From Chelsea to Wallabee: A Guide to Men’s Boot Styles

Boots have a place in every well-curated men’s shoe collection. Ideally, you’ll want a couple of pairs to cover different settings. When it comes to popular male boot styles, the classic Chelsea and Chukka boots often come to mind.

However, your choices don’t end there. There is a broad array of male boot styles that extend beyond these two popular options. Each style is built on a different shape and fits into a different rotation.

Fashionable and practical, desert boots are a popular addition to a men’s shoe collection. These boots trace back to Northern Africa, where British soldiers relied on them during desert campaigns thanks to their comfort and durability.

Desert boots are often made from suede leather. The reason is mainly practicality. Traditional desert boots were designed for hot, dry conditions, and suede was lightweight and flexible compared with the heavier and rigid leather used in work shoes.

Combined with a lower, ankle-grazing fit and a soft crepe rubber sole, desert boots hit the sweet spot between rugged and refined. You can easily pair them with everything from casual jeans to tailored chinos from spring straight through to mid-fall.

When it comes to styling them, desert boots can look great in many different scenarios. For instance, for a more casual look, you can pair them with a plain T-shirt, a button-down or checked flannel shirt or a sweater and jeans.

Desert boots can complement your look for smart casual occasions, too. Paired with slim chinos and a more elegant button-up shirt, these boots can be perfect for this type of event.

Created by J. Sparkes-Hall, a bootmaker for Queen Victoria during the Victorian era, Chelsea boots were originally designed as an elastic-sided style to replace the inconvenient lace-up riding boots of the time. Their sleek design and easy pull-on style have remained popular ever since.

Smart yet cool, with a hint of edge, Chelsea boots have been worn by many famous faces over the years. It’s safe to say they’re a must-have style in a well-curated men’s shoe collection.

Chelsea boots are versatile and can be styled with a number of different clothing pieces. You can wear them for work, and they look as good after hours and at the weekend. They can be worn with a suit, jacket, chinos or jeans.

Originally introduced by Clarks in the 1960s, this distinctive style is known for its moccasin-inspired shape, chunky crepe sole and simple lace-up design.

Unlike the sleek silhouette of Chelsea boots, Wallabees have a more relaxed and rounded shape. Their low ankle height and soft suede or leather upper give them a casual feel, while the chunky sole adds a little extra character. They’re not quite as polished as a Chelsea boot, but that’s part of their charm.

Wallabees are also easy to style with casual outfits. You can pair them with straight-leg jeans and a simple tee for an everyday look, or swap the tee for an overshirt or lightweight jacket when the weather cools down. They also work well with chinos if you want something slightly smarter without losing their laid-back feel.

Because of their distinctive shape, Wallabees tend to become a statement piece in an outfit. You don’t need to overthink the rest of your look. Keep your clothing simple and let the shoes do the talking.

Lace-up boots are another footwear style worth having in your men’s boot collection. Unlike Chelsea boots that have elastic side panels, lace-up boots use traditional laces to secure the foot. This gives them a more structured look and lets you adjust the fit.

There are plenty of variations to choose from, ranging from rugged work-inspired boots to sleek leather styles that can be dressed up. For a casual outfit, try a pair of leather or suede lace-up boots with jeans and a T-shirt, adding a jacket or overshirt when needed.

Chinos are another easy match, particularly with a cleaner pair of boots. If you’re dressing for a smarter occasion, opt for a sleek leather pair with tailored trousers. Just keep the overall outfit relatively polished so the boots don’t look too heavy.

The right pair can take you from everyday errands to a casual dinner, making lace-up boots a practical addition to your rotation.

Dress boots aren’t a style of their own, but a category based on how polished a boot looks. Sleek leather Chelsea boots with a slim sole are a common example. Some streamlined leather lace-up boots can also fall into this category.

What defines most dress boots is their sleek, streamlined shape, a relatively slim sole and minimal detailing. This gives them a more polished appearance than chunkier and rugged styles.

Unlike the casual Wallabees and Desert styles mentioned above, these boots can complement smarter outfits. They can easily be paired with tailored trousers for a polished look or worn with chinos when you want something a little more relaxed.

However,  you don’t need to save them solely for special occasions. Pair polished leather dress boots with dark straight-leg jeans, a crisp button-up shirt and a structured jacket for a smart-casual dinner.