How to wear men’s boots

The Prestige Country Boot from Samuel Windsor is a versatile addition to any wardrobe

The Prestige Country Boot from Samuel Windsor is a versatile addition to any wardrobe
Image: Bespoke Unit

In times gone by, boots were commonly regarded as utilitarian footwear. Step forward to the present day and they’ve become a valued part of the discerning gentleman’s wardrobe. But it can still be somewhat confusing as to how they should be worn.

Here, Charles-Philippe of Bespoke Unit shares his pick of the best boots to wear for different occasions, along with expert tips on how to wear them.

How to choose men’s winter boots

For cold, wet winters, Goodyear welted rubber soles are a comfortable choice. The Prestige Country Boot from Samuel Windsor

For cold, wet winters, Goodyear welted rubber soles are a comfortable choice
Image: The Prestige Country Boot in black from Samuel Windsor

Thanks to their ankle support, boots are a popular footwear choice for men during the winter. Since many boot styles share the same construction techniques as dress shoes, they’re often worn as an alternative during the colder months.

Indeed, men’s leather boots provide the opportunity to remain stylish while protecting you from harsh weather. Unlike dress shoes, you can also wear them with thicker socks without being noticed.

However, not all boots are specifically made for winter. Therefore, it’s important to purchase the ones most suited to your needs. Firstly, you need to think about construction. Winter in most parts of the world can be particularly wet with heavy rainfall or snow. Therefore, cheap boots with cemented soles will fare poorly as they’ll leak and potentially fall apart.

The most affordable, and therefore common, method for making boots is Blake stitch construction. However, it’s best reserved for drier seasons as the visible stitching in the sole tends to slowly let in water.

The best construction method for winter boots is the Goodyear welt. Because the welt essentially consists of multiple layers that are independently stitched, it’s much more water resistant and can be resoled as many times as required, almost indefinitely. Since it’s a labor-intensive construction process, Goodyear welting can be somewhat pricey. The good news is that it’s possible to find quality, leather Goodyear welted boots online for less than $100.

How formal are boots?

These sleek, leather boots polished to a high shine work well with a formal suit

These sleek, leather boots polished to a high shine work well with a formal suit
Image: Bespoke Unit

Fortunately, boots are easy to wear and offer a unique touch of style to your attire. That said, it’s important to learn a bit about dress codes and footwear formality to easily integrate them into your wardrobe.

As a rule of thumb, the darkest colored boots and shoes are the most formal. For instance, black is the most formal while light tans and other less common colors are the most casual.

Similarly, the sleekness of your footwear plays a fundamental role. Thick soles and ornamentation render a boot more casual, while streamlined designs like Chelsea boots are quite formal. A good example of this would be brogue-style boots. While the profile of these boots is quite smart, the ornamentation reduces their level of formality.

Finally, the quality and choice of materials greatly affects the formality of a boot. As you’d probably expect, premium leathers are particularly dressy and become even more formal in dark colors and high-shine finishes. Textured materials like suede make your boot more casual. Some boots play with a combination of materials, such as these dress boots made with leather and tweed. While very stylish, the use of a second material makes them more casual and even lends them a sense of fun.

Best boots to wear with a suit

The black polished Chelsea boot is ideal for wearing with a suit. Prestige Chelsea Boot with Goodyear welted sole from Samuel Windsor

The black polished Chelsea boot is ideal for wearing with a suit
Image: Prestige Chelsea Boot with Goodyear welted sole from Samuel Windsor

Even the smartest boots are less formal than a dress shoe, so they can be difficult to wear successfully in conservative office spaces. The safest approach is to opt for the sleekest and most streamlined boot style – inconspicuous is your goal.

The best boot to wear with a suit is the classic Chelsea boot. A throwback to 1960s Beatlemania, Chelsea boots have since become an approved item of men’s business wear. Black leather Chelsea boots are by far the most conservative choice.

Looking for something a bit different? Another good option is the somewhat unorthodox yet formal monk strap boot.

Best boots for business casual wear

The Derby boot, also known as the Blucher, is an enduringly popular style. Prestige Boot in brown leather from Samuel Windsor

The Derby boot, also known as the Blucher, is an enduringly popular style
Image: Prestige Boot in brown leather from Samuel Windsor

If your workplace has a more relaxed dress code, it’s a great opportunity to show off a little of your own personal style and have some fun. Easily recognized by the open throat and tall lacing, the Blucher or Derby boot is an incredibly popular style. It’s also one of the most versatile and wearable boots you can own.

While the structure and construction is the same, Blucher boots typically come with two different types of ornamentation. Sometimes, they simply feature a balmoral cap on the toe. Alternatively, they may be adorned with brogue ornamentation.

Whatever your preference, both styles exude a heritage aesthetic while remaining timelessly stylish. These boots look great with smart pants and jeans, yet can also be worn with certain suits. For instance, brogue boots work wonderfully with a three-piece tweed suit and really push the vintage vibe.

Best boots for casual wear

A Chelsea boot in tan is far more casual than the same boot in black

A Chelsea boot in tan is far more casual than the same boot in black
Image: Bespoke Unit

Boots are particularly versatile footwear and easy to wear casually when the mood takes you. For relaxed weekends, we recommend lighter colors such as brown or tan.

Even the most formal styles like Chelsea or Blucher boots can be worn casually with jeans, which can’t be said of dress shoes. Similarly, you can opt for more rugged boots that feature chunky soles and unique finishes like a moccasin toe.

Otherwise, try boots that incorporate different materials and textures like suede. The Bespoke Unit team is particularly fond of the recent trend for boots that have sections of tweed on the uppers.

 

The Bespoke Unit team loves these leather and tweed boots. Prestige Country Boot in Tweed from Samuel Windsor

The Bespoke Unit team loves these leather and tweed boots
Image: Prestige Country Boot in Tweed from Samuel Windsor

What next?

Now that you’ve read our detailed guide on how to wear men’s boots, why not check out our guide to shoe formality? Otherwise, learn more about how the best boots are made with our shoe construction guide.

More about the author

This article was written by Charles-Philippe Bowles of Bespoke Unit. Their mission is simple: combine encyclopedic knowledge of classic gentleman’s style with current topical content to deliver the most comprehensive, easy-to-search, approachable men’s lifestyle resource on the web. Their aim is to help men improve their style, broaden their horizons, and live their best lives.

Posted in Men's Shoes.

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