7 Types of Winter Boots for Men To Invest In

As the winter months close, it’s time to consider your footwear wardrobe. Ideally, a stylish gent has a couple of pairs of winter boots in rotation. You want comfortable, durable styles that keep your feet warm and dry while letting you stay as fashionable as ever. That way, you’re less likely to succumb to the dreary moods accompanying cold, harsh winter days. Think rugged waterproof boots, with lots of traction, so you don’t end up with soggy socks. You could also choose sleeker styles for milder days and dressier occasions such as the office or after-work drinks. Whatever you prefer, you also want to ensure they’re good quality. Below, we take you through the different types of winter boots for men that are worth investing in.

Types of Hiking Boots

Hiking Boots

You don’t need to be training for Mount Everest to wear hiking boots in the winter. The increase in popularity of utilitarian fashion means they’re much more stylish and commonplace than ever. Plus, by design, they’re an excellent option for facing all kinds of miserable weather while keeping you ever-so-comfortable and warm. They’re kind of the winter equivalent of trendy dad sneakers. Look for thick soles, sturdy ankle support, and cushioned lining and soles. Then, keep it modern, stylish, and not over-the-(mountain)top by choosing premium leather finishes. It’s a more rugged and casual style, so don’t chuck them on with your favorite suit. Instead, go for a lumber-snack vibe and opt for raw denim, flannel shirts, and cable-knit sweaters.

Brogue Boots

Gaelic farmers pioneered broguing as a practical way to drain swampy water from their shoes in the fields. However, nowadays, the holes are entirely decorative yet maintain that heritage feel. Brogue boots are an excellent smart-casual style for winter. As a general rule, you can wear them with the same kinds of clothes that you’d wear brogue shoes with. Match it with your wool suit for work, rock chinos, and a cable-knit sweater, or mix it up with a more rugged combination of rolled-up jeans, a white tee, and a bomber jacket. The same rules apply with brogue boots as shoes — the more holes, the more casual a style. Additionally, the darker the shade, the more formal the boot, so you can wear a black boot more dressily, while a tan one is best reserved for casual outfits.

Work Boots

Like hiking boots, work boots are a practical style that has successfully transitioned into the fashion world. While some features, such as steel caps, are less prevalent, others, such as padded ankles, plentiful cushioning, grippy soles, and waterproof finishes, remain. It’s everything you’d want in a comfortable, durable, warm winter boot. Timberland’s iconic Yellow Boot is one of the original styles that made its way into mainstream popularity. However, plenty of companies offer stylish work boots that can be worn in casual offices, on weekend adventures, or for Sunday sessions at the pub. Channel your inner Drake by rocking a pair of work boots with chino-style joggers and a hoodie. Alternatively, embrace an ‘I-work-on-a-ranch-in-the-Rockies’ vibe with selvage denim and a flannel shirt or cozy parka.

Chelsea Boots

If you only want to buy one pair of boots for winter, then the king of versatility, the Chelsea boot, should be your pick. The 19th-century design was originally an alternative to lace-up riding boots. Modern Chelsea boots look just as good with a suit as skinny jeans and a leather jacket. It’s the perfect all-rounder. Black is the most classic option; browns and tans are also great. For winter wear, avoid suede, as it’s more prone to water absorption and requires much more dedication to cleaning and care. Ideally, choose a pair with a rubber sole and good-quality elastic sides that won’t distort with regular use. A round toe is more flexible than a pointed one, and a good-quality brand will have a helpful pull tab.

Ankle Boots

Ankle boots are an elegant style and an excellent alternative to low-cut designs such as chukkas or sneakers. Look for classic cuts such as Jodhpur or monk-strap boots for the ultimate in-winter sophistication. These go well with wool trousers, a well-cut blazer for the office or chinos, and a pea coat for the weekends. Leather will offer the most durability and resilience and are easily polished to remove any signs of winter wear. If you can find options that have thicker rubber soles, that will give you more stability and traction in the wet.

Combat Boots

Combat boots have a long military history. From war trenches of Europe to the rice paddies of Vietnam, combat boots have always been a sturdy, hard-wearing style that still protects the feet of the modern-day armed forces. Of course, they’re also a fashion statement and the perfect choice for stylish gents looking for winter boots. The rubber soles with deep tread and reinforced leather uppers make them exceptionally durable. They also have a rough ‘don’t mess with me’ vibe, making them popular among the music scene’s punks, rockers, and metalheads. When it comes to styling, combat boots are versatile. Please keep it simple with jeans and a bomber jacket, or take a post-apocalyptic neo-sci-fi approach with a statement overcoat. Alternatively, if you’re feeling bold, take inspiration from London-based designer Charlie Casely-Hayford and contrast your combat boots with classic tailoring.

Chukka Boots

Another boot with military history is the chukka. While seeing them as a spring or fall boot is more common, they’re still an excellent winter option. They’re exceptionally versatile and suit most smart-casual and casual outfits. Rock them at the office with chinos, a button-down, and a bomber jacket, or on the weekends, with jeans, a field jacket, and a t-shirt. While suede is the most ubiquitous option, opting for smooth leather for winter is better. This will wear better and be much easier to maintain and keep clean. The cousin of the chukka, the desert boot, is also a great option because it has a crepe rubber sole that can provide extra traction.

What to look for in Winter Boots

Quality Materials

Winter boots can take an absolute beating over the cold months, especially when combined with rain, mud, snow, and salt. Consequently, if you want your shoes to last more than one season, investing in a quality product is best. The best winter boots are made with good quality, genuine leather. Look for full-grain hide that hasn’t been sanded and will have all its beautiful, natural imperfections. It’s also the most durable and naturally water-resistant. Plus, it adapts to the shape of your foot, molding it to an exceptionally comfortable fit. Avoid leather for soles, as it wears quickly and is less suitable for slippery and wet conditions. Rubber is the most appropriate choice, as it has a lot of waterproof grip. Technology has come a long way, though, and rubber soles don’t necessarily mean they have to be big and chunky.

Practicality

You want to make sure you’re mixing both form and function for your winter boots. While you may only wear your boots around town or to the pub, you still want them to be practical. Rubber soles are the best options for staying surefooted. Of course, you can opt for a chunky sole with lots of tread. However, many manufacturers recognize the need for more slimline options and have released suitable alternatives. If you live somewhere considerably wet and snowy, you’ll also want water and snow-proof options with warm lining to keep your toes toasty.

Goodyear-Welted Soles

Goodyear-welting is often considered the gold standard of shoe construction. It’s brilliant because it stitches the upper and soles together using a rib-like strip of leather or canvas. This has many benefits, especially for winter boots. Repairs are much easier because the sole can be removed without damaging the upper. Goodyear-welted shoes are also the most waterproof, as there’s no avenue for moisture from the ground to get up through the sole. Finally, they’re also really comfortable because the middle is filled with a cushioning component like a cork. Of course, every shoe construction type has cons as well. These soles can be less flexible, take longer to wear in, and tend to be more expensive. Spot this type of welting by checking the shoe’s sole for a line of stitching which matches stitching on the top around the welt (or lip).
 

Alex Linde

Writer | Website

Alexandra Linde is an experienced writer holding a bachelor's degree in Journalism. She is the owner of Alexandra McKiterick Creative and has expertise in travel, fashion, fitness and lifestyle. Alex has previously written for Flightcenter, Travello, and Backpacker Deals.