Our Edit Of Comfortable Autumn Ankle Boots (That Don't Look Like Comfort Shoes)

Every autumn there is a brief moment when ankle boots seem like the answer to everything, right up until you remember why half the pairs in your wardrobe rarely make it past lunchtime. The beautiful pair pinches. The sensible pair is technically faultless but somehow never the one you actually want to wear, arguably thanks to that dubious orthopaedic-looking sole. And the supposedly comfortable pair has an unfortunate habit of announcing that fact before you've even left the house.

In our humble opinion, the most comfortable ankle boots that still look polished usually have three things in common: a lower heel, a softer or more flexible upper and a sole that isn't unnecessarily heavy. None of that sounds especially revolutionary, which is rather the point. The best boots this season aren't trying to reinvent footwear. They're simply becoming easier to live with, so you don't leave them at the back of the wardrobe for another year. Flats are sleeker all round, sock boots are back, Western styles have been pared down and heels are shrinking into something that won't have you calculating the distance from dinner to the taxi rank.

Keep reading for the five defining autumn ankle-boot shapes we'd look for now, and the details that make each one easier to wear without sacrificing the whole reason you wanted a fancy new pair in the first place.

Gone are the days when a lack of heel made you feel a bit frumpy. Flat ankle boots look most current now when the sole gets quieter and the silhouette gets sharper. They're a long way from the chunky, practical styles we've become used to seeing in recent years. The line sits closer to the ankle and the toe is often subtly squared, almond-shaped or gently pointed, depending on the look you're going for.

For comfort, the flat heel is only part of the story. Supple leather, suede or a little stretch through the shaft can make more difference after an hour's walking than the heel height alone. Cushioning underfoot helps too, particularly if the sole is slim rather than padded-looking. This is the ultimate all-rounder: it gives tailored trousers a cleaner finish, works neatly beneath longer jeans (barrel legs especially) and won't make a dress feel as though it has suddenly become a winter outfit.

For autumn 2026, a little heel will take you a long way. The sweet spot is roughly 30 to 50mm: enough to give you some lift, but not enough to make walking home feel wildly optimistic. Itty-bitty kitten heels, once a dirty word, are firmly back, alongside small block heels and sculpted shapes. Square toes are having a moment too, and work particularly well here: slightly '90s, distinctly modern and, in a softer shape, often roomier than a sharp point.

Wear them with jeans and a blazer, under wide-leg trousers for work or with a midi dress for dinner. They're the answer when a flat feels a little too sensible but a high heel feels like hard work.

Western boots are still very much around for autumn, but the versions worth wearing now have lost some of the rodeo. Rather than combining every Western detail at once, the better ones borrow just one or two: a softly pointed toe, a curved topline, a little subtle embroidery. We'll even allow a touch of fringing, if you must. That restraint makes them surprisingly useful. They look good with straight or slightly cropped jeans, where you see enough of the shape for it to register, but they can also give a simple dress or skirt more character without requiring you to carry a hat and pistol to brunch.

Suede softens the effect further, as do brown, taupe and quieter neutral shades. If comfort is the priority, avoid the tallest shafts and most exaggerated heels and stick to a moderate Cuban or block heel. The trick to wearing them well is to notice the shape before you notice the theme.

Now bear with us on this. Wedge boots are one of those ideas that can sound rather alarming until you see the new versions that change your mind. Forget the heavy, platformed shapes that dominated years ago. The current wedge is cleaner, slimmer and often worked so neatly into the sole that it reads as sculptural rather than retro. It gives height and stability without the bulk, so it looks especially good peeking out from a tailored trouser or a midi skirt.

And the comfort? A wedge spreads height across more of the foot than a narrow heel, which makes it feel steadier and easier to walk in. The best new-season examples keep the rise moderate and the upper close to the foot, so you get the lift without the sense that the shoe is wearing you.

The Chicer, Slimmer Chelsea Boot

A Chelsea boot never really disappears, but its proportions do change. After several seasons of oversized soles and substantial treads, the more useful direction now is cleaner, slimmer and, well, chicer. That means keeping the parts that made the Chelsea boot indispensable in the first place, the elasticated sides, the easy pull-on shape and enough substance for unpredictable weather, while losing some of the visual weight that makes them feel like countryside cosplay.

The new Chelsea should look as good under tailored trousers as it does with jeans: slim enough for smarter clothes, practical enough to wear all day. It sits neatly beneath tailoring without a bulky break at the hem, works with denim at the weekend and gives a dress enough weight without tipping the whole outfit into deep winter.