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10 Best Men’s Dress Boots You Should Be Wearing

Just because the cold weather has arrived, that doesn’t mean you can throw on any old pair of shoes. You still need to wear your suit to work, and it’s important to find a pair of dress boots that will both withstand the winter elements and work with your professional wardrobe. The best men’s dress boots can add a touch of style and refinement to an otherwise drab wardrobe, especially in the chilly and wet months when permanence and protection are necessary.

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Some things to consider when you’re combing through the options: style and material. The best and most durable boots are made with high-quality leather, which will provide both fashion-forward flair and ideal longevity to make sure your shoes last and look better with time. There are also many different styles to choose from, too, which mainly hinge on personal preference but will also vary based on whether you’re looking for more of a formal or casual appearance.

Whether you’re looking for a pair of tough boots to combat unpredictable weather patterns or you simply want to expand your work wardrobe with a pair of seasonally appropriate kicks, we’ve compiled a versatile list of the best men’s dress boots that pair great with everything from a two-piece suit to a button-down and premium denim jeans.

Harry’s of London Maddox Suede Boot

Harry's of London Maddox Suede Boot

Harry’s of London just released its fall footwear collection and the Maddox suede boots are one of our favorites. An elegant update to a classic Chelsea silhouette, the Maddox silhouette is offered in two colorways, features an extra stretch at the ankle that allows for more versatility when pairing with different fits, and the weatherproofed suede guarantees your feet will stay dry.

Allen Edmonds Williamsburg Chukka Boot

Allen Edmonds Williamsburg Chukka Boot

There isn’t too much to say about the Allen Edmonds chukka style Williamsburg boot except for the fact that they’re absolutely stunning. Boasting both a durable bench welt construction and a comfortable CustomCork insole, the soft-tan calfskin leather boot is equally at home dressed up with professional attire or dressed down with jeans.

Wolverine 1000 Mile Boot

Wolverine 1000 Mile Boot

The 1000 Mile Boot is Wolverine’s bread and butter. It’s a versatile boot available in six colorways, and every boot is backed with the guaranteed craftsmanship of the Wolverine brand that ages like fine wine. If you’re looking for a pair of boots with unbeatable quality and stark versatility, the 1000 Mile Boot is for you. The Wolverine x Vic Mensa collaboration also utilizes the 1000 Mile Boot silhouette, but it’s a more modern style that gives you the option to choose from three different heights and leather tans.

Thursday Boot Co. Captain Lace-Up Boot

Thursday Boot Company Captain Lace-Up Boot

The Thursday Boot Co. might be one of the most affordable options among the best men’s dress boots, but that doesn’t take anything from the boots when it comes to durability and function. Featuring a durable Goodyear welt construction, great-gripping rubber soles, and a water-resistant seal, the Captain lace-up boot offers a set of dry feet and comfortable, all-day wearing ability. The Thursday Boot Company also offers a super affordable, damn good-looking chukka style.

R.M. Williams Comfort Boot

R.M. Williams Comfort Boot

The R.M. Williams Comfort boot is exactly that: comfortable. Offered in an array of beautiful leather tans that are cut from a single piece for longevity, a sewn-welt, non-slip sole, and a padded poron innersole for a sure fit, this yearling leather Chelsea boot is versatile enough to be worn as a light and tough work boot or dressed up with some fancy digs.

Minnetonka Two-Button Hardsole Boot

Minnetonka Boot

This Minnetonka Boot might boast a quirky design, but if you’re a Quentin Tarantino movie buff, these classic moccasin boots were worn by actor Brad Pitt in Once Upon a Time … in Hollywood. Featuring soft suede leather upper and a comfortable padded insole, just like Minnetonka’s original released in 1969, you would definitely get away with wearing these with a casual Friday get-up or a unique suit, but you might want to stay away from wearing these to an important board meeting.

Steve Madden Gadrick Wood Boot

Steve Madden Chukka

Steve Madden has a history of vending classic silhouettes at an affordable price. The brand’s low-profile chukka boots follow suit, sporting a leather upper and a hand-cut denim lining that offers high-quality craftsmanship and a heap of style points for a fraction of the price.

Saint Laurent Lukas 40 Zip Boot

Saint Laurant Lukas 40 Zip Boot

If you’re looking to splurge on a new pair of dress boots, Saint Laurent’s Lukas boot should be on your radar. Handmade in Italy, the Lukas style is somewhere between a Chelsea boot and a cowboy boot design, featuring a Western-inspired upper construction and a tapered stacked heel that blends well with everything from fitted dress pants to a pair of premium denim jeans.

Blackstone QM23 Plain-Toe Boot

Blackstone QM23 Plain Toe

If you’re looking for pure, simplistic style and all-weather protection without breaking the bank, the Blackstone QM23 lace-up boot is a great middle-ground option. These plain-toed puppies feature a beautiful leather upper and a stylish crepe rubber sole that can be worn everywhere from the office to the job site, and then out to dinner with the family.

To Boot New York Carlton Boot

To Boot New York Amsterdam Boot

Our favorite pick among the best men’s dress boots has to be To Boot New York’s Carlton boot. Featuring tons of rugged outdoor style, the Carlton boot is crafted with soft, luxurious, and durable deerskin leather that may very well spoil your taste for other leathers. What we love most about the boot is the balance between versatility and comfort, as it’s equally perfect for wearing with casual and classy attire in any environment.

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