Need A Transitional Piece? Try These Ankle Boots You’ll Want To Wear All Autumn Long

I’m not sure if it’s just me, but right around August is when I start craving cool weather outfits. Cold temperatures definitely bring out some great pieces in my closet, from cozy sweaters to comfy leggings. But one thing that always gets a heavy rotation? Ankle boots.

While on vacation in Savannah a few years ago, I must have had a far away dream-like look on my face, because my husband Paul asked me what was on my mind. I shrugged and didn’t say much; he blew me away when he asked, “You’re thinking about ankle boots, aren’t you?” He was right. Paul knows me.

I have several pairs of ankle boots, and before you begin to say they’re all alike, let me stop you right there: you need pairs of different shaft height, width, and heel height. This isn’t up for debate, my friends…it’s practically science. I wear my ankle boots well into summer, but that’s an advanced style move I wouldn’t recommend unless you’re ready for it. Issa vibe.

Scroll down to see the season’s best ankle boots that you’ll want to wear every day through fall (and maybe into next summer).


Steve Madden Aquarius Tan Suede


If you’re looking for ankle boots that can go with pretty much any outfit, then the Steve Madden Tan Suede Ankle Boot has you covered. The block heel offers stability and comfort, the height of the shaft offers a bit of toughness while also stabilizing your ankle. And the pearl-like studs say ‘I’m a lady, dammit.’

SHOP NOW – $139.95



Marc Fisher Mayden

With a taller heel and a more minimalist profile, this boot would pair just as well with a maxi dress as it would with a pair of jeans. I’d wear them with a monochromatic outfit and a pair of tortoise-shell sunglasses. And definitely a red lip.

SHOP NOW – $99.99

Marc Fisher Ulora Bootie

My all-time favorite combo in the fall: a low-heel, low profile ankle boot that I wear instead of sneakers. Weatherproof the suede before you wear ’em each season, and they’ll last forever.

SHOP NOW – $59.98



Matisse Caty

The best thing about these faux snake ankle boots is that you can go from witchy boho vibes to sleek biker badass whenever you feel like it. Wear with a maxi skirt for boho goddess energy or wear with dark denim for a tougher look.

SHOP NOW – $205

Lulus x Matisse Spirit

Another pair that goes with everything, this pair has a 2.5″ block heel and a rubber sole (which is fantastic for those of us who are slip-prone). When I wear a pair like this with pants, I usually wear a pair of meant-to-be-seen socks so that they’ll provide a colorful little peek when I sit down.

SHOP NOW – $54



Maps Chelsea Boot

Love ’em or hate ’em, Chelsea boots are perfect for those whose feet swell during the day. The elastic at the ankle accommodates swelling, plus it helps the wearer take the boots on and off. Wear with rolled up jeans, an old t-shirt, and a moto jacket.

SHOP NOW – $69.95

Asos Stradivarius

An ankle boot with a heel is always a good thing. An ankle boot with a back zip is a cause for celebration. These boots have the trendy square toe box, and a sleek, minimal look. These shoes mean business, so they’d be perfect for the office.

SHOP NOW – $45.90



Lulus Chic Taupe Boot

These Lulus boots are a nice compromise for those who don’t like the elastic of a traditional Chelsea boot. The gusseted panels hide the elastic, while still providing the wearer with ankle stability while allowing the boot to come on and off the foot easily. Wear with leggings for an instant outfit upgrade.

SHOP NOW – $38

Free People New Frontier Western Boot

Before you pause at the idea of a Western boot, realize that the notched front creates a v-shape – which visually elongates your leg, as opposed to typical ankle boots which form a straight line at your ankle bone. While not so important when you’re wearing pants, the effect can pull together your look when wearing a dress or skirt.

SHOP NOW – $148



Vince Camuto Retinsa Combat Boot

Sure you don’t really NEED a combat boot, but you don’t need dessert either. Life would be pretty boring without dessert, just as life would be boring without combat boots. If you’re going to wear combat boots though, you have to embrace the clunky factor, so I pair mine with slouchy cropped pants and a slim-fit t-shirt.

SHOP NOW – $99.99

Vince Camuto Gallzy Chain-Detail Boot

Extra in all the right ways, these are the shoes you reach for when you want to look like a Vegas showgirl who married the billionaire gambler and is now dropping their son off at boarding school in Switzerland. I mean that as the highest compliment.

SHOP NOW – $139



Free People Going West Boot

Subtle, lush, and caramel-smooth, these boots are the antithesis of flashy. These are the shoes of quiet revenge, simmering cordiality. The boots that square their shoulders and hiss “they don’t even know who they’re dealing with” when the going gets tough. If life were a buddy movie, these boots would team up with the chain-detail boot from above and pull off the perfect heist.

SHOP NOW – $88


These boots were made for walking, but we’re running to the store to get them! What were your favorites? Comment below!

For More Fashion Tips, Check Out These Articles:

Roller Skates Are In Again, And We’re Loving 2021’S Super Fashionable Styles

Looking For A New Work Bag? These 15 Totes Are Fashionable And Functional

Join the Conversation