Men's dress boots are more formal than casual boots and, as such, there is less of a need to focus on warmth and weatherproofing. As long as they look good, men can feel free to be a little more adventurous in their choice of style and material. To help you choose the right pair of boots, we've compiled a list of some of our favorite dress boots.

Quick Picks

Blundstone BL585 Classic 550 Chelsea Boot

The Blundstone BL585 Chelsea Boot is a classic dress boot with premium rustic brown leather. They are water-resistant, elastic side boots that feature additional cushioning for comfort. You can purchase them on the Blundstone website in your standard US shoe size.

Blundstone BL585 Classic 550 Chelsea Boot

A a classic dress boot 

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Clarks Clarkdale Hall

This traditional chelsea boot from Clarks is a great option for men who want a high-quality dress shoe. It features a premium cognac suede upper, a comfortable padded topline, and an ankle loop for quick and easy on/off. The heel and layered sole are finished with crafted detail, while the Cushion Plus footbed delivers targeted all-day comfort.

Clarks Clarksdale Hall

Targeted all-day comfort

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Johnston & Murphy Copeland Chelsea

Johnston & Murphy Copeland Chelsea is  an effective mix between classic and modern. The boots are crafted of water-resistant oiled full-grain leather, as well as sheepskin leather/moisture-wicking textile lining, side elastic gores for on/off ease, memory foam cushioned footbed with sheepskin/performance mesh covering, and super-flexible genuine crepe rubber sole.

Johnston & Murphy Cop

An effective mix between classic and modern

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Clarks Desert Boot 2.0

The Clarks Desert Book 2.0  is an iconic, re-engineered version of the original 1950 shoe with a slightly wider last to fit modern feet better. It also has improved cushioning for all-day comfort and technical elements like grip and durability.

Clarks Desert Boot 2.0

The re-engineered version of an icon

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Red Wing Heritage Weekend Chukka

The Weekender Chukka is a casual design that looks good in the office, on the weekend, anywhere. Its lightweight and flexible construction ensures it will be comfortable enough for all-day wear, even without socks. The Hill outsole provides traction and sleek styling. The boot has a durable Moc Toe with waxed Black Harness leather, Goodyear welt construction, and comes in Red Wing's Classic Line.

Red Wing Weekender Chukka

Looks good in the office or on the weekend

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Thomas & Vine Legend Wing Tip Ankle Boot

The Thomas & Vine Legend  Wing Tip boot is an all-purpose ankle boot. It comes with a pebbled accent and a wingtip detail, which speaks for itself. It's made of genuine leather uppers, has inside zipper access, contrasting pebbled accents, a cushioned footbed, one inch heel height, round toe construction with added wingtip details.

Thomas & Vine Legend

The pebbled accents speak for themself

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Men's Dress Boots Buyer's Guide

If you're looking for a comprehensive look at dress boots be sure to read our guide to men's dress boots.

What are dress boots?

Dress boots are men's footwear that fall into the business casual or dress shoe category, which is to say they are designed for more formal occasions than your average workday. However, they do not need to be boring and conservative like traditional dress shoes. There is an increasing availability of options in modern styles with unique leathers and treatments.

Types of Dress Boots

  • Chelsea boots are boot-style shoes that became popular in the 19th century as an alternative to riding boots. Now, they are worn by both men and women as everyday casual footwear, but are also considered appropriate for formal occasions.
  • Chukka boots are ankle-length boots that resemble desert boots, but are intended for dressier attire.
  • Dress boots are another option for high ankle boots. Dress boots have multiple eyelets and open lacing, similar to Chukka boots. Some have a pull loop and metal hooks to lend a more casual feel to this refined style. They are typically made from beautiful leather, have fine laces, and a thin rubber sole.

What to Look For

Here are some factors to consider when you're shopping around for men's dress boots.

Material The most common materials used in dress boots are leather and suede. Leather is more formal, but it can attract dirt and stains if not properly conditioned. Suede's texture and appearance make it a little dressier than normal leather, but it also makes it harder to clean (it can even stain if you're not careful).

Toe-style Dress boots typically come in round and pointy toes, but there is no one that offers both styles. This is just a matter of preference. Round-toe boots tend to be more conservative, whereas pointy-toe boots are bolder and trendier.

Lacing System
Laces are more formal than straps or zippers, but they can be difficult to operate. Strap closures are easier to use, but aren't quite as stylish. Metal rings offer an ideal balance between the two.

Dress boot sole types  typically come with a thin rubber or leather sole. Leather soles are more formal, but they can wear out after extended use. Rubber soles have a more modern appearance and tend to be more durable.


In conclusion,  dress boots are a great alternative to casual or dress shoes. The sturdy leather uppers and rubber soles make them appropriate for any formal occasion, while the sleek styles and unique finishes mean they can be worn with more casual clothes as well.