Men's winter Shoes: which ones withstand rain, cold, and the office

How to wear · Shoes for men

Choose men's winter shoes based on the weather, not the calendar. If it rains often, you need a leather boot specified as waterproof, with sealed seams. In dry cold, the lining matters, whether wool or shearling. For the office, a leather derby or Chelsea boot with a rubber sole is the best choice, because leather soles slip on wet pavements. For the weekend, choose combat boots or suede chukka boots.

Here you'll find them grouped by situation, with the details listed on the product pages for the styles we carry in our boutique and the size to choose for each brand. Explore the full selection of men's boots; if you're looking for runway inspiration, see our guide to the season's shoe trends.

Three words to look for on the product page

Waterproof and water-repellent are not synonyms. Waterproof means water can't get in: treated leather and sealed seams, which Timberland calls welded. Water-repellent means the surface sheds droplets for a while, then gives way. The shearling on Classic UGG boots, for example, is pretreated to repel water: it can handle a splash, not an afternoon in the rain.

The second is the sole. Rubber with a deep tread, lugged or Vibram, grips on wet surfaces and insulates against cold ground. L'EVA is lightweight and comfortable, but offers less grip than rubber on wet surfaces. Leather is beautiful, but in winter it's the wrong choice for anyone who walks.

The third is the lining. PrimaLoft is a synthetic insulation designed to keep you warm even when it gets damp; UGGplush is a fabric made from recycled wool and lyocell; genuine shearling is the warmest of all and the most delicate in water. A leather lining doesn't provide warmth; it lets your foot breathe: the right choice for eight hours in a heated office.

1. Rain: the waterproof boot

This is the pair for anyone who walks, takes the train or rides a scooter. The Timberland Premium 6-Inch has an upper in Premium Timberland leather, seam-sealed construction, 400 g of PrimaLoft insulation and a steel shank under the arch. These are the listed features, and they explain why customers who buy them come back for the same model when their first pair wears out. Find it in the Timberland men’s selection, in yellow and black.

If yellow feels too much like workwear, the Heritage 6-Inch Waterproof offers the same listed features (waterproof leather, 400 g PrimaLoft, anti-fatigue footbed) with brogue stitching, in wine red. With chinos and a wool coat, it doesn’t look like a heavy boot.

2. Dry cold: wool and sheepskin inside the boot

On cold, dry days, with the north wind blowing and clear skies, lining matters more than water protection. The UGG Neumel is the answer for men who don’t want a bulky boot: a low profile, with 17 mm UGGplush lining and insole. The black Neumel Chelsea, with its double elastic gussets, looks like any Chelsea boot under dark jeans; the lace-up Neumel in chestnut suede is more casual.

If you want genuine sheepskin, the men’s Classic Ultra Mini has a short shaft and no laces. For an animal-fur-free option, there’s the suede Panchic P001 chukka boot, lined with faux fur. The limitation applies to all three: they’re made for cold, dry weather, and wet pavement can stain the suede and soak the sheepskin. Find them on the UGG men’s page and among the men’s ankle boots.

3. Light snow and gravel: the ankle boot

For a weekend in the mountains, an inland village, or icy mornings, you need a sole with grip and a covered ankle. The most versatile men's winter hiking boot we offer is the Timberland Premium with PrimaLoft, waterproof and featuring a padded leather collar. The L'Euro Hiker is lighter, with an EVA midsole and preformed rubber outsole, and walks almost like a sneaker; however, it is not listed as waterproof, while the Premium is.

More urban, the Premiata MidTreck 507: black, trekking hooks, Vibram sole. An honest note: for deep snow, none of these replaces a snow boot. These are shoes for city snow, the kind that lasts two days and then turns to slush.

Available now

Boots, ankle boots and men's lace-ups for winter

Dr. MartensCombat boots 1460 SmoothTIMBERLANDBoots waterproof men's Timberland Premium 6-InchDoucal'SShoes Lace-ups Men Derby in Terre SuedeSEBAGOSebago Tala suede ankle boot with EVA soleTIMBERLANDMen's Timberland Heritage 6-Inch waterproof Beef boot Men TimberlandBarrettBrogue shoe Men in dark brown suedeDoucal'SDesert boot Men in suede with brogue detailingTIMBERLANDMen's Britton Drive leather boot with PrimaLoft® Men Timberland

4. Office: derbies and Chelsea boots, but with rubber soles

This is where people most often go wrong, because office shoes traditionally have leather soles. In winter, leather gets wet, slips on marble steps and wears down quickly. You don’t have to give up elegant shoes: just choose a pair with rubber soles.

The black polished leather brogue by Barrett is the clearest example: wingtip detailing, leather lining and a rugged lugged rubber sole. It’s a derby with a commando sole, and it works with a grey suit. Barrett has been making shoes since 1917, the same year our family began selling them. The Doucal's suede derbies, in earth or mahogany tones with hooks, have Blake construction and ultra-light rubber soles: softer and less formal.

For those who prefer ankle boots, there are Doucal's Beatles in black leather with rubber soles, made in Italy, and the Wembley Chelsea boot by Fabi. The Loften chukka by UGG, in oiled full-grain leather with 10 mm UGGplush lining, is for those whose feet are always cold and who have a smart-casual dress code. For more options, explore our men’s lace-up shoes and Doucal's selection.

5. Lace-up boots that work almost all the time

The Dr. Martens 1460 eight-eye boot has a Goodyear welt, an air-cushioned sole and an upper that molds to your foot after breaking in. Wear it with jeans, cargo trousers and, if your trousers are the right length, even with a blazer. The Pascal Ambassador version in brown pebbled leather feels softer from the start; the 2976 is the lace-free Chelsea version.

Dr. Martens doesn’t claim these models are waterproof: they hold up well in city rain with a coat of leather balm, but for an hour-long walk in the rain, the Timberland is still the better choice. The break-in period lasts a couple of weeks, and we’ve dedicated a guide to how to choose combat boots. The men’s styles are in the Dr. Martens men’s collection.

6. The weekend: chukka boots, desert boots and winter sneakers

On Saturdays, the rule is the opposite of the office: you can wear suede, weather permitting. The Sebago Tala is a suede chukka boot treated with oils, with leather laces and an EVA sole; the Wilson from the same brand has Blake construction and a leather sole with a rubber forepart. The blue suede Doucal's desert boot, with a rubber sole, is the cleanest of the three.

For winter sneakers, the rule is simple: leather or suede, never canvas, and a proper sole. The Woolrich Classic Court sneakers are made in Italy from tumbled leather, with a Vibram Vi-Lite sole. The UGG Lowmel sneakers have UGGplush lining and insoles, as well as a mesh vamp: warm, but not for rainy weather. See the others among the men’s sneakers.

Sizing: every brand has its own rules

Boot sizes are easier to get wrong than sneaker sizes, because in winter you wear thicker socks. These are the rules from our guides, brand by brand.

Timberland: the 6-Inch boots run large, so if you’re between sizes, choose the smaller one; the Euro Hiker, designed for technical socks, fits true to size. See size conversions and details in the Timberland size guide.

Dr. Martens is available only in whole sizes. If you wear a whole size, choose your usual size; if you wear a half size, go down to the nearest whole size, as the leather gives with wear. This is explained in the Dr. Martens size guide Dr. Martens.

UGG: for the Neumel, the product description recommends your usual size, or half a size up if you have wide feet; for the Classic Ultra Mini, choose the smaller size if between sizes, because the wool compresses. Find details for each model in how UGG fit. Doucal's states that its shoes have a roomy fit, but the adjustment varies by model: you’ll find fit notes on each product page, which are worth reading.

If you’re unsure, measure your foot in centimeters in the evening, wearing the socks you’ll use, and send us the measurement. Size charts for all brands are in the size converter.

How to make them last until next winter

Smooth leather needs cream or balm a few times a season: Dr. Martens recommends in its product descriptions cleaning with a damp cloth, letting the shoes dry, then applying balm. Protect suede with waterproofing spray before the first wear and brush it when it starts to look dull. Brush sheepskin dry.

The rule that applies to all of them: never dry wet shoes on a radiator. Remove the laces and insole, stuff the shoes with paper, and leave them at room temperature, even if it takes two days. Direct heat dries out the leather and makes it crack, and that damage can’t be repaired.

Frequently asked questions

Which men’s winter shoes can handle the rain?

Those specifically described as waterproof, with treated leather and sealed seams, such as the Timberland Premium 6-Inch or Heritage 6-Inch Waterproof. Water-repellent isn’t enough: it sheds droplets for a while, then water gets through. A rubber sole with deep tread and ankle coverage also matter.

Are leather or rubber soles better in winter?

Rubber, if you’ll be walking. Wet leather slips on marble and steps and wears out quickly. Many derby shoes and elegant lace-ups have rubber soles, even lug soles, and work perfectly well with a suit; leather soles are best for dry days and ceremonies.

Can suede shoes be worn in winter?

Yes, in dry weather and after treating them with a waterproofing spray before first wear. Heavy rain can stain and stiffen suede; for wet days, smooth leather or a boot explicitly described as waterproof is a better choice.

Can men's UGG boots be worn in the rain?

It's best not to. The sheepskin on the Classic Ultra Mini is pre-treated to repel water, protecting against a few drops but not a full day of rain. Neumel and Ultra Mini are designed for dry cold weather; for wet conditions, you need a waterproof boot.

What size should you get in winter boots?

It depends on the brand. Timberland 6-Inch boots run large, so if you're between sizes, choose the smaller one; Dr. Martens are only available in whole sizes, so if you're between sizes, go down to the nearest whole size. In any case, it's best to try them on or measure your feet while wearing the thick socks you'll wear in winter.

How should you dry wet shoes?

Keep away from radiators and heaters. Remove the laces and insoles, stuff the shoes with absorbent paper, and leave them to dry at room temperature, replacing the paper when it becomes damp. Direct heat dries out the leather and causes it to crack irreversibly.

Editorial team Vittorio Citro Boutique, Roccapiemonte. Selling fashion since 1917.