11 Great Pairs of Boots for When You Want to Dress Up

• Affordable price
• Beckett Simonon has good materials for what you're paying
• Simple, high-shine leather that has a formal air

• Oxford boot reads as an old-fashioned style

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 if you're shopping on a budget, I think Beckett Simonon is a great value.

• Thursday is good value
• More of a laid-back style

• Not exactly "dress" or "formal" in the true sense

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.

• Beautiful leather boots
• One-piece upper makes for a really good look
• Incredibly comfortable

• Elastic and pull tabs should be somewhat hidden in a formal context

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 where 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.

• Absolutely beautiful, a stunning boot
• Higher heel—1.75 inches to be exact—feels a touch more formal
• Crackled leather makes them more versatile for a dress down

• The price, obviously

If you want to know the boots I'm really lusting after, it's these. Husbands Paris is one of my favorite suit brands. I'm just really all in on the Serge Gainsbourg thing, and the boots (which now come in a brown as well) are part of that look. These are made from a gorgeous black patent leather that shines well for a formal occasion but has a crackled texture that can be dressed down as well.

Same thing here, a full smooth upper just looks a bit more slick. Normally, the way to not do an elastic ankle is a a zipper, but a Jodhpur boot uses a buckle to open the shoe up. I like it. It's an old-school touch that, again, makes a shoe read as more formal.

• A classic of the Thom Browne lineup
• Actually quite versatile, a nice mix of dress and combat touches
• Great materials

• A bit too Fashion for some tastes

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.

• A classic Americana look, from the top cowboy boot brand
• High-end and high-shine options for dress occasions
• Can work with anything because it's such a strong look

• A lot of guys are intimidated by cowboy boots
• Requires a wider, longer pant
• Great materials means high price point

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 shine. Lastly, you can lean into the western thing and go exotic. I prefer American alligator, but ostrich is a classic western choice.

• Great value
• In a simple black, boots can be dressed up pretty easily

• Not as nice a pair of boots as you can get
• Tougher to find options that pass the black tie test

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.) 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.

• Benchmade in the traditional shoe making capitol of the world
• Supremely comfortable

• The RRL price tag

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.

• Available in Standard and Wide fits
• Cork midsoles form to your foot shape

• Runs a half size large

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.

There are a few key factors to keep in mind when it comes to selecting the perfect dress boot for your wardrobe. First, think about your existing wardrobe and lifestyle and how you’ll wear your dress boots. If you have a lot of cowboy-cut jeans in your closet, you might find the Tecovas more suitable than, say, the Beckett Simonon shoes. If you wear a suit to work every day, something simple and classic like a Chelsea boot will be a great pick.

Another factor to consider is the design features of the shoe, because these are usually good indicators of comfort. If you know you have wide feet, a square toe will serve you better than an almond one. If you need extra arch support and cushioning, pick out a pair designed with those qualities.

We’re not going to say something is great unless it’s actually great. Every product in Esquire’s roundups is carefully chosen by our fashion and e-commerce teams.

We’ve compiled the dress boots we’ve tried, tested, and loved over the years, as well as the dress boots that the rest of our stylish colleagues here at Esquire endorse. We’ve put in the research, we’ve worn these ourselves, and now we’re recommending them to you because they’re just that good.

No two tastes are the same, and no two men are the same. Your proverbial mileage may vary. But if you’re looking for the right place to start, with advice from folks who care (possibly too much!) about this sort of stuff, this is the place to be.