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.
Half rain boot, half Chelsea boot, all set and ready for whatever your day has in store.
If you’re intrigued by the Western trend but not quite ready for a full cowboy boot, try these fun, fringed kicks instead.
It ain’t easy being green, unless you’re wearing these booties. In which case it’s both easy and stylish.
The animal print trend is still going strong and we’re very into this light and dark variation.
Charles by Charles David ($60)
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)
Is it a sock and a mule? Is it a comfy, cool bootie? Only you need to know the real answer.
Charles & Keith ($69)
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).
The tie at the top will ensure you find your perfect fit.
New Look ($72)
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)
Pairs well with trench coats, corgis and The Crown.
Charles & Keith ($79)
An everyday version of the most popular color combo from this year’s Emmy Awards.
Chinese Laundry ($80)
Not one for loud prints and bold colors? Dip your toe into leopard print with this minimalist variation.
Coconuts by Matisse ($90)
Though they’re advertised as city shoes, we bet you could take this chunky sole for a hike in the country.
You can never go wrong with a timeless, black suede boot. Especially when said boot has such a walkable heel.
Steve Madden ($102)
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)
This icy gray shade is a gorgeous nod to the cooler months ahead.
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)
Black and White Spots
Cruella de Vil would very much approve.
These are intentionally slouchy, so you don’t have to spend all day pulling them up.
ASOS Design ($135)
These come in a variety of shades, but we predict this faded hue of green will age particularly well.
Silent D ($138)
Combat-style boots can naturally feel a bit heavy, but bright white helps lighten things up.
Dr. Martens ($140)
Tall Snake Print
Another classic that will last for years to come.
Steve Madden ($150)
Your favorite flat, just as a stiletto instead.
Louise et Cie ($150)
So you can channel your inner cowgirl. Yee-haw!
Dolce Vita ($152)
A literal sock boot. Or, at least one that looks like a sock (and is likely just as comfy).
We highly advise weatherproofing these before wearing them out on the town.
Chinese Laundry ($160)
Not sure which colors will look best with your new dress? Why not combine a trio of hues into one?
A shiny, new take on the Chelsea boot.
Take a walk on the wild side. Literally.
Dolce Vita ($162)
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.
A bow is a delicate little detail that makes all the difference.
Kelsi Dagger Brooklyn ($175)
Leather laces and exaggerated eyelets give this Victorian style a modern refresh.
Free People ($178)
One of PureWow’s editors swears by these as the most comfortable heeled boots she’s ever owned.
Slim Work Boots
The contrast between the caramel tan suede and black laces makes these look like a refined Timberland.
Jeffrey Campbell ($178)
Perfect for hippies and cowboys alike.
Jeffrey Campbell ($190)
A row of pearls on the heel takes some of the toughness out of these leather Chelsea boots.
Lousie et Cie ($198)
We like to think of this bootie as cowboy lite.
Alias Mae ($210)
Though they might not be appropriate for an actual hike, they are weatherproof, making them an excellent choice for rainy days in the city.
Brown Cow Print
How now, brown cow?
Jeffrey Campbell ($225)
Get that vintage ’60s feel, without the hassle of vintage shopping.
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.
Yes, it also comes in black and brown, but we’re pretty enamored with this unexpected teal faux croc.
Sam Edelman ($250)
Your most fashionable friends will be green with envy.
Snake Print Stilettos
These tall, pointy-toe boots work wonders to lengthen your legs and give you supermodel gams.
Vince Camuto ($250)
The heel may look high, but it’s actually less than three inches, so your feet won’t feel tired by 6 p.m.
Western meets disco meets the inside of my closet.
White Cowboy Boots
A very glam cowboy, indeed.
& Other Stories ($279)
Keep that square-toe trend going into the cooler months.
’Tis the color of the season, after all.
Stuart Weitzman ($300)
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.