12 Handsome Dress Boots in Every Budget to Upgrade Your Footwear (2024)

They say that fine wine gets better with age. The same can be said for a great leather boot. Available in 11 colors and made with 100% leather, you will want to keep the Captain lace-up boot within arms reach for years to come.

A pair of well-made Chelsea dress boots can be a foundational yet elegant part of your evening wardrobe. Charles Tyrwhitt's design features smooth leather, a Goodyear welted construction, a comfortable rubber sole, and a pull tab for on-and-off ease.

Most chukka boots look too casual or rugged, as if they only belong in Once Upon A Time in the West. These don’t. In fact, crafted in luxe leather with a minimalist welted design, these look refined, elevated, and effortless to pull off under blazers and dress trousers (though they're still tough enough to be worn under a trucker jacket and jeans).

This handsome design from Spanish shoemaker Magnanni will instantly upgrade your daytime outfit with rich, burnished calfskin leather and a streamlined Chelsea profile, while a cushioned, arch-support footbed offers all-day comfort. The Diversa comfort tech promotes breathability, as well.

Known for their durability and versatility, owning a pair of suede Clark Desert Boots should be a no-brainer. Available in a variety of colors, have fun mixing-and-matching with your casual office looks, or pack a more neutral color (white or taupe) on your next vacation.

Characterized by a single line of stitching and broguing along the toe, Balmoral Boots were originally made for England’s royal family. Nowadays, they carry style cred for us commoners like this version from Beckett Simonon made with full-grain calfskin leather that only gets more stunning with age.

If you're looking to elevate your footwear game but aren’t ready to commit to a full-on dress boot, the newly re-designed OriginalGrand Chukka boot by Cole Haan might be a great start. The elegant leather upper is expertly balanced with a sporty, ribbed midsole, offering a casual start to your dress boot journey.

Like a pair of classic jeans, the ankle boot is one of those tried-and-true footwear staples that never go out of style. This sleek and contemporary design by Bruno Marc is easily within reach and available in a rich black as well as some colorful brown hue, with an easy-to-wear build.

If you think that the classic wingtip design is only reserved for oxford shoes, think again. The XC Flex Cody dons that sharp heritage wingtip accent that every man should own in their shoe collection, and a construction that's not only shock-absorbing but also flexible for all-day wearing comfort.

Suede boots might be considered the more casual alternative to leather, but when styled correctly, they can still elevate your outfit. Opt for a darker brown color to start (for greater versatility) like this design from Shoe The Bear that features a Chelsea form, an easy slip-on style, and twin elastic gores for an ideal fit.

If you live somewhere that frequently rains or snows, your boot wear might need additional protection. Check out this elements-ready Nisolo design made with waterproof leather, a hardwearing outsole, and a removable memory foam insole for enhanced comfort.

If you want to earn some serious style points and add an inch at the same time, easily slip into this zipper style in a timeless profile that can be dressed up with a wedding fit as well as down with casual attire and jeans.

Our editors at Men’s Health have put on a number of men’s dress boots and put them to the test on different occasions. To review the best dress boots for men, we’ve evaluated them based on style, comfort, price point, and durability. In addition, we also considered top-reviewed dress boots with high ratings on e-commerce websites we trust.

Saint Laurent practically invented the Western-meets-luxury boot category and honestly, we aren’t mad about it. If you want to earn some serious style points, and add an inch at the same time, slip into the Wyatt 40 style with soft almond toe, rich calf leather, and ankle harness.