The 8 Best Men's Dress Boots of 2019

Add some fresh style to your work wardrobe

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Dress boots can bring an extra touch of style to your usual professional wardrobe. They’re an especially good choice for the fall and winter months when the temperature drops and the weather becomes more unpredictable. You don’t need to go to a brick-and-mortar store to find the right pair of boots — instead, we’ve compiled a list of the best options available online, chosen to complement all kinds of wardrobes and personal styles.

When you’re shopping, keep an eye on the materials — most high-quality boots are made from leather, which holds up well over time and tends to look even better as it “breaks in” with frequent wear. This is what you should look for if you want something a little more rugged. Just make sure it’s still sleek enough for the office and doesn’t veer into full “work boot” territory.

Whether you’re looking for a boot silhouette to complement your work clothes, or you just need a tougher shoe for the winter months, read on for our list of the best picks for men’s dress boots available online.  

Best Overall: Dr. Martens Men’s 1460 Classic Boot

The classic Dr. Martens 1460 sets the standard for men’s dress boots. This brand traces its roots to 1960s England, and that original style, the 1460 boot, is still a top seller. These boots come in a range of colors and sizes and balance comfort, style, and value to claim our top spot.

Consider investing in Dr. Martens Unisex Wonder Balsam Shoe Polish to keep them in good shape. With the right care, these high-quality dress boots should last you a decade or more. You may enjoy them so much you want them in a few different colors to keep your wardrobe fresh!

Best Value: Bruno Marc Men’s Bergen Leather Lined Oxfords

If you want to balance cost with quality, Bruno Marc’s Bergen Leather Lined Oxfords are a great choice. These boots come in a range of colors and offer a wing-tip style in an ankle-height lace-up boot. Plus, they won’t break the bank. These boots feature an inside side zipper, so you won’t have to lace and unlace every time you want to take the boots on and off. A wooden heel adds a little more height and style to the boots.

It's worth noting that these are not true leather boots. They feature a faux leather upper body, which helps explain the value price with the great style. If you want boots for work, school, or out and around town, you won’t be disappointed with these classic style boots from Bruno Marc.

Best Classic Style: Red Wing Heritage Men’s Beckman Round 6” Boot

Red Wing Shoes is one of the most iconic American boot brands out there, using high-quality leather for their classic handcrafted styles. These boots are built to last for decades — the brand even offers specialized repair services in their retail shops to ensure a lasting product. 

Named for founder Charlie Beckman, the Beckman Round 6” boot features a beautiful, classic design that never goes out of style. Like all Red Wings, these shoes carry a premium price tag, but you can count on years of regular wear with proper care.

Best Chukka Style: Steve Madden Men’s Harken Chukka Boot

Steve Madden makes stylish footwear for both men and women, and the Steve Madden Men’s Harken Chukka Boot lives up to the quality you expect. These simple Chukkas offer a great design, come in four colors, and are versatile enough to wear at both work and social functions.

With these boots, you can easily transition from the office to a night on the town. If “business casual” is part of your weekly wear and you want an introductory dress boot, Steve Madden’s Chukkas are a fantastic starting point.

Best Minimalist Style: London Fog Mens Broadstreet Chukka Boot

If you're into clean, streamlined style, the London Fog Mens Broadstreet Chukka could be the dress boot for you. These boots come with a simple lace-up front and a sleek, traditional silhouette that works well with jeans, dress pants, or even a suit.

London Fog is a great brand for quality winter wear, and these faux-leather boots work well in all weather. They are comfortable and come in a range of colors from traditional browns and blacks to navy blue and green.

Best Slip-On: Giorgio Brutini Men’s Chelsea Dress Boot

These black leather boots from Giorgio Brutini combine style and simplicity in a sleek design that works both at the office and out on the town. They have a waxed leather finish and flexible side fabric sections that expand as you insert or remove your foot. The boot also features a handy loop at the top of the heel to help when sliding them on.

The majority of users say these boots fit as expected, but those with a very wide foot may find them to be a bit narrow. They are not the fanciest boots out there, but they should last a long time and are a great value for the price.

Best High-End: Thursday Boot Company Captain Men’s 6” Lace-up Boot

If you want executive-level comfort and quality, Thursday Boot Company offers the Captain (and similar President) men’s dress boot designs as the cream of the crop. These real leather boots look great, feel great, and are meant to last for years. You pay a premium for quality, but you get it all back in long-term value.

These lace-up boots feature high-quality leather, flat wax laces, and a cork footbed that is perfect for all-day use, even when you plan to spend hours on your feet. The studded rubber soles offer enhanced grip over a traditional sole. If you have the money to spend and have a high bar for quality when it comes to footwear, these boots are the way to go.

Best Western Style: Laredo Men’s 12-Inch Trucker Boot

Cowboy boots are definitely a statement piece, and they aren't exactly appropriate to wear in every situation. But some men prefer the look, comfort, and durability of these kinds of boots. If you're one of those guys, these boots from Laredo are a great choice.

The Laredo Trucker Boot features a synthetic sole and 12-inch shaft from the arch to the top of the boot. You’ll get an extra 1.5 inches of height with these classic western style boots, available in a range of colors. And if you wear them with a nice pair of pants, the Laredos' eye-catching leather designs are covered, leaving only the sleek lower part of the boot visible (and making them a bit more suited to cowboy-free occasions).