How to Wear Ankle Boots: 5 Autumn Outfits

How to wear ankle boots comes down to one thing, and it is not the boot. It is where the hem of what you are wearing lands against the top of it.

Get that right and almost anything works. A hem that covers the boot completely, or one that sits well clear of it, both look deliberate. A hem that stops an inch above the boot leaves a gap, and the eye goes straight to it.

Five outfits below, built from boots on the shelf in Penarth now, from £54.99.

• The rule that decides everything
• How to wear ankle boots: five autumn outfits
• Choosing a heel you will actually wear
• At a glance
• Trying them on in Penarth
• Frequently asked questions

The rule that decides everything

Ankle boots cut the leg at the narrowest point above the ankle. Everything else follows from that.

• Cover the boot entirely. Wide leg trousers, straight leg jeans and a long hem all work this way.
• Or clear it by a good margin. A midi hem that finishes mid-calf leaves enough leg on show that the break reads as intentional.
• Watch the inch of skin between a cropped hem and the boot top. Either lengthen the hem so it covers, or take it up so it clears.

Colour helps too. A boot close to the tone of your hem or your tights keeps the line of the leg going. A contrasting boot stops it, which is fine when you want the boot noticed.

How to wear ankle boots: five autumn outfits

1. Wide leg trousers and a low block heel. The PINNS 778T Super Soft Wide Leg Trouser at £45.99 is cut in a soft stretch fabric that drapes rather than holds a crease. Wear it over the Marco Tozzi 25377 Cognac Boot, £89.99, a smooth leather ankle boot with a rounded toe, a gold buckle at the ankle and a 45mm block heel. The heel gives the trouser just enough lift to clear the floor.

2. A check trouser and a plain chunky boot. The PINNS 420T/S, £45.99, is a pull-on ponte trouser in a cocoa check or plain black, with the same easy waistband as the 778T. A patterned trouser wants a plain boot under it, and the Lunar Bessy Black Patent Ankle Boot at £54.99 does that job: a Chelsea shape with an elastic side panel and a chunky cleated sole, heavy enough to anchor the check without competing with it. Over the top, the Jessica Graaf 32455 Plain Jumper at £75.99, with its wide round neck, three-quarter sleeves and button detail along the shoulder.

3. A midi shirt dress and a pointed toe. The K Design D205 Midi Shirt Dress, £99.99, has a collar, a button-through front, long sleeves and a floral print. A midi hem cuts across the calf, so a pointed toe is doing useful work here: the Tamaris 25383 Taupe Boot at £64.99 is a suede point on a 55mm heel, and the taupe carries the line of the leg on rather than chopping it.

4. Evening, with a higher heel. The Tamaris 25395 Merlot Boot, £79.99, is the dressiest of the five. A deep merlot ankle boot on an 85mm block heel, so it gives real height while staying steady on a pavement. Pair it with the Cream Drakie Midi Jacket at £109.99, a straight cut that finishes mid thigh, and the whole outfit reads as evening without a dress in sight.

5. Weekend, with a lace-up. The Heavenly Feet Milford Black Boot, £64.99, is a chunky lace-up with a side zip and a memory foam footbed. It goes with jeans and not much thought, which is the point of it. This is the boot for the school run, the dog and a walk along the pier.

The rest of the shelf is in ankle boots, and the pieces above sit in trousers and jeans, jumpers and casual dresses.

Choosing a heel you will actually wear

Heel height decides how often a boot leaves the wardrobe. These are the four heights on the shelf and what each one is for.

• Flat to low cleated, like the Lunar Bessy and the Heavenly Feet Milford. All day, any surface, no thinking required.
• 45mm block, like the Marco Tozzi 25377. The everyday smart heel. High enough to change the line of a trouser, low enough for a full day on your feet.
• 55mm slim, like the Tamaris 25383 taupe. For dresses and skirts, where the point and the heel work together to lengthen the leg.
• 85mm block, like the Tamaris 25395 merlot. Evening height, but on a block rather than a stiletto, so it holds steady.

A block heel spreads your weight across a wider base than a stiletto. That is why most customers who say they cannot wear heels get on fine with a 45mm block.

At a glance

• Five ankle boots on the shelf now, £54.99 to £89.99
• The rule: cover the boot completely, or clear it by a good margin, and never leave an inch of skin in between
• Heel heights from flat cleated up to an 85mm block
• Wide leg trousers and long hems cover the boot, midi hems want a pointed toe
• Matching the boot to your hem or tights keeps the leg looking longer
• Fitted in store at The Queen B Boutique in Penarth, near Cardiff

Trying them on in Penarth

Boot fit is about width and instep as much as length, and neither shows up in a size. Come in and walk a few steps in them, and bring the trousers you plan to wear if you want to check the hem against the boot top properly.

Everything above is in the shop as well as online, and the wider casual clothing rail is there to build the rest of the outfit around them.

Shop Ankle Boots

Frequently asked questions

How do you wear ankle boots with wide leg trousers?

Let the trouser cover the boot completely. The hem should finish close to the floor, with the heel giving it just enough lift to clear the ground when you walk. A low block heel of around 45mm does this well, because it raises the hem without tipping you forward. Keep the boot slim through the ankle so it does not bulk up underneath the fabric. If the trouser is a touch long, that is better than a touch short, and any alterations should be done with the boots on your feet.

Can you wear ankle boots with a midi dress?

Yes, and it is one of the easiest autumn outfits there is. The thing to watch is the gap between the hem and the boot. A midi that finishes mid-calf leaves a clear stretch of leg, which reads as deliberate. Choose a pointed toe rather than a round one, because the point continues the line of the leg where a midi hem cuts across it. Matching your tights to the boot, or the boot to the hem colour, keeps the whole line going.

What tights or socks do you wear with ankle boots?

With a dress or a skirt, opaque tights in a shade close to the boot give the longest line. With trousers or leggings, an ankle sock that sits below the boot top keeps everything out of sight. Avoid a thick sock turned over the boot unless the boot is a chunky lace-up style, where it belongs. In a suede boot, a thinner sock keeps the fit true, since suede has less give than leather once it warms up.

Do ankle boots make your legs look shorter?

Only if the boot contrasts sharply with what is above it. The break at the ankle is a visual full stop, so a black boot under a bare leg or a pale hem stops the line and shortens it. Keep the boot, the tights and the hem in the same tonal family and the leg reads as one length. A pointed toe helps as well, since it adds length at the front without adding height.

What heel height is best for everyday ankle boots?

Around 45mm on a block is the height most customers wear most often. It lifts a trouser hem, changes the line of the leg and still lasts a full day on your feet, because a block spreads your weight across a wider base than a stiletto does. Save the 85mm for an evening. If you are on your feet all day or walking on uneven ground, a flat cleated sole is the sensible choice and still looks smart with a trouser.