7 Types of Boots for Winter (and How to Wear Them)

John Varvatos Fall 2015 Runway style animal print

Source: Vogue.com/John Varvatos

Marching into winter with a solid pair of boots (or five) on your feet is a surefire way to walk in style. Boots have a way of imparting an inherent yet trendsetting sense of sturdy masculinity, durability, and strength to any silhouette. Plus, they’re more protective and hard-wearing against wintry mixes.

However, one size doesn’t fit all when it comes to the almighty boot. And we certainly aren’t relying on the stereotypical cowboy boot to gallop through the cold weather. Although the sheer number of options can leave anyone with a few sole-searching questions, here we ensure your wardrobe is well-heeled with a boot for every occasion.

1. Chelsea

Source: Common Projects

Source: Common Projects

Borrowing their named from London’s trendy, cultural Chelsea neighborhood, the Chelsea boot really became part of the fashion lexicon in the 1960s when the Beatles wore them with their matching suits. Subtle yet statement-making, the elastic-sided shoe features a low heel, rounded toe, and an unadorned, streamlined construction. With a distinct mod vibe, the boots are best worn with a slim-fitting silhouette. Common Projects’s suede varieties are especially suave for fall. Skinny cuffed jeans and a fitted button-down shirt, or alternatively a contemporary take on one of those Abbey Road monochromatic suits, are both good pairings for the Chelsea. Add a fedora or wide-brim hat for another layer of style-forward flair.

2. Jodhpur

Source: Harris

Source: Harris

Often likened to the Chelsea, the Jodhpur features the same British-tinged flair but is differentiated by a wraparound buckle. The riding-inspired boots may be well-suited for a day at the races but they also can be relied upon to add a touch of refinement and polish to your daily uniform. These Harris dark brown burnished leather jodhpurs pack plenty of character that’s sure to elevate rolled-up jeans or skinny pants and a sport coat any day of the week. The buckle is a small detail, but it speaks volumes for this cross between casual and formal footwear.

3. Brogue

Source: Allen Edmonds

Source: Allen Edmonds

Broguing and voguing go hand in hand (or foot in foot) when it comes to this classically dapper style that are worthy of striking a pose. Much like their dress shoe counterpart, the brogue boots feature perforated detailing and a rounded silhouette that make them entirely appropriate for a suit. Of course, they work wonders for dressing up casual chinos and denim, too. Wingtip shaping provides another layer of elegant structure in the Dalton leather boots from Allen Edmonds.

4. Chukka

Source: Paul Smith

Source: Paul Smith

Sometimes referred to as a desert boot, the chukka is old-school and informal but not lacking in a sort of transitional charm. Ankle-height with two or three sets of eyelets, it is an ideal option for those looking for a cross between a shoe and a boot. The materials really dictate how to wear this one. For example, a camel suede version is best with denim or the military-casual khaki and brown route. For a slightly more dressed-up showing, go for a darker leather, which can certainly work for weekday office attire with chinos and a button-down. The rich claret hue in these Paul Smith “Morgan” boots is the perfect contrast for navy or charcoal-grey tailoring.

5. Combat

Source: John Varvatos

Source: John Varvatos

Primed for the ultimate fashion fight, combat boots are perhaps one of the more overt, aggressive ways to clad your feet. But this shoe move is worth the risk — especially when styled appropriately. Remember, just because your breaking out a pair of combats doesn’t mean you have to take the rest of your look into all-black, goth territory. Instead, pair the boots with a blazer, dress shirt, tie, and jeans and they immediately upgrade from angsty punk to an official dress boot — with an edge, natch. Or channel an urban streetwear vibe by leaving taller boots with a few eyelets unlaced at the top for a slouchier, cool look that’s perfect for joggers and an oversized knit sweater. The John Varvatos Six o’ Six convertible military boots are a classic, vintage-inspired option that’s plenty versatile.

6. Wedge

Source: Grenson

Source: Grenson

Most often defined by their soles made from a single piece of white, cushy rubber, wedge boots are workwear gone badass. Boasting a certain sense of toughness, this boot type is a study in contrasts. After all, when you combine rich leather dress boots with a white wedge sole, such as in these Grenson Fred V shoes, the result is nothing short of statement-making. They’re perfect to kick jeans and chinos into next-level territory. But, to really step outside the lines, pair them with rich textures like tailored tweeds and chunky sweaters for visual interest.

7. Hiking

Source: Viiberg

Source: Viiberg

You don’t have to hit the trails to trot out a good hiking boot. Designed for comfort and support, the wedge- or lug-sole shoes may have the reputation of being more functional than fashionable. But, thanks to the lumbersexual trend, their utilitarian style acceptance is growing — even amid the most urbane of gentleman. The heritage-inspired, woodsy soles, such as the Viberg chocolate-brown leather models, are ideal for casually rugged jeans-and-sweater weekends. And, if you are so inclined, the great outdoors awaits — and your feet are properly attired.

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