Fall-Winter 2026-2027 boots: which ones are truly worth choosing

Seasonal guide · Fall-Winter 2026-2027

A boot is the kind of shoe you buy in September and wear in November, which is why it's easy to get wrong: you choose it in twenty-degree weather, thinking about how it will look, not where you'll walk. The first question we ask in the boutique isn't what style you like, but how much time you'll spend outdoors and in what weather. From there, the choice narrows on its own.

This is a guide by style, highlighting what really works in each category. The full selection is in women's boots and men's boots.

The boots that arrived at the boutique in October

The category with the most new arrivals is shearling: UGG Classic Mini and Ultra Mini, also in the Western version, and Mou Eskimo boots. For snow, there are Moon Boot Icon Glance boots, both high and low, with a platform sole. Among the combat boots, new arrivals include suede Archyve boots with a central zip and tall boots with buckles; for a platform sole, choose Dr. Martens platform boots.

For him: waterproof Timberland boots and the leather Britton Drive, velour Fabi Chelsea boots, and calf suede Doucal's desert boots.

1. L'amphibian boot, if you want it to last ten years

Among women's combat boots, the eight-eyelet Dr. Martens 1460 is the benchmark: Goodyear welt, welded AirWair sole, leather that molds to the foot after breaking in and never goes back. It's the boot you only have to buy once, provided you get through the first two weeks — which are tough and should be tackled with thick socks and short distances.

The Pascal in Virginia leather version is the softest from the start and the right choice for anyone who doesn't want the classic break-in period. L's combat boot works with denim, a skirt with a visible sock and — surprisingly — tailored trousers, as long as they're the right length.

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Combat boots and Dr. Martens

Dr. MartensCombat boots 1460 SmoothDr. MartensBoots Dr. Martens 1460 in pebbled leatherDr. MartensBoots Dr. Martens 1B99 women's high boots in Virginia leatherDr. Martens1460 Ambassador Leather bootDr. MartensBoots JADON 3 platform boots in Pisa leatherDr. MartensBoots 1460 Pascal VirginiaDr. MartensBoots Sinclair leather platform bootsDr. MartensAnkle boots 2976 leather Chelsea boots with platform

2. The waterproof boot, for when it really rains

This is the category where we offer the widest selection, and that’s no coincidence: the waterproof leather Timberland Premium 6-Inch is our best-selling style of the cold season, because it solves a problem rather than follows a trend. People who walk, take the train, or take their children to school in the rain buy it again and again.

Also available in the Stone Street version with a platform sole, in camel suede, which adds a few centimeters of height and shifts the style from utilitarian to urban. One caveat: waterproof suede still needs to be protected with spray; the leather’s waterproofing does not protect the surface from stains.

3. Sheepskin, if the cold is dry

The UGG Classic Ultra Mini are short sheepskin boots: a shorter shaft, easy to slip on, with genuine shearling inside. They're very warm and are the choice for anyone taking short trips who wants to slip them on without thinking. This year, we also have them in pony hair with an animal print, a way to wear a classic without looking like everyone else.

It's worth noting the limitation: sheepskin is not waterproof. It's perfect in dry snow, but gets damaged on wet pavement. If your winters are more rainy than freezing, this isn't the right category — or save it for sunny days.

Alongside UGG, another name in sheepskin is Mou, recognizable by the thick handmade stitching along the edge. We've covered how they fit and how to clean them in our complete guide to Mou shoes.

4. The ankle boot you'll actually wear

It's the style with the most options in our selection, for a practical reason: it fits under trousers without fuss, works from morning to evening, and doesn't dictate an outfit. A mid heel — five or six centimeters — is the height that lasts all day.

On an ankle boot, the critical point is the shaft: it needs to close around the ankle without squeezing or leaving a gap for air to get in. If you have fuller calves, look for styles with side elastic or a long zip — it's the difference between a boot you wear and one that stays in the box.

Available now

The ankle boots we have now

Dr. MartensCombat boots 1460 SmoothTIMBERLANDBoots Stone Street Mid Warm LinedCoccinelleCoccinelle Ankle boots C-Saddle suede with buckleCoccinelleCoccinelle Ankle boots suede cowboy boots with 7 cm heelMoon BootMoon Boot padded suede and fabric ankle bootsTIMBERLANDWomen's Stone Street Mid Timberland boot with platform soleASHFAME women's ankle boots in suede with a 5 cm heelASHDark suede ASH Flare ankle boots with a mid heel

5. The Chelsea boot, the most underrated

Elastic side panels, no laces, a sleek profile: the Chelsea boot slips on in three seconds and is also the most formal style on the list. It works with a suit, where a combat boot would look out of place, and with jeans, where an ankle boot would look too feminine.

It’s also the only style that won’t forgive the wrong size: with no laces or buckles, the fit depends entirely on the elastic. If it slips around from the first step, it’ll always slip.

6. The après-ski boot that’s no longer just for the mountains

Moon Boot have moved beyond the ski resort and have been seen in the city for several seasons now. They’re the answer to the one situation where everything else fails — deep snow, real cold — and nobody expects them to be elegant. There are only a few styles, and this category sells out quickly when the first cold spell arrives.

Ankle boots in brown: from dark brown to leather

Black remains the safest choice, but this autumn brown ankle boots are no longer just an alternative: the brown biker boot is one of the season’s most talked-about trends. The reason is practical before it’s about fashion. Brown goes with everything black cuts off: light denim, camel, mélange grey, cream white. And with sheer tights, the contrast is less stark, so it lengthens the leg instead of breaking up the line.

Not all browns are worn the same way, though. Dark brown, almost black, is the easiest: it works where black would, but pairs more softly with blue and beige. Chocolate brown is warm and looks great with denim. Leather brown and camel are the most casual, perfect with jeans and harder to wear with a smart suit.

In the boutique, brown comes in almost every style. The biker is the Pinko in dark brown leather with a harness detail; the western style is the ASH Flare in dark brown suede, with shaped details inspired by the American West and a mid heel. For everyday wear, there's Copenhagen Studios: the CPH901 in chocolate calf suede, with a discreet buckle, and the brown suede combat boot with a lug sole. For those who want a tall boot, there's the ASH Dolly02 in dark brown suede, with a 41-centimeter shaft and a 5-centimeter block heel. You've already seen camel above: it's the Timberland Stone Street with a platform sole.

A note on care. Brown suede is more forgiving than light suede, but it still needs to be sprayed before its first outing. On smooth leather, use a cream in a matching shade or a colorless one, never the one you keep for black shoes: it darkens brown, and there's no going back.

Luxury Boots: What Justifies the Price

The difference between two boots that look identical in photos lies almost entirely where the camera can't reach: inside, underneath, and in the stitching. When customers in the boutique ask why one boot costs so much more than another, we turn it over and point out four things.

The leather. Good calfskin or calf suede has a tight, even grain; it develops a patina over time and does not crack at the creases. Leather covered with a thick finishing layer looks the same on day one and shows cracks after one winter. The Double Face by Casadei and the Copenhagen CPH901 are made of calf suede, while the New Double Face by Casadei is made entirely in Italy.

The lining. It’s the first place where costs are cut because it can’t be seen. A leather lining lets the foot breathe and doesn’t get clammy like synthetic material, and the same goes for the insole, which is in contact with the foot all day. L'ASH Dolly02, Chie Mihara ankle boots, and the CPH901 are lined in leather.

The sole, and how it’s attached. A sole stitched to the upper, like the Goodyear welt on Dr. Martens boots, can be replaced by a cobbler when worn: the boot gets a second life. A sole that’s only glued on usually can’t. Leather is the most elegant sole, but it slips on wet surfaces. That’s why Chie Mihara adds a non-slip rubber insert: the right compromise for city walking.

The details you appreciate over time. The leather-covered heel, which won’t chip at the first step like painted plastic. The zip that runs to the bottom of the shaft. An elasticated section hidden at the top, keeping the tall boot snug without pinching. These are things you appreciate on the tenth wear, not the first.

Here’s our rule: luxury boots should cost more upfront and less over time. If the sole can be replaced, the lining lets the foot breathe, and the leather improves with wear, the cost pays for itself over a few winters. If the logo is the only thing that justifies the price, it doesn’t. Our tall styles are gathered in the women’s tall boots collection.

Sizing, with no single rule

It’s the most common mistake: looking for one rule that applies to all boots. There isn’t one, and sizing can even differ between two models from the same brand. Dr. Martens makes only whole UK sizes, so those who wear a half size generally go down to the nearest whole size. With UGG, the rule even differs between Classic and Tasman.

That’s why each brand has its own guide, which you’ll find in the size converter. If you’re unsure, measure your foot in centimetres and send us the measurement: it’s the only detail that stays the same from one brand to another.

How to care for them so they last

Smooth leather needs nourishing cream two or three times a season, not just once. Suede needs spray before its first wear and a rubber brush when it starts to look dull. Sheepskin should never be washed and should be brushed dry.

The rule that applies to everyone: never dry them near a radiator. The leather dries out, cracks and can't be restored. Remove the laces, stuff the boots with paper and leave them to dry away from heat, even if it takes two days.

With boots, trouser length matters as much as the boots themselves: either tuck them in or let them cover the boot shaft - anything in between doesn't work for anyone. Find suitable lengths and fits in the autumn-winter trousers guide.

Frequently asked questions

Which boots should you choose for winter 2026-2027?

It depends more on the weather than on style: if it rains often, choose waterproof leather boots; if the cold is dry, sheepskin; if you want something that will last ten years, choose a Goodyear-welted boot. A mid-heel ankle boot remains the most versatile choice for everyday wear in the city.

Can you wear UGG in the rain?

Better not. Sheepskin keeps your feet very warm but isn't waterproof: it's great in dry snow, but gets stained and damaged on wet pavement. For rainy winters, choose waterproof leather boots and save sheepskin for sunny days.

What size boots should you get?

There's no one-size-fits-all rule, and sizing also varies between models from the same brand: Dr. Martens only makes full UK sizes, while sizing varies between Classic and Tasman models from UGG. The one thing that never changes is your foot length in centimetres: measure it and compare it with the specific brand's size guide.

How long does it take to break in a boot?

One to two weeks of gradual wear, with thick socks and short distances at first. Softer leather versions - like Virginia leather on the Pascal models - are comfortable almost right away. You can't skip breaking them in: it lets the leather take the shape of your foot.

How do you dry wet boots?

Away from all sources of heat. Remove the laces and insoles, stuff the boots with absorbent paper, and let them dry at room temperature, even if it takes a couple of days. A radiator dries out the leather and causes irreversible cracking: the most common damage, and the hardest to repair.

When is the best time to buy boots?

Between September and October. Core sizes — 38 to 41 for women and 42 to 44 for men — sell out first, and the most sought-after styles aren’t restocked during the same season. By December, you’re choosing from what’s left.

For tops, the knitwear guide follows the same approach: start with how you’ll wear it, then choose the style.

For outerwear — coats, down jackets, parkas or bombers — there’s a guide of its own: how to choose by reading the filling and membrane details.

Editorial team at Vittorio Citro Boutique, Roccapiemonte. We’ve been selling fashion since 1917.