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

Guide to the season · Autumn-winter 2026-2027

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

This is the guide by type, with what really works for each one. The complete selection is among women's boots and men's boots.

1. The combat boot, if the boot has to last ten years

Among women's combat boots, the eight-eyelet Dr. Martens 1460 is the benchmark: Goodyear welt, heat-sealed AirWair sole, and leather that moulds to the foot after breaking in and never goes back. It is the boot you 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 is the softest from the start and the right choice for anyone who does not want the usual break-in period. The combat boot works with denim, a skirt with visible socks and - surprisingly - tailored trousers, provided they are the right length.

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Combat boots and Dr. Martens

Dr. Martens1460 Smooth Combat BootsDr. MartensDr. Martens 1460 boots in pebbled leatherDr. MartensDr. Martens 1B99 tall boots in Virginia leather for womenDr. Martens1460 boot in Ambassador leatherDr. MartensJADON 3 platform boots in Pisa leatherDr. Martens1460 Pascal Virginia bootsDr. MartensSinclair leather platform bootsDr. Martens2976 leather Chelsea boots with platform

2. The waterproof boot, when it is really raining

This is the category in which we have the greatest depth, and that is no coincidence: the waterproof leather Timberland Premium 6-Inch is the best-selling model of the cold season, because it solves a problem instead of following a trend. Those who walk, take the train or take their children to school in the rain buy it again and again.

It is also available in the Stone Street with the platform, in camel suede, which adds a few centimetres of height and shifts the style from utilitarian to urban. One thing to note: waterproof suede still needs to be protected with spray; the leather’s water resistance does not protect the surface from stains.

3. Shearling, when the cold is dry

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

The limitation needs to be stated: shearling is not waterproof. It is perfectly fine on dry snow, but it deteriorates on wet asphalt. If your winter is more rainy than freezing, this is not the right category - or it should be reserved for sunny days.

4. The ankle boot you will actually wear

It is the style with the widest selection we carry, and for a practical reason: it fits under trousers without asking for anything, works from morning to evening, and does not dictate an outfit. The medium heel - five or six centimetres - is the height that will carry you through the whole day.

With an ankle boot, the critical point is the shaft: it must close around the ankle without squeezing and without leaving a gap where air can get in. If you have fuller calves, look for styles with side elastic or a long zip - it is the difference between a boot you can put on and one that stays in the box.

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The ankle boots we have now

Dr. Martens1460 Smooth Combat BootsTIMBERLANDTimberland Women's Stone Street Mid Platform BootTIMBERLANDStone Street Mid Warm Lined BootsASHASH Flare Ankle Boot in Dark Suede with Medium HeelASHFAME Women's Suede Leather Ankle Boot with 5 cm HeelUggUGG Classic Mini Heritage Suede and Shearling BootsASHASH Hasley Ankle Boot with Studded DetailsASHASH Flame Lily Moto Bootie Leather with Buckles

5. The Chelsea, the most underrated

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

It is also the only one that does not forgive the wrong size: without laces or buckles, the fit depends entirely on the elastic. If it slips at the first step, it will slip forever.

6. The après-ski boot that stopped being just for the mountains

The Moon Boot has moved beyond the ski resort and has been seen in cities for several seasons. They are the answer to the one situation in which everything else fails - deep snow and truly cold weather - and no one expects them to be elegant. There are only a few styles, and this category sells out quickly when the first cold weather arrives.

Sizing, with no single rule

It is the most common mistake: looking for one rule that applies to every boot. There is no such rule, and it can even vary between two styles from the same brand. Dr. Martens, which produces only whole UK sizes, generally means that those who wear a half size should go down to the nearest whole size. With UGG, the rule even differs between Classic and Tasman.

That is why we have a separate guide for every brand, which you can find in the size converter. If you are unsure, measure your foot in centimetres and send us that measurement: it is the only detail that does not vary from one brand to another.

How to care for them so they last

Smooth leather needs a nourishing cream two or three times a season, not once. Suede needs spray before its first outing and a rubber brush when it becomes dull. Shearling should never be washed and should be brushed dry.

The rule that applies to every pair: never dry them near a radiator. The leather dries out, cracks and cannot 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 boot itself: either the trousers go inside, or they fall over the boot and cover the shaft - the middle ground works for no one. The lengths and fits that work are in the autumn-winter trouser 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 a waterproof leather boot; if the cold is dry, shearling; if you want something that will last ten years, a Goodyear-welted combat boot. The mid-heel ankle boot remains the most versatile choice for everyday wear in the city.

Can UGGs be worn in the rain?

Better not. Shearling keeps you very warm but is not waterproof: it is perfect on dry snow, but on wet asphalt it stains and deteriorates. For rainy winters, a waterproof leather boot is the better choice, saving shearling for sunny days.

What size should you get in boots?

There is no rule that applies to everyone, and it also varies between models from the same brand: Dr. Martens produces only whole UK sizes, while the sizing correspondence for UGG varies between Classic and Tasman. The one measurement that never changes is foot length in centimetres: measure it and compare it with the specific brand’s size guide.

How long does it take to soften a combat boot?

Between one and two weeks of gradual wear, with a thick sock and short distances at first. The softer leather versions - such as the Virginia leather used for Pascal styles - are comfortable almost immediately. The break-in period cannot be skipped: it helps the leather take the shape of your foot.

How do you dry wet boots?

Keep them away from any heat source. Remove the laces and insole, fill them with absorbent paper and leave them to dry at room temperature, even if it takes a couple of days. A radiator dries out the leather and causes it to crack irreversibly: it is the most common and least repairable damage.

When is the best time to buy boots?

Between September and October. The core sizes - 38 to 41 for women and 42 to 44 for men - sell out first, and the most sought-after styles are not restocked during the same season. By December, you choose from what is left.

For the upper half, the knitwear guide follows the same principle: first the use, then the style.

For outerwear - coats, down jackets, parkas or bombers - there is a guide of its own: how to choose it by reading the filling and membrane.

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