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The 13 Best Men’s Dress Boots in 2020

With winter swiftly approaching, it’s time to switch out your loafers for a more seasonal option — and no I don’t mean any old beat-up boots. The dress boot! Its versatility in style and function allows for extra durability even in the face of the elements that come with the winter season. These shoes are also a great footwear piece to always have in your closet, perfect for formal events but can also capable of being paired with your favorite denim jeans.

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Although dress boots can keep you warm (and stylish) during the cold and wet months, these boots were not made for skiing or severe weather. When looking into the right boot for you, you should take into account the material and the sole. The thicker the sole, the more durable for facing the elements. Below we rounded up some of the best dress boots from some of the best men’s online clothing stores that won’t make you sacrifice style for comfort this winter.

Bottega Veneta Lean Boots

Bottega Veneta debuted this showstopping boot apart of their F/W 2020 collection. Merging the classic western boot with the sleek aesthetic of the Chelsea boot to craft the perfect dress shoe for any formal occasion.

Saint Laurent Wyatt Suede Chelsea Boots

Saint Laurent knows how to do a dress boot, and the Wyatt has been a staple among many male fashion insiders. Notably considered “the Chelsea boot of all Chelsea boots” with a wide array of finishings and materials to fit every style and look.

Amiri Crepe Chelsea Boots

Debuting in Amiri’s new F/W 2020 season, this boot will be sure to capture attention when you step in the room.

ASOS DESIGN Stacked Heel Western Chelsea Boots

The Western Chelsea boot has been trending in the men’s footwear scene for the past couple of years and doesn’t seem to be retiring anytime soon. This is a great option at a great price point too!

ASOS DESIGN Chelsea Boots in Black Leather with Angular Sole

asos dress boot

An eye-catching option to the classic Chelsea Boot. You’ll definitely get a few compliments on this one. and wait till they hear the price point!

Clarks Men’s Tilden Top Fashion Boot

Clark’s footwear is known to be durable and last. With a rubber ribbed sole, they’ll also help keep you stable when facing the elements.

Calvin Klein Men’s Beck Leather Boot

If you aren’t set on the pointy-toe look, but love the modern design, this is the perfect boot for you! With a side zipper closure and a rounded square toe, you get both the modern touch and classic silhouette.

Anthony Veer Monroe Merino Wool Leather Dress Boot

Merino Wool? Yes, and we aren’t talking about sweaters — but this boot will definitely keep your feet warm like one.

Christian Louboutin Roadie Flat

Who said red bottoms are only for women? Men can get a taste of the luxury signature red bottom with these chic dress shoes. Crafted to add sophistication to your on- and off-duty looks.

Wolf & Shepard Chelsea Blitz

Water repellent suede … that’s all. A must-have in any men’s wardrobe to show off personal style and beat the weather odds.

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.

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 a 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.

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