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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.

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.

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.

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.

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.

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.

The fun thing about shopping for men’s boots is the fact that plenty of tried-and-true brands are now pushing themselves to make all sorts of different styles. Take Wolverine, long known for dependable work boots and the rugged 1000 Mile Collection. Their BLVD line is refined and yet every bit as well-made (and fairly priced) as the rest of the Michigan brand’s offerings. Take your pick from four handsome shades of leather, then wear these all fall.

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.

Florsheim has more than 100 years experience delivering dependable boots across the board. That expertise translates nicely into a pair of boots that sits right in the middle of the “rugged-refined” diagram, delivering plenty of office-ready style and comfort. They’ve used Horween Chromexcel leather (from the 116-year old tannery) to build a pair of cap toe boots that scream fall style.