The Best Dress Boots

The Best Men’s Dress Boots to Wear This Season: 7 Pairs to Know

From lace-ups to pull-ons to the always classic Chelsea, these boots are the easiest way to step up your fall style game.

by Beau Hayhoe
Updated: 
Originally Published: 
3 mens dress boots featured on a navy blue backdrop

There’s no easier way to take an outfit from meh to man, I look good than a great pair of boots. While rugged work boots deserve acclaim — and space in your closet — we’re talking about the dressier kind: lace-up, zip-up, or pull-on boots that you can wear with chinos to the office or jeans on the weekend. They’re comfortable, durable, and the simplest way to up your style game. With the help of, say, a pair of Chelsea boots or a great-looking pair of lace-ups, an otherwise ordinary outfit becomes something much more. Boots with chinos? Boots with office wear? Boots with jeans and a henley? The combos work.

The best men’s dress boots have a lot going for them. They can be styled with jeans or subbed in for loafers. They’re strike the ideal balance between streamlined and bulky. And they have more in common with lace-up dress shoes. Think fine leather, rich, burnished colors, and details like wingtip perforations or ornate stitching. If you’re looking to up your dress boot game this season, here are our favorite new pairs — all of which are surprisingly affordable.

1000 Mile Cap-Toe Classic Boot by Wolverine

Glossy Horween leather and a double-stitched cap toe elevate Wolverine's classic kick-around boot. The Midwest is well represented by this 100-year-old company, but it's not shy about incorporating the best the world has to offer, including a Vibram heel attached via Goodyear welt construction, allowing it to be resoled over a lifetime.

$385
All Weather Andres Boot by Nisolo

A dress boot doesn't benefit you if it wilts under the slightest amount of wetness. Nashville's Nisolo took its popular trench boot and added a host of water-resistant features, including a hydro-shedding leather, a gusseted tongue, and a nonslip rubber heel.

$260
The Dean Dress Boots by Tecovas

For the nicer saloons in your life, The Dean by Tecovas spiffs up your slim, dark jeans or adds a snarl to any suit. Smooth calfskin leather and a trim, eight-inch silhouette keeps everything tidy, but with just the right amount of attitude. One of the newer Tecovas offerings, the brand has left the corral.

$255
Captain Boots by Thursday Boots

When we think of mens dress boots that are office-appropriate (and classed-up enough for date night), this is one of the first pairs that comes to mind. They’re made with a low-profile design that makes them easy to wear with jeans or chinos. They're also built with a studded rubber outsole for all-day traction, and the captoe detailing gives them an added touch of class. They punch well above their price point.

$199
Dev Chelsea Boots by Shoe The Bear

Office-ready dress boots for men take many different forms, including that of the on-trend yet classic Chelsea boot. First popularized by (arguably) a little band called The Beatles, Chelsea boots have stuck around the menswear lexicon for decades. These are a great offering, as they feature a sleek toe shape, are easy to slip into, and even easier to pair with tailored trousers or corduroy pants. The Tobacco Suede color is also quite a nice shade for early fall.

$160
XC Flex Cody Wingtip Boots by Johnston & Murphy

Wingtip detailing typically found on dress shoes is translated handsomely into a durable and versatile pair of boots here. The Cody Wingtips blend rich suede and leather accents with razor-sharp detailing and an ultra-comfortable, flexible sole.

$199
Dress Ankle Boots by Blundstone

Here’s another famously outdoor-minded boots brand that continues to evolve. Blundstone boots are more commonly found at music festivals or on hiking trails, but the beloved Aussie brand has slimmed down its classic pull-on boot style into a dressy silhouette for business casual offices. These black leather dress boots are sleek enough to wear in most daily office situations, and way more comfortable than you’d expect.

$240

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