and black laces makes these look like a refined Timberland.

Jeffrey Campbell ($178)

jeffrey campbell tie dye cowboy boots
Jeffery Campbell

Western Tie-Dye

Perfect for hippies and cowboys alike.

Jeffrey Campbell ($190)

louise et cie chelsea boots with pearl detail

Pearl-Adorned Heel

A row of pearls on the heel takes some of the toughness out of these leather Chelsea boots.

Lousie et Cie ($198)

alias mae brown boots
Stuart WeitzmanAlias Mae

Curved Rim

We like to think of this bootie as cowboy lite.

Alias Mae ($210)

sorel heeled hiking boots

Heeled Hiker

Though they might not be appropriate for an actual hike, they are weatherproof, making them an excellent choice for rainy days in the city.

Sorel ($220)

jeffrey campbell brown cow print boots

Brown Cow Print

How now, brown cow?

Jeffrey Campbell ($225)

jcrew houndstooth boots

Houndstooth Booties

Get that vintage ’60s feel, without the hassle of vintage shopping.

J.Crew ($228)

naturalizer tall black riding boots

Timeless Riding Boots

They may have a 3.25-inch heel, but we swear these will be some of the most comfortable boots you’ve ever walked in.

Naturalizer ($230)

sam edelman teal croc boots

Teal Croc

Yes, it also comes in black and brown, but we’re pretty enamored with this unexpected teal faux croc.

Sam Edelman ($250)

lms green croc boots

Green Croc

Your most fashionable friends will be green with envy.

LMS ($250)

vince camuto tall snake print boots

Snake Print Stilettos

These tall, pointy-toe boots work wonders to lengthen your legs and give you supermodel gams.

Vince Camuto ($250)

sezane leather ankle boots

Cognac Leather

The heel may look high, but it’s actually less than three inches, so your feet won’t feel tired by 6 p.m.

Sézane ($260)

ash black cowboy boots

Metallic Cap-Toe

Western meets disco meets the inside of my closet.

Ash ($275)

and other stories white croc cowboy boots
& Other Stories

White Cowboy Boots

A very glam cowboy, indeed.

& Other Stories ($279)

reformation square toe boots

Square-Toe Croc

Keep that square-toe trend going into the cooler months.

Reformation ($298)

stuart weitzman yellow orange sock boots

turmeric Suede

’Tis the color of the season, after all.

Stuart Weitzman ($300)  

mgemi two in one boots

Adjustable Shaft

Four hundred dollars is not a small amount, but if you think about it, you’re kind of getting two pairs at once. There's a snap under the fold of the shorter boot base, so you can switch up your look at a moment's notice.

M.Gemi ($448)

RELATED: 8 Transitional Jackets Our Editors Are Buying for Fall

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