How to Pick the Right Type of Dress Boot

Let’s get something out of the way: boots can be dressy. Don’t let anyone tell you otherwise. While we’re more used to seeing round-toed Chelseas' under a pair of jeans, or chukka boots with some chinos, there’s a whole other category out there known as ‘Dress Boots’. And this needs some unpacking.

Dress boots aren’t one specific type of boot. It’s an umbrella term that usually comes with certain characteristics attached: polished leather (but not always), sleek lines, sharp chiselled toes, leather soles, a pronounced heel, and maybe some broguing. The word “boot” has mostly come to mean “casual boot”, but dress boots are the exception. They provide all the sturdiness of your classic leather boot, plus the sophistication of Oxfords or Derbys. And yes, you can (and should) wear them with a suit.

In this article we’re going to run through the history of men’s dress boots, and how to pick the style that’s right for you.

The Lennon Oyster Chelsea Boots

There are dozens of boots out there that technically qualify as ‘dress boots’. These include Chelsea boots, brogue boots, and even ankle-height desert boots. What makes a dress boot ‘dressy’ is mostly down to form, rather than function. Boots were traditionally made to be sturdy, hard-wearing and weatherproof. Dress boots, on the other hand, are there purely for style. They’re made for the man about town, not the man on horseback.

If you’re unsure whether a boot qualifies as dressy, check for these signs. Is it sleek, rather than chunky? Does it have any broguing on the leather? Is it simple, i.e. no contrast stitching, metal eyelets or flashy welts? Does it have a leather or discreet rubber sole? Is there a pronounced heel? All these things suggest a dressier boot.

A quick note on suede: suede boots are mostly casual boots, but a heeled, high-profile, sharp-toed Chelsea boot is the exception. Something like the suede OSBOURNE 2.0. These won’t get you all the way to black tie, but they’ll do fine for cocktail parties and semi-formal events.

The Bronson Brown Chelsea Boots

Dress boots have their origins in riding boots, which can be traced back to the 17th century. By the Victorian Period, they’d evolved into something approaching a modern dress boot – a symbol of status, wealth and style. These were mostly made from patent calfskin leather, and were obviously out of reach for the average peasant in the street looking for a pair of shoes. Dress boots in those days tended to be very high-profile, often reaching halfway up your calf. As time went on, the profile shrank, the complex laces disappeared, and Chelsea boots and Desert boots became the norm.

Today, dress boots are worn more or less wherever you’d wear dress shoes. The two can be seen as interchangeable.

Chelsea boots are the classic modern dress boot. If you’ve only got room on your shoe rack for a single pair of dress boots, make them Chelseas. The BRONSON or the OSBOURNE 2.0 are great places to start, but really you should be looking out for anything sleek and slim, with a sharp, chiselled toe. Stay away from round-toed Chelsea boots with a low ankle profile. These are strictly for casual wear. When it comes to styling, try some LENNON black Chelsea boots with a charcoal suit, black belt and white dress shirt.

Dressy chukka boots? Yep, it’s a thing. You just need to be smart with your styling. For starters, pick a premium leather Chukka with a sharp toe and simple lace design, like the ADAMS. Under a navy suit, these are perfect for everyday office wear, or you can try them with dress chinos, button-up shirt and a knit blazer. That’s a great look for weddings and semi-formal events. Always make sure to pair your Chukkas with plain cotton dress socks. Nothing wooly or too loud.

We’ve written a whole guide to broguing, if you’d like to learn more about that technique, but as a general rule: brogue boots are dressy boots. There are some exceptions, like our SAMUEL military boots. Wing tip brogues in particular are perfect for formal events, or even black tie. If you’re pairing them with a tuxedo, just make sure they’re made from black patent leather.

In terms of fanciness, Desert boots probably sit slightly below Chelseas and Chukkas. We’ve written about them before. As a dress boot, the same rules apply: you want a sleek silhouette, a pointed toe, and (ideally) a strong heel. Something like the BRODY Desert boot is perfect. We wouldn’t recommend wearing this with black tie, but a laid-back khaki suit, or chinos and a knit blazer, works just fine. For a slightly different style, try our UTAH ankle boots. They look great with dark indigo jeans and a button-up shirt.

If you’d like to explore more dress shoes, or get some advanced styling tips, check out our dress shoes beginner’s guide.