Every man’s wardrobe should include a variety of shoe styles to complement different outfits and occasions.

We’ll dive into various types of men’s shoes, exploring key features, and sorting them by style and occasion. Whether you’re looking for a stylish pair to wear to a formal event or a casual shoe for everyday wear, we’ve got you covered. So, buckle up, and let’s step into the world of men’s footwear.

Formal Shoes for Special Occasions

Oxfords

Oxfords, also known as Balmorals in some regions, are traditionally considered the most formal type of men’s shoe. They originated in Scotland and Ireland and were popularized by students at Oxford University in the 1800s, hence the name. The defining characteristic of Oxfords is their closed lacing system, where the eyelet tabs are stitched underneath the vamp, giving them a streamlined and neat appearance.

Oxfords come in various styles, including plain toe, cap toe, and can be made from several materials like leather and suede. They are typically worn with suits and are a go-to choice for formal events such as weddings, important business meetings, or black-tie events. When paired with a well-tailored suit and a classic dive watch, Oxfords can truly elevate a man’s style quotient.

Brogues / Wingtips

Brogues are in the Oxford shoe family due to their lace construction but are distinctive for their intricate perforations and serration along the visible edges of the material. Originally designed in Ireland and Scotland as a functional outdoor shoe, history (or perhaps folklore) contended that the holes allowed water to drain when walking in wet terrain. Whatever the Brogue origin story, they’ve evolved into a stylish choice for both formal and casual settings.

Brogues come in several styles, including full brogues or wingtips, semi brogues, and quarter brogues, each offering a different level of detailing. Full brogues are the most decorated with their wingtip design, while quarter brogues are the most subtle with only a perforated toe cap. Brogues can be paired with suits or tailored trousers, and in more casual settings, they work well with chinos or jeans.

Monk Straps

Monk straps add sophistication with their unique buckle closures. They are available in single or double strap variations and can be worn with a suit or dress pants.

Monk strap shoes are a stylish alternative to lace-ups, known for their buckle and strap closure instead of laces. Named after the monks who originally wore them, monk straps offer a unique blend of style and comfort. They sit comfortably between formal and casual footwear and are available in single or double strap variations.

Monk straps exude sophistication and can be worn with a range of outfits. For a formal look, they can be paired with a suit or dress pants. However, their unique design also makes them suitable for adding a touch of class to a smart-casual outfit. In either setting, a classic dive watch can complement monk straps well, tying the ensemble together.

Dress Loafers

Dress Boots

Dress boots are a versatile piece of footwear that offer a unique blend of the elegance of dress shoes and the durability of boots. They’re typically ankle-length, made of high-quality leather, and have a slim profile that easily fits under dressier trousers.

Dress boots come in various styles, including brogue boots, cap toe boots, and Chelsea boots. They’re appropriate for a wide range of occasions, from office settings to more formal events. In colder weather, they’re a stylish alternative to traditional dress shoes, offering added warmth and protection.

Dress boots work well with a variety of outfits. They can be worn with a suit for a smart, sophisticated look or paired with jeans for a more casual, yet polished outfit.

Dress Cowboy Boots

Casual Shoes for Everyday Wear

Sneakers

Sneakers are a versatile choice for casual attire. They come in various styles, such as:

• Low-top
• High-top
• Slip-on
• Athletic-inspired
• Ideal for pairing with jeans, shorts, or casual trousers

Loafers

Loafers are a timeless option for a laid-back look. They come in different styles, including:

• Penny loafers
• Tassel loafers
• Horsebit loafers
• Driving loafer
• Great with chinos, jeans, or dressier shorts

Boots

Boots offer comfort and durability for various casual settings. Some popular styles include:

• Chelsea boots
• Chukka boots
• Desert boots
• Work boots
• Can be paired with jeans, chinos, or tailored trousers

Chelsea boots

Chelsea boots are an iconic type of boot with a history dating back to the Victorian era. They are characterized by their ankle-high design, close-fitting nature, and an elastic side panel which allows for easy slip-on and slip-off. Some versions also include a handy pull-tab on the back of the boot.

Made popular in the 1960s by the Beatles, Chelsea boots have a simple yet sophisticated design that makes them versatile for both casual and semi-formal occasions. They can be found in a variety of materials, with leather and suede being the most common.

Chelsea boots can be paired with a variety of outfits. With a suit, they offer a stylish, contemporary alternative to traditional dress shoes. For casual occasions, they look great with jeans or chinos. Add a sleek dive watch to complete the look with a touch of sophistication.

Chukka Boots

Chukka boots have a history connected to both polo and the military. They are ankle-high boots with suede or leather uppers, open lacing with two or three pairs of eyelets, and typically a leather or rubber sole. The name ‘chukka’ likely comes from polo, where a chukka is a period of play.

These boots are known for their simple, unadorned design, which lends itself to versatility. Chukka boots can be dressed up or down, making them suitable for both casual and smart-casual occasions. They’re often seen in neutral tones like beige, brown, and black, which easily complement various outfits.

When wearing chukka boots, pair them with casual or business casual outfits. They go well with jeans, chinos, and even some suits. With a pair of chukka boots, a matching belt, and a stylish dive watch, you’re ready for a wide range of occasions.

Desert Boots

The desert boot owes its origin to the footwear worn by British soldiers stationed in desert regions during World War II. This boot was designed for durability and comfort in harsh desert conditions, featuring a simple design constructed from suede or beeswax leather with a crepe sole.

Desert boots are indeed similar to the chukka boot in reversed leather, ankle-high, with 2 or 3 eyelets construction, but desert boots different leather and sole material geared towards desert conditions.

The style gained mainstream popularity in the 1950s when Nathan Clark, a descendant of the founders of the British shoe manufacturer C&J Clark, introduced his take on the boot. Inspired by the military footwear he saw while serving in Burma, Clark’s design quickly became a classic. Over the decades, the desert boot has maintained its appeal, admired for its practicality, comfort, and timeless style.

Work Boots

Modern work boots have their roots in the industrial revolution of the 18th and 19th centuries, when workers needed sturdy, protective footwear to prevent injuries in hazardous environments such as factories, mines, and construction sites. Early work boots were often heavy, knee-high leather boots with a high heel to secure the foot in stirrups or climbing irons.

The evolution of work boots is closely tied to advancements in technology and materials. With the invention of vulcanized rubber in the mid-19th century, waterproof boots became more widely available. Steel-toed boots, which provided better protection against falling objects, became standard in many industries in the mid-20th century.

In the latter part of the 20th century, new materials and technologies allowed for the creation of work boots that were not only protective but also more comfortable and lightweight. Advancements in synthetic materials and manufacturing processes have resulted in work boots that are resistant to chemicals, electricity, and extreme temperatures.

Modern work boots now come in a wide variety of styles, including lace-up boots, pull-on boots, and even athletic styles, to suit the needs of different professions. Features such as waterproofing, insulation for cold conditions, and breathable fabrics for hot environments, have become common.

While work boots are designed with functionality and protection in mind, their rugged appeal can be leveraged to create stylish casual outfits. Work boots pair exceptionally well with denim. For a balanced look, opt for slim-fit or straight-leg jeans that will sit nicely over the top of your boots. Avoid skinny jeans as they can create a disproportionate look with the chunkiness of the boots. Flannel shirts, simple t-shirts, or henley shirts are excellent choices to pair with work boots for a laid-back, casual look. For a more rugged appeal, try layering with a leather jacket or a denim jacket.

Cowboy / Western Boots

Ambassador Times hails from Texas so we would be remiss to neglect a time-honored favorite. The western boot varies in its acceptability and normalcy in certain parts of the country, but here in Texas it’s very common to see men wearing cowboy boots. We’ve personally seen cowboy boots worn in business casual attire in places like Austin, Atlanta, and Nashville.

Tips for Men’s Shoes

Certainly, there are several factors to consider when buying, wearing, and caring for men’s shoes. Here are a few key points:

When Buying:

1. Fit: Make sure the shoes fit well. The right shoe should feel comfortable from the moment you put it on. In our experience, it’s not worth it to buy shoes assuming they will “stretch” out significantly more after breaking them in or even using stretchers.
2. Material: Check the material of the shoe. Leather is often considered more durable and stylish for formal shoes, whereas synthetic materials may be suitable for athletic shoes.
3. Brand Reputation: Research the brand to ensure they produce high-quality, durable footwear.
4. Style: Choose a style that suits your wardrobe and lifestyle.
5. Versatility: Consider how versatile the shoe is – can you wear it with multiple outfits and to various occasions?

When Wearing:

1. Appropriate for the Occasion: Ensure the shoe style is appropriate for the occasion or setting.
2. Comfort Over Long Periods: If you’ll be standing or walking for extended periods, prioritize comfort. Add shoe in-soles to help make uncomfortable shoes more comfortable.
3. Pairing with Outfits: Make sure the shoes complement your outfit well. Generally, the color of your shoes should match or be darker than your pants.
4. Weather Conditions: Consider the weather. Leather shoes may not be the best choice for rainy weather, while boots might be too warm for summer.

Caring for Shoes:

1. Regular Cleaning: Clean your shoes regularly to remove dirt and prevent damage.
2. Proper Storage: Store your shoes in a cool, dry place to prevent mold and mildew. Using a shoe tree can help maintain their shape and minimize creases in the material.
3. Polishing: Regularly polish leather shoes to keep them looking their best. One of our favorite tips is to go to the men’s shoe department in Nordstrom. They offer shoe polishing for a reasonable price.
4. Rotation: Avoid wearing the same pair of shoes two days in a row. This allows them to air out and helps extend their lifespan.
5. Repairs: Address any damage immediately to prevent it from worsening. This could include replacing worn-out soles or fixing loose stitches. Be sure to find a reputable shoe repair shop nearby and get to know them well.

Remember, investing in a high-quality pair of shoes and caring for them properly can ensure they last for years.

Final Thoughts

A well-rounded shoe collection is essential for every man, as it enables you to dress appropriately for any occasion. With this guide, you now have a solid understanding of the various types of men’s shoes and their key features. Don’t forget to pair your chosen shoes with a timeless accessory like a dive watch to elevate your style even further.

FAQs

What is the difference between Oxfords and Derbies?

The main difference between Oxfords and Derbies is the lacing system. Oxfords have a closed lacing system, while Derbies feature an open lacing system.

What is the difference between Oxfords and Brogues?

The terms “Oxford” and “brogue” describe different aspects of a shoe. “Oxford” refers to the lacing system of the shoe, while “brogue” describes the decorative perforations. You can have an Oxford shoe without broguing, a brogued shoe that isn’t an Oxford (like a brogued Derby), or an Oxford shoe with broguing (an Oxford brogue).

How do I choose the right shoe size?

To choose the right shoe size, measure your feet and consult the manufacturer’s sizing chart. Also, consider the width of your feet, as some brands offer wide or narrow sizes.

How do I maintain my leather shoes?

To maintain your leather shoes, clean them regularly with a soft brush or cloth, apply a leather conditioner, and store them in a cool, dry place away from direct sunlight. Using a shoe tree can also help maintain their shape.

How do I choose the right type of shoe for an occasion?

Consider the dress code and environment of the event. For formal occasions, opt for Oxfords, brogues, or monk straps. For casual settings, sneakers, loafers, or boots are suitable choices.

Can I wear a dive watch with formal shoes?

Yes, a dive watch can be worn with formal shoes as its classic design and sophisticated appearance make it suitable for both formal and casual settings.