How to Pick a Pair of Winter Boots That Look Great With a Suit

Depending on where you live, you probably still have at least a couple months of cold or wet weather to look forward to before spring arrives. That means that if you don’t own them already, you’re going to need a pair of boots that can stand up to rain, snow, or slush — preferably ones that won’t look out of place when you need to wear them into the office.

Luckily, finding a pair of winter boots that fits the bill isn’t as difficult as you might expect. If you focus on finding a pair of boots that combine the right materials with a versatile style, you can get a lot of mileage out of a single pair of winter boots. Here’s our advice for finding the perfect pair of boots that’ll get you through the rainy, snowy, or slushy days to come.

1. Choose the right materials

Leather boots by O'Keeffe, Oak Street Bootmakers, and Thorogood

Source: Mr Porter and Nordstrom

When you’re shopping for a pair of boots that are going to get wet, you’re going to need to pay close attention to the materials used for both the upper and the sole. Look for a sturdy, grained leather upper that’s waxed or oiled for water resistance, but steer clear of a leather sole when you’re buying a boot specifically for wet weather. A Dainite sole is a great alternative since it’s a rubber sole that’s simultaneously hard-wearing and water-resistant while maintaining a trim silhouette (not like the hefty lug soles that you might associate with rubber). Another way to go is a commando sole, which is the clunkier style you probably associate with rubber soles. A commando sole offers better grip than Dainite in icy conditions. Keep in mind that if you find a boot that you love (and you’re confident in its water-resisting abilities), you can always have your cobbler swap out the sole for one more suited to winter weather.

A great boot with a Dainite sole is O’Keeffe’s split-toe leather boot, which is constructed of polished black leather that doesn’t even make it obvious that you’re wearing something water-resistant. If, on the other hand, you’re leaning more toward a traditional rubber sole, Thorogood’s American-made Dodgeville leather boots feature Goodyear-welted Vibram rubber soles, an excellent choice if you anticipate months of making an icy commute to the office. And if you’re simply looking for a solid leather boot and are open to replacing a leather sole with something a little better-suited to snowy winters, you can’t go wrong with the American-made trench boot from Oak Street Bootmakers.

2. Select an office-appropriate style

Winter boots by O'Keeffe, Ralph Lauren, and Ted Baker

Source: Mr Porter, Ralph Lauren, and Nordstrom

Choosing the right pair of boots can mean the difference between being embarrassed to trudge into the office with inappropriate boots on your feet and an extra pair of shoes in hand, or simply walking in from the cold, shaking the snow off, and going about your day wearing boots that work as well in the boardroom as they do on the street. Here’s where the shopping gets fun: You have several winter-friendly but office-appropriate styles to choose among, like a derby boot, a brogue boot, or a Chelsea boot. Derby boots are the best style for daily suit-wearers who work in formal offices, particularly in a rich and polished leather. Brogue boots are slightly less formal than an undecorated boot, but will look great with chinos and an oxford shirt at less formal offices. Chelsea boots are a British classic, and look as appropriate with a suit as with a pair of dark jeans and a chunky sweater (which means that they may become your go-to shoe on the weekends, as well).

If a derby boot sounds like the best option, consider a style like Grenson’s pebbled-leather boot, and consider swapping out the rubber sole for a less-obtrusive Dainite option. A classic brogue boot is O’Keeffe’s Algy boot, which is handmade in Italy with what Mr Porter aptly characterizes as “restrained but attractive” broguing. A slightly more budget-friendly option is Ted Baker’s wingtip boot, which is available in black or tan leather. And a great example of a hard-wearing yet polished Chelsea boot is the style from R.M. Williams, which is handmade in Australia and features chestnut-brown leather and low-profile but gripped rubber soles, or Ralph Lauren’s Belgrade chelsea boot in either black or dark brown leather.

3. Take care of your boots

Shoe trees by Church's and Tom Ford, shoe shine kit from Wolf

Source: Mr Porter

It sounds obvious, but once you’ve found a pair of boots that you love, it’s important to maintain them carefully, especially if you want them to stay water-resistant and continue looking great for the trek into the office. Make sure to keep them properly polished and conditioned, which will help prevent water from penetrating the leather. And if they do get soaked, whether thanks to a rogue rainstorm or an unfortunate encounter with a large amount of snow, make sure to let them dry out for at least a couple of days.

Always let your boots dry thoroughly on shoe trees, like Church’s wood and metal shoe trees or Tom Ford’s trees for lace-up shoes. Letting them air-dry naturally, not placed in front of a heater as you might be tempted to try, will help your boots maintain their shape and dry without unsightly creasing. And make sure to stock up on shoe polish and shoe brushes, like those in Wolf’s leather shoe shine kit.

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