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The Best Boots for Dressing Up: Every Occasion, Every Budget

From polished leather cowboy boots to your classic cap-toe, our guide to the best dress boots for men covers which to buy, how to wear and how to care of them.

collage of three pairs of boots in black and brown Courtesy

By Evan Malachosky

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Whether you wear them year-round or are attending a winter wedding, there are a number of reasons (and ways) to wear boots with a suit. Collectively called “dress boots,” despite there being no real definition, the below boots offer a refined take on classic silhouettes: Chelsea, Cowboy, Chukka, and beyond. They’re a step above your basic Timberlands, that’s for sure.

Products in the Guide

  • R.M. Williams Comfort Craftsman boot

    Best Chelsea Dress Boots

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  • Johnston & Murphy Meade Cap Toe Boot

    Best Brown Dress Boots

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  • Allen Edmonds Dalton Wingtip Boot

    Best Black Dress Boots

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  • Tod’s Suede Chukka Boots

    Best Chukka Dress Boots

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  • Thursday Wingtip Boots

    Best Wingtip Dress Boots

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  • Beckett Simonon Easton Side-Zip Boots

    Best Side-Zip Dress Boots

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What Are Dress Boots?

A dress boot is, well, what you make it. While all-leather cap-toe boots — the taller cousin of cap-toe Oxfords — are a clear favorite for formal affairs, dress codes are more relaxed now than ever, and as long as you don’t wear your duck, muck or work boots to that upcoming wedding, you should be fine. Instead, opt for a finer boot with a less pronounced outsole, a leather (or sometimes suede) upper in a rich, dark color.

There are exceptions to these admittedly loose rules, but leather almost always looks best — and most elegant. If you add a rubber sole, for example, you trade some of that elegance for enhanced durability (and comfort, of course). That being said, if these boots are being saved for the occasional wedding, super-formal work stuff or other non-negotiable events, you don’t necessarily need to sell yourself short and get a hybridized boot. Go all leather, and embrace for an influx of compliments at your next cocktail hour.

Can You Wear Boots with a Suit?

Yes. Look no further than menswear expert Sid Mashburn‘s bottom half: the designer often wears Chelsea boots with his suits, a look, that with the proper trousers, creates a streamlined silhouette from head to toe.

Just ask bespoke suitmaker Jake Meuser. A few years ago, we asked him about the boots he had on, a pair of plain black Chelsea boots: “I’ve had these black Chelsea boots for years now,” he said. “My style has always been a mix of classic and more relaxed. I tend to wear jeans with a nice jacket so a pair of good Chelsea boots is perfect. Alternatively, they also work when I wear with a suit and tie.”

David Coggins (author, writer, fly fisherman) agrees. “You can definitely wear boots with a suit, if you’ve got a strong personality and you get the proportions right,” he says. “Chelsea boots can look great, but they’re narrow so they look better with a narrower trouser.”

If you’re not up for it, he says that the “suede loafers from Alden are a great winter option.” They might not be as buttoned-up, but they work, he explains. “They are a less dressy option, but look terrific with flannel or corduroy. They give the appearance that you just came from your country estate, whether you have a county estate or not.”

How to Style Dress Boots

“When it comes to [footwear], stick to black, dark brown or other warm brown tones, like heritage-inspired tan leather for vintage appeal,” an expert at the UK’s Suit Direct says. When on, they shouldn’t offer too much contrast — meaning they shouldn’t stick out. But that also doesn’t mean you should bury your boots with wide-leg (or ill-fitting) trousers. “[Your pants] should just graze the top of your shoes, or even leave a small gap. Trousers that are too long will bunch up and spill over your shoe – so make sure you know your leg measurements.”

Wearing a shorter pant leg offers opportunity to show off your boots, but if you’re feeling shy, a standard-length pant will offer quite the surprise when your pant leg rises, especially if you’re wearing cowboy boots.

How to Care for Dress Boots

Polished Leather

  1. Grab some gloves: Some polishes, creams and cleaners that treat leather able to stain your skin, and some have even harsher chemicals, which you definitely wouldn’t want to come into contact with bare skin.
  2. Clean your shoes: You never want to polish a dirty shoe; that’ll just damage the leather further and you’ll end up with an uneven polish. Brushing in quick, back-and-forth motions, clean across the entire surface of the shoe.
  3. Add the protective polish: Whether you use or cream, a little goes a long way. Apply it in circular motions, being careful not to overdo it.
  4. Brush and buff: Using the brush in a similar way to when you first cleaned off your shoes, brush off any extra cream.
  5. Heat it up and shine away: Take a cotton rag, one end in each hand, and quickly pull it back and forth, dragging it over the leather. This buffing process uses friction to create heat, which better bonds the polish to the leather, creating a finer shine.

Want further instructions? Refer to our guide to cleaning and polishing leather boots.

Suede

  1. Uppers stay dry: Your suede boots should remain dry throughout the entire cleaning process.
  2. Clean your soles: Apply a bit of cleaning solution to the sole. Scrub the soles using a magic eraser, toothbrush or paper towel depending on the extent of the stain or scuff. Immediately wipe the soap off and dry the sole, all while being sure not to swipe excess soap onto the suede material.
  3. Brush the suede: Next, gently brush any stained or scuffed suede with your suede brush. Doing so will remove most surface-level issues.
  4. Erase deep stains: For deeper dings, use a crepe block eraser. Rub in a linear motion until the stain fades.
  5. Fix the texture: Use an eraser (like a Nubuck Nap Restorer) to revive the suede’s natural texture.

Not making sense? Follow our guide to cleaning fussy suede shoes.

Available in narrow, regular and wide widths, R.M. Williams’s well-known leather Chelsea, the Comfort Craftsman Boot, is the ideal boot for next formal outing, whether it’s a (billion-dollar) business deal, cabin wedding or craft beer conference. Each one is made from a single piece of yearling leather featuring a comfortable (but subtle) rubber sole and a square chisel toe.

Equipped with the famous cap toe, Johnston & Murphy’s Meade Boot looks like a basic Oxford Derby with the proper pants on, but they offer much more ankle support than the low-top shoes. Wear these just like you would your favorite dress shoes.

For a little extra flair, try Allen Edmonds’s Dalton Wingtip Boot, a semi-tall style detailed with perforated wingtip trim and a contrasting liner. Available in four colors, you can wear these for as long as the sole lasts, which should be a long time if you’re only wearing it when you dress up (not all of us wear suits to the office). Then, when the uppers are really broken in, you can replace the sole and wear these patinaed wingtips wherever you want.

Imagine this: wearing plain suede boots with… a tuxedo. Truly, I’m thinking about it, because Tod’s Suede Chukka Boots are just the right amount formal to pair well with sleek black dress pants and a shawl collar jacket. If that’s pushing it for you, these rubber-soled boots would work well with brown, black, gray or green trousers, too.

Thursday’s best dress boots are wingtips, but cheaper. A palatable $235, these come in smooth black leather with shock-absorbing insoles and studded rubber outsoles. They’re taller and tonal, which makes them easier to match with a plain black belt.

Free from laces, meaning they’re pretty much smooth all over, Beckett Simonon’s Easton Boots slip on and off using a side zipper, a staple on ankle boots, but rarely seen on dress styles. The zipper is, however, super subtle. It’s tonal and tiny, meaning you can barely see it when your pant cuff hangs over it.

The Chelsea Boot is “an incredibly versatile pair of shoes that are worth the investment,” Sid Mashburn says. Sure, he’s selling his own product, but these are a style he truly wears. “They give you a very elegant line when worn with dress pants, and when worn with jeans you get a little bit of rock ‘n’ roll spirit. In the cooler months you could honestly wear a pair every day.”

The rubber outsole might break my own rule, but these are plenty okay paired with a linen or corduroy suit — something fall-ish.

Ideal when paired with a textured suit — i.e. wool, linen, jersey, corduroy or cotton canvas — these mocassin-style chukka boots are totally casual but they carry a refined edge, which helps them work, with the right suit, of course. The premium suede upper pairs well the crepe sole, and they’re unlined.

Complete with a cap toe, 5 blind eyelets, 4 antique hooks, an antique midsole and a rich, chocolate brown midsole, Viberg’s super-formal Halkett Boot is based on a 1940s-era Canadian Officer pattern, which the Canada-based brand sourced from its archive. These can be laced super tight, too, adding to the buttoned-up aesthetic.

Want to really make a statement? Wear Yuketen’s tall, patent leather cowboy boots. They’re hand-cut and hand-lasted from calf leather in Mexico and embroidered all the way up the shaft. A natural leather outsole offers contrast, while 1.5 inch heel lends, well, height.

If your suit skews workwear — i.e. it’s double-breasted and made from tough, peacoat-level wool — try John Lofgren’s Combat Boots, which have a more bulbous toe, tougher eyelets, silver speed hooks and contrast stitching. It’s truly battlefield-meets-boardroom in its design.

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