How to Wear Ankle Boots This Fall

An ankle boot is the most useful shoe a woman can own between October and March, and the one most often worn badly. Not because the boots are wrong, but because the hem above them is. Where your jeans, skirt or trousers stop decides whether the boot looks deliberate or like it wandered in from another outfit.

This season makes the case for owning a good pair stronger than usual. Fashion editors' October shopping predictions single out ankle boots with rounded and elongated toes, and the big fall boot reports point to slouchy shapes, buckle details and lighter browns such as cognac and chestnut. Here is how to choose a pair and what to wear with it.

Choose the shape first: four ankle boots, four jobs

Most wardrobes need one or two ankle boots, not six. Pick by what you actually wear on a weekday.

The slouchy boot. A soft shaft that collapses into folds around the ankle. It is the most current shape this fall and the most forgiving: it reads relaxed with jeans and softens a sharp coat. The Pamela slouchy stacked-heel ankle boots have a round toe and a low stacked heel, which makes them a realistic all-day shoe rather than an occasion one.
The sleek pointed boot. Close to the ankle, narrow at the toe. It lengthens the leg and works under trousers better than anything else. The Sylvie pointed ankle boots have a glossy finish that holds up with tailoring and dark denim alike.
The utility boot. Buckles, a lug sole, a bit of weight. The one to reach for on wet days and with heavier knits. The Diletta double-buckle lug-sole boots add height through the sole instead of the heel, so they walk like a flat.
The suede boot. Softer, warmer-looking, and the easiest way into this season's browns. More on that below.

If you are buying one pair, buy the shape that matches your trousers. Wide and cropped trousers want a slim boot; skinny and straight jeans can take almost anything.

Ankle boots with jeans: the hem is the whole trick

Three hem options work. Everything else is a compromise.

Cropped above the boot. A straight or wide-leg jean that stops an inch or two above the top of the boot, with a sliver of ankle or sock showing. Clean, current, and the best way to show off a slouchy shaft.
Tucked in. Skinny or very slim jeans only, tucked smoothly inside the shaft. Works best with a sleek boot; with a slouchy one, the folds and the denim fight for the same space.
Full length over the boot. A straight or bootcut leg long enough to fall over the boot and touch the top of the foot. The boot becomes a base rather than a feature, which is ideal with a pointed toe that peeks out at the front.

The hem to avoid is the one that stops exactly at the top of the boot, or bunches on it. It cuts the leg at its widest point and makes the boot look like it is a size too big.

Ankle boots with dresses and skirts

This is where fall outfits get easy. A midi dress with ankle boots covers the whole leg between hem and boot with only a few inches of skin or tights showing, which looks balanced and stays warm.

The rule is contrast in weight. A floaty dress wants a boot with some substance, like a lug sole or a block heel, so the outfit does not look like a summer look with boots added. A heavier knit dress can take something sleeker. The Amanda belted knit midi dress is a good example: worn with a pointed boot and a long coat, it is a full fall outfit with almost no thought required. The wider edit is in midi dresses.

With mini skirts and short dresses, go opaque. Black tights and a black ankle boot make one continuous line and keep the proportions tidy. Bare legs with ankle boots works in September; by late October it looks like you lost an argument with the weather.

A quick check for any skirt length: if the gap between hem and boot is roughly the same as the length of the boot shaft, it will look intentional. If the gap is much smaller, choose a taller boot or a shorter skirt.

Ankle boots with trousers

Tailored trousers and ankle boots are the most underused pairing in a fall wardrobe. Two versions work well:

Full-length straight trousers over a heeled boot. The heel adds the height the trouser needs to fall cleanly, and the pointed toe finishes the line. This is a work outfit that walks better than pumps.
Cropped wide-leg trousers with a slim boot. The boot should sit fully under the hem, not compete with it. Keep the boot and trousers in the same color family to avoid a visible break at the ankle.

Browse women's pants for straight and wide-leg cuts that suit both.

Brown, black or something else

Black is still the most versatile ankle boot, and if you only own one pair it should probably be black. But the fall boot reports are clear that brown is having the stronger season, with lighter, warmer shades like cognac and chestnut alongside the darker chocolate tones that have dominated autumn so far.

Suede is the easiest way to wear it. The nap gives a single brown depth, so it looks richer than a flat smooth finish. The Carmilla suede ankle boots in light brown have a pointed toe and a narrow heel, a dressier take that works with cream knits and dark denim. For something more casual, the Freya suede ankle boots have a rounded toe and snap-button cuff tabs, so the shaft can be worn close or turned down.

Burgundy is the other color worth considering. It behaves like a neutral with navy, gray and denim, and it is one of the supporting shades in this season's boot reports. If you already own black and brown, it is the most useful third pair.

Three mistakes to avoid

Bulky socks spilling over the shaft. If socks show, make them thin and either matching the boot or matching the trousers.
Ignoring the toe shape. A very round toe under a sharp trouser looks clumsy; a needle-point toe with baggy jeans looks borrowed. Match the toe to the mood of the outfit.
Suede in the rain without protection. Spray suede with a protector before the first wear and keep smooth or lug-sole boots for wet days.

Where to start

If you are building from nothing, start with a sleek black boot for trousers and dresses, then add a brown suede or slouchy pair for jeans. Between them, those two cover almost every outfit from now until spring.

The full range of heeled, flat, slouchy and buckled styles is in women's boots, and the rest of the season is in the women's Fall Drop. Most pieces are already marked down, and buying two, three or four items takes an extra 15%, 20% or 25% off on top.

How to Wear Ankle Boots This Fall: A Women's Guide