15 Best Pairs of Dress Boots for Men Who Want to Look Extra Sharp

If you’re a proper menswear type of guy, this is as close to the term Dress Boot as you can get. Balmoral boots are cut like an oxford, with a closed lacing system. The only stitch that extends to the sole should be the toe cap, and you should get them in a high-gloss leather with a leather sole. It’s a modern interpretation of the semi-formal footwear you would’ve found in, like, the Edwardian era.

You, of course, can get bench-made versions of this type of boot, but you’d have to be a certain type of guy to go for that. For the average man who is shopping on a budget and looking for a properly formal boot, I think Beckett Simonon is a great value.

This, I’d call more of a derby boot, and once you get into this territory it starts to read less formal. Assuming you’re not going to an Edwardian-themed party, I’d say that’s a good thing. These can be worn with jeans or a suit and look at home. The rubber sole is comfortable and a touch rugged, but it doesn’t have the hardcore combat look of a lug sole. I think this is a great option for men who have been spoiled by a lifetime of wearing sneakers.

If you like brogue dress shoes, you’ll love brogue dress boots. Thursday Boot Company has a Goodyear-welted pair that looks oh-so chic when peeking out from beneath your pants. This style will take your jeans up a notch and round out your dress pants with a more stylish look. With cork footbeds, shock-absorbing insoles, and a hand-burnished effect, these boots are as timeless as your favorite wing-tip derbies.

Personally, though, I think this is the ideal dress boot for men. Call it a Chelsea boot. Call it a Beatle boot. Wear it with a dress heel or a Cuban heel. Something like this is where I’d send most guys, and I think it’s what most guys deem to be cool.

Aussie bootmaker R.M. Williams makes comfortable and stylish boots with some of the best leathers you can get without going bench made. The Craftsman is the model I’d recommend, because it reads more formal than the Gardener or Turnout. That’s because of the leather sole and chisel square toe. And when compared to lace up boots, I think a slip on, with its one-piece upper, takes less away from the suit you’re wearing.

That said, the problem with a pair of R.M. Williams boots is that they’re not actually formal, even though they’re supremely well made. I would take steps to hide the elastic ankle and pull tabs with a slightly wider hem and longer trouser. Do not wear skinny suit pants that tuck into the boot. Beyond that, I’m not a huge stickler for the rules, so I’d say you could wear them with a tux (so long as they get a good shine) for a rockstar thing.

OK, if we’re really going to dig into menswear rules, these are technically not dress boots. Lug sole, brogue design is casual in classic menswear. But those old rules have eroded. In modern times, this boot is plenty formal for almost all instance.

Tricker’s is a classic, near 200-year-old shoemaker from the shoemaker mecca of Northampton, England. Todd Snyder—a brand that has been on a roll as of late, a brand that can do no wrong—is killing it with stateside retail partners. These leather stow boots come in just under $800, which is actually a great price for British-made boots. I also love them in suede, especially that Todd Snyder green, though that admittedly takes it out of the dress realm.

While I’m breaking rules, let’s do another. Red Wings are definitely not traditional dress boots, but if you keep them well shined, they can easily pull double duty. The quality is incredible, and as you care for a pair of Iron Rangers, the shoes will take on a darker and darker patina, which helps them look dressier in my opinion. Get your cobbler to burnish them right before a party, and no one will tell the difference. Or, you’ll have a cool 1940s man back from war thing going on.

Normally, if you don’t want a boot with an elastic ankle, you’ll have to go with a zippered boot. But instead, I love a Jodhpur boot that uses a buckle to open up and fasten the shoe. It’s an old-school touch that makes a shoe read as more formal. There’s no elastic ankle to confuse you into thinking this is a work boot.

One of my favorite takes on the Jodhpur comes from Carmina. It’s simple, in a black box calf leather that has a fine grain and takes a shine incredibly well. Shine them when you want wear them with a suit; let them get scuffed up when you’re going through a few weeks of staying in jeans. I think this is the most versatile pair of boots on this list.

Carmina also makes a wonderful cordovan cap-toe dress boot. This boot has a military formal look that works really well with a suit.

Since I’m doing the double feature, how about some Carmina background? The brand is from Mallorca, a less traditional footwear-making center than some of these others, but it has the history and design chops to compete with the old British names. Its boots are competitively priced, but if you dig into the low-cut derbies and oxfords, you can find some great deals. At the moment, it’s one of my favorite places to look for footwear.

Yes, these dress shoes cost more than $500, but they’re such good quality that it’s actually a great deal. In fact, these may be the best value boots you can get from our list.

Grenson is one of the biggest names in British shoe making, and these Fred brogue boots show why. The shiny black leather boots have a super durable rubber sole, and its brogue details are stylish, even a bit peacockish. The boot’s construction is second to none.

If you have any knowledge of the current designer landscape, you’re aware of Thom Bronwe. The brand has always been singularly the brain child of the man himself, but now there’s Zegna money behind the machine, and the brand has (expectedly) blown up. Any red carpet is bound to have somebody wearing Thom Browne.

These stompy brogue boots are part of the look. Normally I think Thom Bronwe is a full look, like you wear it head to toe. I think these boots are actually really versatile. It’s an easy way to live in the Thom Browne universe without donning the skirt.

Now we have the cowboy answer. I would actually make the argument that the cowboy boot has reaches a greater audience within Americana that’s not strictly westernwear. I’m have no cow poke bonafides, but I wear a pair of cowboy boots literally every day. No one cares if you’ve ridden a horse or not. It’s just the most American choice of footwear.

And when you want Americana, you go to Lucchese. The brand still goes to great lengths to make boots in El Paso, Texas, and it has plenty of dress options in black or a dark brown, high shine goat or fancy exotic.

There’s a few ways a cowboy boot can fit into the dress category. First, keep it as simple as possible. This Knox skips the toe medallion you commonly find on cowboy boots for a more conservative presentation, and it’s full calfskin for a really luxe feel. Another option is to go high-shine, with something like the Gavin, whose santini goat leather can hold a tuxedo-level burnish. Lastly, you can lean into the western thing and go exotic. I prefer American alligator, but ostrich is a classic western choice; both look great when polished.

If you want a dress cowboy boot, but don’t want to pay Lucchese prices, you can make due with Tecovas. We write about Tecovas a lot… Just about once a year. (This year too.) Oh, and I talked to the design team a few weeks ago. The reason is the value proposition. You get Mexican made boots with good materials for a regular price under $500. It’s a good deal.

In the dress arena, I’d suggest the same game plan as with Lucchese. Go for high-shine or keep it black. These pictured are a snip toe, which is not on-trend in the westernwear world, but has a rockstar look that I consider to be timeless.

Back to lace-ups. RRL, the heritage-inspired wing of Ralph Lauren, makes some old-fashioned boots. These dark brown leather boots are the type of thing George Orwell talks about coveting in Down and Out in Paris and London. Except, well, they’re actually fancy.

As with anything RRL, these are made in the best factories in the world. For dress boots, that’s Northamptonshire, England. The only thing with these in the dress category is, again, they’re not all that dressy. They’ll smarten up a pair of jeans, and you can wear them with a suit, but they’re closer to a pair of derbys than a pair of oxfords.

Crockett & Jones is another truly classic British bench-made shoemaker; all its shoes are made entirely in Northampton, and the brand is still family-owned and operated. These Harlech boots combine the classic silhouette of an ankle boot with the design of cap-toe derby. What makes these more dressy than most of our other options is the cordovan leather—the high shine burnish and hand finish makes them read as formal.

These Beatle boots are another great option for any man who loves a good Chelsea boot. John Lobb’s Freddi boots are so simple yet so elegant. They feature a side zip and a higher wedge heel for a bit of rock-and-roll. This is the ultimate cool-guy shoe.