Dress Boots: What They Are & How to Wear Them

‘Dress boots’ might sound like a contradiction – kind of like ‘formal thongs’ – but just because your shoes cover the ankle doesn’t mean they can’t look fancy. Men’s dress boots actually come in all shapes and sizes, and you can wear them (more or less) anywhere that Derbys, Oxfords and Brogues are accepted. If your suit pants are hemmed low, most people won’t be able to tell the difference anyway.

So what qualifies as a men’s dress boot? And how do you style them? That’s what we’re tackling today.

The Bronson Brown Chelsea Boots

The better question might be, ‘What makes a dress boot dressy?’ There are no hard and fast rules with dress boots, but there are certain characteristics that make some boots ‘dressier’ than others. The toe, for starters. Casual boots usually have a wider, more rounded toe. Dress boots will be sleeker, sharper, sometimes with a squared-off chisel toe. They’re usually made from full-grain leather, rather than suede or nubuck, and the soles will be leather (or discreet rubber in a pinch) – never crepe or thick, chunky rubber. Broguing is also a sign that your boots might be better for weddings than weekends.  

The Osbourne 2.0 T.D.Moro Chelsea Boots

Short answer: yes! Don’t let anyone tell you otherwise. Chelsea boots with a suit, for example, is a classic modern look. The trick is picking the right boot. You usually want darker shades of leather – in high gloss, rather than matte – and they need a sharp, structured silhouette. Also, pay some attention to your suit pants. Boots and suits require a slim, tailored leg. Nothing too baggy or too tight. Go for a light break, or no break at all, and a narrow leg opening. The last thing you want is loose hems flapping around your shiny leather boots.

For men’s dress boots, stick to Chelsea boots, Brogue boots, Derby boots and Chukka boots (not all Chukka boots, though. More on this below…) Desert boots with crepe soles will always veer more casual than dressy. Same goes for heavy, bulbous Military boots. There are exceptions, of course, but if you stick with the broad characteristics listed above (sleek, sharp, glossy, full leather, slim heel) you’ll be fine.

With their clean lines and simple gussets, Chelsea boots should be your go-to dressy office boot. For navy suits, simply pair some brown LUCCA Chelseas with a matching leather belt, white shirt and tonal geo tie. Our OSBOURNE 2.0 Chelsea boots are also a good option here. If black boots are more your style, try some sharp JAGGER boots with a charcoal suit, or maybe the high-profile BRONSON. Remember to keep your suit pants hemmed slightly higher for this look – a slight break is as low as you want to go. If the fabric is bunching, you need to take your pants up.

It’ll depend on the wedding, but again, Chelsea boots will rarely steer you wrong. For extra style points, try some oxblood OSBOURNE 2.0 Chelseas with a navy or brown suit, light pink shirt and tonal tie. Don’t be afraid of Chukka boots here, either. Chukkas are generally considered a more casual men’s boot, but you can definitely dress them up a little. A pair of sharp-toed ADAMS Chukka boots with a three-piece charcoal suit is a great look for winter weddings. They’re also much more comfy on the dancefloor than your standard pair of Oxfords.

The Osbourne 2.0 Black Chelsea Boots

Cocktail parties are usually a step down from business and corporate, in terms of dress code. You’ll see a lot of ‘semi-formal’ and ‘smart casual’ on invitations, and that opens up a few different styles of boot. A pair of laid-back DEXTER Chelseas under some dark, slim-fit jeans and a knit blazer is a great cocktail outfit, or you could try some LENNON high-ankle Chelsea boots with tan dress chinos and a suit jacket. These guys are tobacco suede, which usually wouldn’t be considered dress boot material, but cocktail parties have a little more leeway.

For date nights, a plain Chelsea might be a little conservative, so try something with a bit more personality. A pair of black UTAH ankle boots under black slim-fit jeans and a collared shirt gives your outfit a dressy edge. Same goes for the MASSIMO military boot. We wouldn’t recommend this look for the office, or the summer wedding, but for date nights it can definitely work. The glossy leather INGRAM has a more slim-line profile than your standard combat boot. All it needs are some dark jeans, a button-up shirt, and a sharp woolen trench. Don’t forget a nice dress watch, to complete the outfit.

The trick with most dress boots is polish. They need to gleam. That’s what makes them dressy. If you need a few pointers when it comes to leather care, check out our polishing guide. Investing in some weatherproof spray, a good shoe brush and shoe polish will extend the life of your dress boots and keep them looking fancy for years. As with all things leather, you get out what you put in.