If you want to make your fits extra smart, yes, you can invest in a solid pair of brogues or Oxfords, but you should also check out some of the best dress boots for men out there. First introduced during the Victorian era, this silhouette was worn by VIPs and royalty during very special events. And while absolutely any guy can get a pair now, that doesn’t take away the fact that they just look awesome.
The problem is, with so many different designs and styles to pick from, searching for the perfect dress boots for men can be a bit of a challenge. There are military-inspired ones, pairs that lean more towards a rugged hiking aesthetic, and versions that feature a Chelsea-esque vibe. If you’re not entirely sure where to begin, then you’ve come to the right place.
In this comprehensive guide by OPUMO, we’ve rounded up some of our favourite dress boots for men right now. From independent brands like Oliver Cabell to fashion houses such as Paul Smith, there’s bound to be one here that complements your personal taste and, of course, your budget. So let’s check them out!
The best dress boots for men
Aurélien City Chelsea Boots
To kick things off, we have to talk about the City Chelsea Boots from Aurélien. Handcrafted using supple grain leather, you’ll find a pair of chunky pull tabs around the heels for extra convenience. While most Chelsea boots rest on top of black soles, this one switches it out for a creamy one instead for that true Mediterranean vibe. And while it’s available in a total of eight colour options, the brown one is probably the best of the bunch.
Myrqvist Tjärnö Jumper Boot
Inspired by combat boots that were designed for paratroopers back in the day, Myrqvist’s Tjärnö Jumper Boot boasts a Goodyear welted construction that’s been specifically engineered to last years and years (and years). The upper is made with premium full-grain calf, and to make things even more rugged, it’s finished with 360° storm welt for water protection, and a series of chunky metal D-ring eyelets that run across the top of the shoe.
Velasca Lampionèe Chelsea Boots
While Velasca is probably known more for its Oxfords and Derby shoes, that doesn’t mean you should overlook its dress boots for men. Just take a look at the Lampionèe Chelsea Boots, for example. Released as part of the Milanese imprint’s Autumn/Winter 2024 collection, it’s crafted from smooth calf leather and decorated with traditional brogue detailing across the front. As if that wasn’t cool enough already, the midsole is also infused with Vibram, which is one of the most comfortable rubbers that you can get on any shoe.
Oliver Cabell Chelsea Boot
Oliver Cabell has been dropping some of the cleanest sneakers around, but with its Chelsea Boot, it’s stone cold proof that its other models are just as good (if not better). For this version, the top half is crafted from three ounce soft split suede, and all of this rests on top of an Italian crepe sole that’s made from 100% pure virgin Hevea milk. The shoe is then hand stitched and lasted in Albacete, and packed with a limited edition dust bag which is always nice to have.
KLEMAN Tonnant VGT Chelsea Boots
We just can’t talk about the greatest dress boots for men without giving the Tonnant VGT Chelsea Boots from KLEMAN a special shoutout. Made from grain vegetable leather in an Italian tannery, this sustainable technique gives it a special patina that’s unique to each and every shoe. Underfoot, the chunky sole measures up at an impressive 2.5 centimetres, and it’s finished off with a duo of branded pull tabs around the back.
Tod’s Chelsea Boots
If you’re on the lookout for dress boots for men that’ll stand the test of time, Tod’s Chelsea Boots should probably be one of the first pairs that you check out. Crafted from black calfskin leather that has been perfectly polished, these are fitted with a wider-than-usual opening and elasticated sides for extra convenience. If you’re not entirely sure about the fit, the brand suggests that you should go for your usual size and you should be good to go.
Brunello Cucinelli Ankle Boots
Yes, Brunello Cucinelli’s Ankle Boots aren’t cheap, but believe us when we say that they’re worth every single penny. Since the dawn of time itself, the Italian label has been prioritising exceptional craftsmanship and premium materials above all else, and it really shows with this silhouette. Every single leather panel and every single cut and stitch is executed immaculately, and there’s even a zip across the side that runs as smooth as butter.
R.W. Williams Comfort Craftsman Boot
Handmade from a single piece of yearling leather in R.W. Williams’ Adelaide workshop, the Comfort Craftsman Boot is a seriously versatile shoe that can be used for light work, daily dressing, or more formal wear. What we love most about this particular pair is the square chiselled toe and the sharp heel that gives it an extremely masculine appearance. It’s also available in three colour options, but the chestnut just can’t be beaten.
Paul Smith Falk Boots
And last but not least, we have to talk about the Paul Smith Falk Boots. Simple, sleek, and seriously sophisticated, it’s everything that every guy wants in a pair of dress boots for men. The leather just feels so good that you honestly need to try these in-person to be able to fully appreciate it, and they’re finished off with a pair of 100% rubber soles that make things a lot more lightweight and a lot grippier. What’s there not to love?
For more like this, check out the best Chelsea boots for men.
