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The 15 Best Dress Boots for Men to Wear in 2023

Photo: Wolverine Original 1000 Mile

It’s an unfortunate truth that we can’t wear slippers to formal events. The world just isn’t ready to reach that point of progressivism and sophistication yet. All kidding aside, we’re happy to have dress boots as a stylish, elegant, and in many cases, versatile alternative to cover our formal footwear needs. The dress boot is a critical component of any man’s wardrobe, despite many men taking a strictly utilitarian approach when shopping for them. A great pair of dress boots not only completes your wardrobe but also increases your style quotient, elevating an entire outfit.

The fashion industry is bursting at the seams with an almost incalculable amount of different dress boots, and while variety is the spice of life, having too much of it can make shopping a daunting task. It can be difficult to avoid the countless knock-offs, cheap pairs, and overhyped styles, but thankfully, you don’t need to worry about any of that. We have curated a list of our favorite dress boots from some of the best brands the industry has to offer. These are fifteen stylish, elegant, versatile, and durable offerings that are sure to turn heads in any formal setting you walk into, so have a look below to discover your next pair.

Clarks Tilden Top Boot

Starting our list is the Tilden Top Boot from Clarks, a staple in the footwear space for over a century. This boot thrives because it’s versatile enough for any occasion. Its classic silhouette features clean lines and a streamlined design, and a 100% premium leather construction. Moreover, it sports a durable TPR outsole that brings flexibility and shock-adsorption for enhanced comfort and support. The Tilden Top even has a removable Ortholite footbed and soft padding cushioning, which makes them all the better to wear for long events. Add in its affordable price tag and you have one of the best-valued dress boots on the market.

Purchase: $50+

Thursday Boot Co. Scout Chukka

Making a “best dress boot” list without the inclusion of a Thursday Boot Co. boot would be an act of boot blasphemy. In particular, their Scout Chukka is a dapper boot that alchemizes classic British style with rugged, American design to create a dress boot for virtually any occasion. This handsome Chukka features a durable leather Stitchout construction, fully-lined supple glove leather interior, Poron antimicrobial shock-absorbing insoles for added comfort, premium round waxed cotton laces, and studded rubber outsoles. Simply put, these boots are tough, stylish, and will last you years.

Purchase: $149

Allen Edmonds Williamsburg Chukka Boot

Allen Edmonds is a brand that needs no introduction. Their Williamsburg chukka is beautiful, elegant, and offers a minimalistic and formal silhouette. While simple in design, the attention to detail that went into making this boot is immediately apparent. It features a 360-degree Bench Welt construction for durability and stability, a single oak leather sole, and a CustomCork insole that makes this stylish offering as comfortable as it is beautiful. If you’re in the market for a classic-looking two-eyelet plain-toe boot, you can’t go wrong with this one.

Purchase: $200

Dr. Martens 101 Suede Boots

A footwear institution, Dr. Martens could easily fit on the Mount Rushmore of boots. Their 101 suede boots epitomize their design language while also sporting an elegant flair due to their use of soft, oiled suede. The boots’ lace-up front offers a nice textural contrast atop their streamlined silhouette, while their signature AirWair bouncing soles with reinforced yellow stitching pop under the gorgeous all-black design. This is the type of boot that is so stylish you almost feel sorry for wearing it.

Purchase: $230

Beckett Simon Elliot Balmoral Boots

The Beckett Simon brand has been around since the 1800s for good reason, as their boots are stylish, elegant, and impeccably made. This classic Balmoral number features an Oxford-adjacent design due to its closed lacing system and the subtle row of hand-punched broguing near the toe cap. The boots are formal, elegant, and comfortable, featuring Vachetta leather lining to allow your feet to breathe easier, a durable rubber sole for better grip and shock absorption, and an Italian leather construction that will age like a fine wine.

Purchase: $239

Ted Baker Andrrew

If you’re looking for a designer to help up your style quotient without having to pay an arm and a leg, then Ted Baker is right for you. The Andrrew leather boot has a gorgeous silhouette and a derby style design, with a gorgeous stitching pattern and beautiful broguing throughout. It’s made of pure leather with a leather lining and a vulcanized rubber outsole, making this a wonderful statement piece you can wear.

Purchase: $276

Red Wing Iron Ranger in Black

For those wanting to toe the line between rugged masculinity and elegant design, we suggest Red Wing’s Iron Rangers. They offer a tough military build, yet their stitching and clean design give them a formal feel. These American-made boots feature a lace-up front, a full-grain, oiled leather construction, and a Vibram 430 mini-lug outsole. For added flair, the boots’ nickel eyelets and hooks and white stitching offer some great visual contrast against the smooth, black upper.

Purchase: $350

Wolverine Original 1000 Mile Boot

A certified blast from the past, the Wolverine Original 1000 Mile boot was modeled after the original 1914 pattern. Its upper is made from premium Horween Leather, which comes from one of the oldest, most revered US tanneries in existence, and it also features a Goodyear Welt construction, which adds durability and longevity to this handsome-looking shoe. This icon may be best known as a work boot, but it’s plenty spiffy enough to be dressed up for semi-formal occasions. Like many entries on this list, the Wolverine Original 1000 Mile Boot is made to last and only looks better as it ages.

Purchase: $385

Alden x Todd Snyder Plain Toe Boot

It only makes sense that two juggernaut style brands working together would yield a phenomenal dress boot, which is exactly the case for the Alden x Todd Snyder Plain Toe Boot. These limited-edition hand-crafted boots take Alden’s already stellar plain toe boot and give them a dark, gorgeous chamois construction. They feature a 360-degree storm welt to keep out moisture and a natural plantation crepe outsole for durability. Those looking for trendy boots that are understated yet head-turningly cool should absolutely add these to their wardrobe.

Purchase: $593

Alden Shoes Men’s Straight Tip Boot

A modern-day dress boot for the modern-day man, the Alden Straight Tip Cap Toe boot is a sharp offering that elevates any wardrobe with which it’s paired. It boasts a sleek and simple design with a tall, elegant silhouette that you can wear in virtually any setting. The boots feature a calfskin leather construction, a 270-degree Goodyear welt, and a layer of cork under the insole to enhance durability and insulation. For added quality and stability, the boot even has a tempered steel shank that’s precisely contoured and triple ribbed — definitely not something you see every day in dress boots.

Purchase: $595

Cheaney & Sons Hanover Balmoral Boot

It’s almost a crime that Cheaney & Sons’ Hanover Balmoral Boot can’t be seen at eye level. The boot’s name commands respect and connotes class while its silhouette provides an elegant vibe, all packaged in a confident, burgundy calf leather construction. These luxe boots sport a distinctive navy leather lining, in-channel stitched oak bark leather soles with a hand-painted fiddle waist, and oak bark soles. They’re sophisticated, gorgeous, made-to-last, and will stop traffic wherever you wear them.

Purchase: $610

Tricker’s Stow Boots

Sporting an ankle-length profile and a silhouette that’s equal parts elegant and rugged, Tricker’s Stow Boots are a jack-of-all-trades choice. In terms of style and versatility, these boots concede nothing with an intricate broguing pattern throughout the boot that provides visual and textural contrast against the boot’s smooth full-grain leather construction. They’re handcrafted in the brand’s Northampton workshop and stitched to sturdy and reliable Dainite rubber soles, which offer excellent traction while also helping to ensure that this stylish offering lasts for years.

Purchase: $640

Crockett & Jones Kew

An unforgivably stylish dress boot from one of James Bond’s favorite brands, Crockett & Jones’ Kew chukka boot is nothing less than stunning. Its willow grain finish provides a level of class and sophistication that’s unrivaled by its competitors, while the full-grain leather and “city” rubber sole give the Kew a dimension of durability and stability. One look at the gorgeous texture of the Kew and you know immediately that the detail and quality of care that went into making this boot was impeccable. We’d classify this boot as a wearable statement piece, full stop.

Purchase: $840

Brunello Cucinelli Waxed-Suede Chelsea Boots

Red-hot designer Brunello Cucinelli’s Chelsea boots feature a stone-wax suede construction, which enhances their durability and longevity while also looking the business. Their silhouette is streamlined, understated, and elegant, allowing you to wear them to a variety of places — which is good news because you are going to want to show these boots off everywhere. Throw in their elasticated gussets that bring enhanced comfort, and you’ll struggle to find a reason to ever take these dress boots off.

Purchase: $1,095

Tom Ford Croc-Effect Leather Chelsea Boots

Coming in loud and proud to finish our list are Tom Ford’s otherworldly Croc-Effect Leather Chelsea boots. For those looking to turn heads, drop jaws, and make a statement, these Chelseas are the perfect choice. They’re stamped with a croc-effect pattern, which evokes an eccentric and opulent feel to contrast the Chelsea’s classic understated silhouette. These boots thrive because they’re classy enough to wear to formal events while still being bold enough to wear in casual settings (for the right person, anyway). Regardless of where you need to wear Tom Ford’s Chelsea boots, you’ll for sure have the best boots in the room.

Purchase: $2,190

The Best Men's Suits Under $1,000

With all of these incredible dress boots you now have to choose from, check out our list of the best suits for under $1,000 to complete your classy ensemble.