The Ultimate Men’s Dress Boot Guide

The men’s dress boot and it’s variants have come a long way since the early days of foot wear. Today we are faced with a plethora of different styles spanning different eras and generations. Boots that were once designed for a practical purpose are now worn for comfort and style. So how do we start our men’s dress boot guide?

We’ve rounded up some of the most popular and timeless styles ever worn on a man’s foot. We designed this guide so that even the most fashion illiterate of men can just pick a pair and up their style game instantly. Without further ado we give you four styles you just can’t go wrong with.

The Lace-up Boot

We have come a long way in shoe design. The modern lace-up boot has served countless countries in armed combat.  The contemporary iteration of the combat boot serves just as well in no man’s land as it does on a sticky bar floor at one in the morning. It’s the work horse of the modern man’s wardrobe, always have a pair at the ready cause they can go with any style from cowboy to urbanite.

Thursday Boot Company Captain Men’s Lace-up Boot

PROS:

• Complements a variety of outfits, from casual to formal.
• Handcrafted with genuine leather that improves with age.
• Cork-bed midsoles that mold to your feet and studded rubber outsoles for support and durability.

CONS:

• Requires careful consideration of sizing, typically ½ size smaller than sneakers.
• Handcrafted marks and colors may not appeal to those preferring uniformity.
• Premium materials and craftsmanship come with a higher cost.

The Captain Ankle Boot is a versatile, handcrafted leather boot designed to complement any outfit, from jeans to business suits. Made with high-quality materials and Thursday’s signature craftsmanship, it features a supple glove leather interior, studded rubber outsoles, and cork-bed midsoles for comfort and durability. With a timeless minimalist design that improves with age, these boots are built for both style and reliability. For the perfect fit, order your usual leather boot size or ½ size smaller than your sneaker size.

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Dr. Martens 1460 Originals Boot

PROS:

• Retains classic and iconic design elements for timeless style.
• Enhanced comfort with SoftWair sockliners and memory foam pods.
• Slip-resistant GRIP-TRAX soles provide improved safety and stability.

CONS:

• May not appeal to those seeking lightweight, minimalist designs due to its heritage aesthetic.
• Water-resistant leather requires maintenance to preserve its easy-clean properties.
• Upgrades like GRIP-TRAX and memory foam contribute to a higher price point compared to standard boots.

The Original 1460 design retains its iconic heritage with features like yellow welt stitching, 8-eye lacing, grooved air-cushioned soles, and a scripted heel loop. Upgraded for modern functionality, it now includes a re-engineered slip-resistant GRIP-TRAX sole, breathable SoftWair sockliners with memory foam for ergonomic comfort, and a lightweight, flexible anti-fatigue construction. Made with water-resistant, industrial leather, these boots are spill-resistant and easy to clean, combining timeless style with practical durability.

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The Chukka and The Desert Boot

The Chukka came into being through the game of Polo, where Chukka signifies a period of play. This ankle high boot comes with 2 to 3 sets of eyelets and always in a suede or calfskin leather upper. The desert boot is a derivative of the Chukka which came into being when it was worn by soldiers in the desert campaigns of World War 2. The desert boot has a crepe rubber sole and suede upper, they were popularised by Clarks shoes in the 1950s and they are still making them today.

Clarks Men’s Desert Chukka Boot

PROS:

• Iconic and timeless design that has remained fashionable across decades.
• Offers a sense of nostalgia and connection to history, appealing to those who value heritage.
• Simple yet versatile style, suitable for a variety of outfits and occasions

CONS:

• Modern versions may lack the original build quality of the 1950s design.
• Simplicity might not appeal to those looking for more contemporary or detailed aesthetics.
• May not include updated features or materials found in newer footwear designs.

This is the original desert boot made by Clarks. Most likely they are not built the same way today as they were in the fifties, it is still nice to feel like you can grab a piece of history and wear it on your feet all day. This timeless design has endured many decades of fashion trends that have come and gone and seeing such a simple yet effective design, it is no surprsie that it still remains highly regarded by the stylish gentleman.

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The Chelsea Boot

The Chelsea boot has been around since the 1840s but came into its own during London’s infamous swinging sixties. Once revolutionary bands like the Beatles and Rolling Stone front man Mick Jagger started wearing them, they took on a life of their own and haven’t slowed down since. The great thing about the Chelsea boot is it can be worn in any combination, dressed down with jeans or dressed up with Chinos and a blazer. Just beware of the sizing, as the tighter fit might mean you will have to look into half sizes.

Classic Chelsea Boots by Gifennse

PROS:

• Elegant design enhances style and professionalism for business occasions.
• High-quality cowhide leather and handmade coloring process offer durability and unique craftsmanship.
• Breathable lining and cushioned insoles provide superior comfort and moisture control.

CONS:

• Formal design may not suit casual or rugged wear preferences.

These Chelsea boots combine classic Italian craftsmanship with modern comfort and practicality. Designed with an elegant European silhouette, they exude sophistication, making them ideal for business settings. Crafted with high-quality cowhide leather and a handmade coloring process, the boots showcase artisanal attention to detail. A breathable pig leather lining and cushioned insoles ensure comfort, moisture absorption, and shock absorption, while the flexible structure allows effortless movement throughout the day.

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Blundstone Original Series Chelsea Boots

PROS:

• Amazing for everyday casual wear as well as business casual office days.
• A high level of water-resistance make these boots ideal for wet weather conditions while still looking modern.
• Enhanced comfort system with shock-absorbing midsoles and customizable footbeds ensures support during extended wear.
• Lightweight yet durable TPU outsole provides resilience for a variety of activities.

CONS:

• A more casual style that is not suited for more formal settings
• Require maintenance to maintain the appearance and water-resistant properties of the leather.

These boots combine premium water-resistant leather with modern design elements, featuring a sleek black aesthetic that is both versatile and stylish. Engineered for comfort, they include the SPS Max Comfort system, a cushioned midsole, and a removable footbed with XRD Technology for shock absorption and personalized support. With a lightweight yet durable TPU outsole and breathable leather lining, these boots are crafted for long-lasting wear and all-day comfort, making them ideal for both casual and adventurous settings.

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Hope That Helped You Out

And that about wraps it up for your men’s boots guide for 2024. If we missed anything you think we should have covered don’t hesitate to let us know via Facebook or our contact us page. If you enjoyed this one then check out our other recent articles like this one about the best dive watches for men and this one here about leather satchels for guys.