As the weather transitions to the cold and damp climates of fall and winter, a quality dress boot becomes a must-have in your wardrobe. While similarly versatile to oxfords or derbies, dress boots offer added protection for the colder months. Our men’s heritage boots come in a variety of styles ranging from formal to casual. Learning to match different boot styles to the occasion is a key part of maintaining a stylish look for every event.


Stylish gentlemen are no longer limited to only wearing shoes for formal occasions. A quality leather boot can be both a functional and refined alternative. However, care must be taken to match your chosen style with the formality of the occasion. 

  • Black Carleton’s

A Chelsea boot is an excellent option for formal occasions thanks to its sleek, sophisticated look. A black leather boot, such as the Carleton Boot in black, is a perfect match for such occasions as it pairs well with a tailored suit. 

  • Black Bedford’s

Another fine option for formal dress would be a lace-up wingtip or brogue boot. The Bedford Boot in black is an excellent choice as it complements a suit very nicely. However, much like wingtip oxfords, the brogue design brings a slightly casual element to the boots and may not be appropriate for the most formal occasions. 

A good rule of thumb is to choose darker colours and smooth and sleek designs for your more formal boots. It’s also important to remember that when wearing boots, the cut of your trousers is key. A slimmer leg ending just at the top of the boot works best for a sophisticated formal look.

Smart Casual

Boots are similarly well suited for a smart casual style. Their versatility allows them to provide an element of sophistication to any casual outfit.

  • Bedford Boot in Brown

Wingtip brogue leather boots are a perfect choice for smart-casual outfits. Their smooth design provides a smart look, while the brogueing on the toe makes them slightly more casual than a cap-toed alternative. In a lighter colour such as the brown Bedford Boot, they make an excellent addition to any smart-casual look. For a more interesting alternative, go for the Bedford Boot in Country Calf, to add some texture to your outfit. Paired with dark wash denim and a sharp oxford shirt and blazer, wingtips provide a classic, smart look.

  • Carleton in Brown

Chelsea boots are another timeless option for any smart-casual dresser. Lighter colours and different textures are good choices for less formal wear. The Carlton Boot in brown is a smart, sophisticated option that would make a great addition to any wardrobe. Due to their sleek design, Chelsea boots pair well with smart trousers such as chinos or wool pants. Add a fine knit roll-neck and a wool coat for a complete, smart look. 


During the fall and winter seasons, a rugged pair of Canadian boots is a must-have for any gentleman’s casual wardrobe, providing protection from inclement weather while maintaining a polished look. 

  • Ammo Boots

The Ammo Boot in both black and oxblood are excellent casual boot options. Paired with denim and a flannel shirt or chunky sweater, the Ammo Boot completes a rugged and relaxed look, perfect for the fall and winter months. 

  • Brewer’s Boots

An excellent alternative choice would be the Brewers Boot in copper. It’s unique leather upper changes with every movement, resulting in a rugged look well suited to casual fall or winter outfits. Pair with light-washed denim or chinos and a bomber jacket for a strong look.

  • Fred Boots

For a stylish, comfortable alternative the Fred Boot makes an excellent addition to your casual wardrobe. When worn with jeans or chinos, the Fred Boot offers a harsher weather alternative to a sneaker for a smooth casual look. 

Boot Care

As with any quality shoe, boots should be taken care of to make them last and maintain their appearance. Nourishing the leather is a must for a long-lasting boot and there is no better product for this than Saphir Renovateur. Pair it with a colour-matched Saphir Shoe Cream to maintain the colour and further nourish the leather. Saphir Pate de Luxe Shoe Polish is an excellent product as well, to both protect your boots and achieve a high gloss finish, perfect for the most formal looks. Finally, a pair of cedar shoe trees is a smart investment to maintain the shape and wick away any moisture inside your boots. Taking the time to care for your boots is essential to maintaining a sophisticated style.

Before investing in a premium pair of boots, think about which occasions you’ll most commonly find yourself in, and choose a design that best suits your lifestyle. If you are unsure, a sleek design such as a Chelsea or Wingtip Lace-up in a dark colour is a good choice as it suits both formal and casual looks. With a quality pair of leather boots, you can confidently take on any occasion while protecting your feet from the harshest weather fall and winter have to offer!

Andrew Bedford