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The 13 Best Men’s Dress Boots for Your 9-To-5 Wardrobe and Beyond

10 Best Men's Dress Boots

With winter here, it’s time to switch out your loafers for a more seasonal option, and we don’t mean any old shoes. We mean a pair of rugged, durable, and sharp dress boots. The nine-to-five footwear’s style and function allows for extra durability even in the face of the elements that come with the winter season. They’re perfect for formal events but is also capable of being paired with your favorite denim jeans for a nice casual look.

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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 show-stopping boot as part of the brand’s 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 into 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!

Clarks Men’s Tilden Top Fashion Boot

Clark’s footwear is known to be durable and long-lasting. 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-bottom shoes 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 colors, 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.

Tecovas The Cartwright

Who said cowboy boots can’t be dressy? The out-on-the-range look is a hot trend for leading men, after all.

Can You Wear Dress Boots with a Suit?

Believe us when we emphatically say that yes, you can wear dress boots with a suit. Leave the no-show socks and your sneakers at home, because dress boots are the way to go. The best dress boots for men, of course, are well beyond a pair of rugged work boots or hiking boots, made with a cleaner silhouette and premium materials. It’s the use of top-quality leather (often with more polish and shine) that gives boots an especially sharp and tailored feel.  Dress boots often have a slimmer profile that works well with slim trousers (they’re not bulky or bulbous, like work boots that you’d wear with chore pants).

Dress boots also wear well with suits in the colder months as a practical option, helping you navigate city streets in style thanks to their higher ankle cut and durable tread. Dress boots are also, quite simply, cool as heck, adding a bit of edge to tailored styles. Think of James Bond in Skyfall, zipping through London wearing men’s black dress boots, and you’ve got as fine an example as any of the power of the dress boot.

What Men’s Boots are in Style?

Just like any regular pair of work boots, there are certainly several types of boots that are in style at the moment. To us though, the best pair of boots is the one you’re currently wearing (or looking forward to wearing next). Men’s boots that are in style include sleek captoe boots or on-trend Chelsea boots, each of which you can wear with a suit or with business casual ensembles.

Classic chukka boots are also a timeless pick that never go out of style. And for the utmost in versatility, you can’t go wrong with a pair of American-made boots, specifically plain toe boots (like the Wolverine 1000 Mile Boots) to wear with your finest threads. As we said before, the most stylish pair of boots could be the ones you’re wearing now.

What are the Most Comfortable Dress Boots?

Each of our picks for the best dress boots hit sthe right notes when it comes to toeing the line between comfort, form, and function. After all, a pair of men’s casual dress boots aren’t worth their weight if they slow you down and hurt your feet. We’re of the opinion that a pair of dress boots like the Clarks Tilden Boots (shown above) are perhaps the most comfortable dress boots out there.

They blend a crisp black colorway — ideal for wearing with either a black or navy suit — with the construction, durability, and lightweight feel you’d expect from Clarks. Of course, it all comes down to personal preference, so you might prefer the soft suede and unique design of the Minnetonka Two-Button Hardsole Boots, which are undoubtedly the softest boots on this list. And to close things out the right way, there’s no denying that even the Wolverine 1000 Mile Boots, with their beautiful leather construction, can become a seriously comfortable pair of dress boots the more you wear ’em.

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