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

How to wear · Men’s shoes

Men’s winter shoes should be chosen for the weather, not the calendar. If it rains often, you need a leather boot described as waterproof, with sealed seams. In dry cold, the lining matters: wool or sheepskin. For the office, a leather derby or Chelsea boot with a rubber sole is best, because leather slips on wet sidewalks. For the weekend, choose a combat boot or suede chukka.

Here, we’ve sorted them by situation, with the features listed on the product pages for the styles in our boutique and the size to choose for each brand. Find the full selection among our 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 heat-sealed. Water-repellent means the surface sheds droplets for a while, then gives way. The sheepskin in Classic UGG boots, for example, is pretreated to be water-repellent: it can handle a splash, not an afternoon of rain.

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

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 sheepskin is the warmest of all and the most delicate when it comes to water. A leather lining doesn’t provide warmth; it lets your foot breathe. It’s the right choice for eight hours in a heated office.

1. Rain: the waterproof boot

It’s the pair for walking, taking the train, or riding a scooter. The Timberland Premium 6-Inch features a Premium Timberland leather upper, sealed seams, 400 grams of PrimaLoft insulation, and a steel shank under the arch. These are the details listed on the product page, and they explain why customers come back for the same model when their first pair wears out. Find it in our Timberland men’s selection, in yellow and black.

If yellow feels too worksite, the Heritage 6-Inch Waterproof offers the same stated features (waterproof leather, 400-gram PrimaLoft, anti-fatigue footbed) with brogue stitching, in wine. It doesn't look like a work boot with chinos and a wool coat.

2. Dry cold: wool and sheepskin inside the shoe

On cold, dry days, with a northerly wind and clear skies, lining matters more than water protection. The UGG Neumel is the answer for men who don't want a bulky boot: low profile, with 17-millimeter UGGplush lining and insole. The black Neumel Chelsea, with twin gores, looks like any Chelsea boot under dark jeans; the chestnut suede lace-up Neumel is more casual.

If you want genuine sheepskin, there's the men's Classic Ultra Mini, with a short shaft and no laces. Without animal fur, there's the Panchic P001 suede ankle boot, lined with faux fur. The limitation applies to all three: they're shoes for cold, dry weather, and on wet asphalt the suede stains and the sheepskin gets soaked. Find them on the UGG men's page and among the men's ankle boots.

3. Light snow and gravel: the boot

For a weekend in the mountains, a village inland, or icy mornings, you need a grippy sole and ankle coverage. The most versatile men's winter boot we carry is the Timberland Premium with PrimaLoft, waterproof with a padded leather collar. The Euro Hiker is lighter, with an EVA midsole and molded rubber outsole, and walks almost like a sneaker; however, it isn't described as waterproof, while the Premium is.

More urban, the Premiata MidTreck 507: black, trekking hooks, Vibram sole. One 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

Men's boots, ankle boots, and lace-ups for winter

Dr. Martens1460 Smooth combat bootsTIMBERLANDTimberland Premium 6-Inch waterproof boots for menDoucal'SMen's suede Derby lace-up shoes in TerreSEBAGOSebago Tala suede ankle boots with EVA soleTIMBERLANDTimberland Heritage 6-Inch waterproof beef boots for menDoucal'SMen's suede lace-up shoes with hooksDoucal'SMen's suede lace-up desert bootsTIMBERLANDTimberland Britton Drive leather boots for men with PrimaLoft®

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

This is where people most often go wrong, because office shoes traditionally come with 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 Barrett polished-black-leather brogue is the clearest example: a wingtip, leather lining and a lugged rubber sole. It’s a derby with a commando sole, and works with a grey suit. Barrett has been making shoes since 1917, the same year our family began selling them. The Doucal's suede derby shoes, in earthy or mahogany tones with hooks, have Blake construction and ultra-lightweight rubber soles: softer and less formal.

If you prefer ankle boots, there are the black leather Doucal's Beatles with rubber soles, made in Italy, and the Fabi Wembley Chelsea boots. The UGG Loften chukka boots, in oiled full-grain leather with 10 mm UGGplush lining, are for anyone whose feet are always cold and whose dress code is smart casual. The rest is in our men’s lace-up shoes and Doucal's selection.

5. The combat boot that works almost every time

The eight-eyelet Dr. Martens 1460 has a Goodyear welt, an air-cushioned sole and an upper that moulds to the foot after breaking in. It works with jeans, cargo trousers and, with the right trouser length, even a suit jacket. The brown pebbled-leather Pascal Ambassador is softer from the start; the 2976 is the Chelsea version, without laces.

Dr. Martens does not claim these models are waterproof: they handle city rain well with a coat of leather balm, but for walking for an hour in the rain, Timberland is still the choice. The break-in period lasts a couple of weeks, and we’ve put together a guide on how to choose combat boots. Men’s styles are in the men’s Dr. Martens collection.

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

Saturday calls for the opposite of office wear: suede is an option, weather permitting. The Sebago Tala is an oiled suede chukka boot with leather laces and an EVA sole; the Wilson by the same brand has Blake construction and a leather sole with a rubber outsole. The blue suede Doucal's desert boot, with its 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 and feature a Vibram Vi-Lite sole. The UGG Lowmel sneakers have UGGplush lining and insoles, but also a mesh vamp: warm, but not suitable for rain. Find the others among our 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 thick socks. Here 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, runs true to size. Find conversions and more details in the Timberland size guide.

Dr. Martens are available only in whole sizes. If you wear a whole size, choose your usual size; if you're between sizes, go down to the nearest whole size, as the leather gives with wear. Find more details in the Dr. Martens size guide.

UGG: for the Neumel, the guide recommends your usual size, or half a size up if you have wide feet; for the Classic Ultra Mini, choose the smaller size if you're between sizes, as the wool compresses. Find all the details, model by model, in how UGGs fit. Doucal's states that its fit is generous, but the adjustment varies by model: each product page includes a fit note, which is worth reading.

If in doubt, measure your feet 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 each season: Dr. Martens recommends on its product pages cleaning with a damp cloth, letting the shoes dry, then applying balm. Protect suede with waterproofing spray before wearing it for the first time, and brush it when it starts to look dull. Brush sheepskin dry.

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

Frequently asked questions

Which men’s winter shoes can withstand the rain?

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

In winter, is a leather or rubber sole better?

Rubber, if you’ll be walking. Wet leather soles are slippery on marble and steps, and wear out quickly. Many derby shoes and dress lace-ups have rubber soles, even lug soles, and work well with a suit; leather soles are best for dry days and formal occasions.

Can suede shoes be worn in winter?

Yes, in dry weather and after treating them with a waterproofing spray before wearing them for the first time. In heavy rain, suede stains and stiffens; for wet days, smooth leather or a boot specifically described as waterproof is a better choice.

Can men’s UGGs be worn in the rain?

It’s best not to. The sheepskin in 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 choose 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 available only 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, wearing the thick socks you’ll use in winter.

How should you dry wet shoes?

Keep them 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 irreversible cracking.

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