The Best Lace-Up Dress Boots To Upgrade Your Winter Wardrobe

Lace ’em up for an appealing blend of rugged refinement.

(HELM Boots)

This winter, your boot game needs an upgrade. Think of it like this: There’s a time and a place for traditional winter boots and galoshes (see: roaring blizzards), just as there’s a time and a place for refined winter dress boots.

There’s an art to selecting the proper pair of dress boots — the best ones call to mind something that Tommy Shelby might wear, rather than classic “Bean Boots” you’d lace up in a Nor’easter. A man’s footwear rotation needs both, since dress boots are built for the season’s more refined pursuits, like visits to cocktail bars and elegant winter parties. When the situation calls for layering up with a sleek topcoat rather than a winter parka, dress boots are the “next man up” in your wardrobe.

The best winter dress boots are also a fitting counterpoint to winter’s heavier textures, like tweed and wool trousers or corduroy pants (or even dark blue jeans). And stylish pairs abound at every price point, in plain-toe and wingtip designs, from accessible to splurge-worthy. It’s time to lace up in style with your favorite dress boots.

Shoe The Bear York Lace-Up Boots


Just as you embrace texture in your winter wardrobe, be it a fisherman sweater or tweed trousers, add a dash of that same visual appeal to your footwear. Textured black leather toes the line, pun intended between rugged and refined, while the slim toe shape makes these dress boots easy to style with patterned wool trousers and a navy blazer. $229.95

Thursday Boots Wingtip Boots

(Thursday Boots)

Wingtip boots, with their functional origins in the Scottish Highlands, are as fine an example of dress boots as any. The sturdy studded rubber outsole delivers standout traction, while the rich burnished leather pairs expertly with herringbone trousers and a wool sweater. $235

Charles Tyrwhitt Leather Brogue Boots

(Charles Tyrwhitt)

The casual ease of the chukka boot meets the durability of the traditional wingtip boot, while a flexible rubber sole provides grip without missing a beat. From the added traction to the ankle-height support to the distinctive Chestnut Brown color, these are a no-brainer for the office and beyond. $279

HELM Boots Zind Boots

(HELM Boots)

The plain-toe lace-up boot gets a dressy update via Austin-based HELM Boots. Consider these a perfect alternative to bulkier lace-up, plain-toe work boots, with a slimmed-down profile and elegant, burnished leather. Despite their sturdy construction, they’re still fit for wearing alongside tan chinos, navy corduroy pants or light grey wool dress trousers. $295

Allen Edmonds Park Avenue Captoe Dress Boots

(Allen Edmonds)

Classic black dress shoes shined to a blinding finish are always a reliable option, yet you can achieve that same refined look in a sturdy and streamlined pair of dress boots. Even James Bond himself has taken to wearing black dress boots with a navy suit, and it’s a style move you should steal this winter (especially when the pair in question comes from all-American footwear masters Allen Edmonds). $495

Tricker’s Stow Brogue Boots


You’ll see a common theme across the best dress boots, namely features like classic, dependable brogue detailing. It bridges the gap between rugged boots for the field and refined boots fit for the city, especially in a crisp black colorway. Burgundy trousers and a shawl cardigan are practically made for pairing with these heritage-quality British boots. $640

KINGSMAN + George Cleverley Pebble-Grain Leather Boots


The gentlemen of the KINGSMAN movie franchise blend secret agent style and fashionable performance, and these boots deliver in the real world, too. Cap-toe stitching adds another layer of dependability, while pebbled leather offers eye-catching texture. It doesn’t hurt that the rich Chocolate color calls to mind a dram of The Macallan on a cold winter night. $700

Grenson G1 Buckley Boots


Want a pair of real “stompers” when it comes to your dress boot rotation? These English-made, top-of-the-line boots blend the utility and appeal of combat or moto boots with a highly durable rubberized leather outer and a remarkably sturdy sole. We think Tommy Shelby would approve. $805