In our previous conversation, we delved into men’s fashion, focusing on the five essential suits every man should own. We discussed the versatility of suit colors and the importance of investing in timeless pieces. Now, we shift our attention to another vital aspect of men’s style: shoes.

Just as a well-fitted suit can enhance your confidence and sophistication, the right pair of shoes can take your outfit to the next level.

Shoes are more than just functional items; they are expressions of personal style, reflections of individual taste, and indicators of sartorial expertise. Just as a well-curated wardrobe is essential for navigating different occasions, a diverse collection of footwear is crucial for any stylish man.

In this exploration of men’s footwear essentials, we will journey through the world of shoes, highlighting the key styles that every man should have in his wardrobe. Here are the five essential shoes every man should own:

• Oxford or Derby Shoes

The Oxford shoe, named after Oxford University, has its origins in the 19th century when students transformed the Oxonian half-boot into a formal shoe with closed lacing. By the late 19th century, it had gained popularity among gentlemen for formal occasions. Crafted from premium leather, Oxfords boast a sleek silhouette, making them a symbol of tradition and timeless sophistication.

Today, Oxford shoes are a staple in men’s footwear, offering both classic style and versatility. Their closed lacing system and refined appearance make them suitable for formal and smart-casual events. Oxfords pair seamlessly with suits, dress pants, and chinos, making them ideal for business attire, formal gatherings, and special occasions. They add an element of elegance and professionalism to any outfit, making them an essential addition to any man’s wardrobe.

When considering Oxford shoes, it’s essential to have a pair in black, as it complements all outfits. Additionally, a brown pair is recommended for its versatility, neutral tone, and ability to convey professionalism.

• THE SINGLE/DOUBLE MONK SHOE

Monk shoes have historical origins tracing back to European monks in the Middle Ages, who wore practical sandals featuring closed toes and buckled straps. These functional sandals gradually evolved into sophisticated footwear options. The single monk shoe emerged in the early 20th century as a stylish alternative to traditional lace-ups, while the double monk gained popularity in the mid-20th century for its unique design. Both styles have since remained cherished for their timeless appeal and versatility, making them essential components of a modern gentleman’s wardrobe.

Today, both single and double monk shoes continue to be prized for their timeless appeal and versatility, making them indispensable additions to any modern gentleman’s wardrobe. Now, let’s delve into the details of these iconic footwear styles and discover how they can elevate your ensemble. When it comes to monk shoes for corporate settings, I recommend opting for the brown color, as it always brings a sharp, gentlemanly look that garners admiration.

• THE LOAFER

Loafers have a rich history, originating in the early 20th century when Norwegian shoemakers introduced slip-on shoes. The modern loafer as we know it today gained popularity in the 1930s with G.H. Bass’s introduction of the “penny loafer,” characterized by its distinctive strap with a penny slot. Associated with Ivy League style in the United States, loafers soon gained global popularity for their comfort and versatility. Today, loafers remain a timeless wardrobe staple, available in various styles and materials to suit different preferences and occasions.

Loafers are incredibly versatile and can be paired with a range of outfits for different occasions. For casual looks, pair them with jeans or chinos and a button-down shirt or polo. For a business casual attire, match them with tailored trousers and a dress shirt, optionally adding a blazer. They can even be worn with suits for less formal events. In the summer, pair them with shorts and a linen shirt for a relaxed yet stylish look. Experiment with different styles and materials to suit your personal style.

Overall, loafers offer a stylish and comfortable footwear option for any occasion. The preferable color depends on your personal style, wardrobe needs, and the occasions you plan to wear them for. Consider investing in a versatile pair in a neutral color like brown or black for maximum versatility, and then explore other colors to add variety to your footwear collection.

• SNEAKERS

The history of all-white sneakers dates back to the early 20th century, evolving from the dark-colored canvas sneakers of the late 19th century. The shift to white sneakers began with the introduction of white rubber soles, influenced by changing fashion trends and a desire for a cleaner aesthetic. Initially linked to sports and athleticism, white sneakers soon became fashion essentials, embraced by celebrities and style icons. Iconic designs from brands like Converse, Adidas, and Nike have contributed to their enduring popularity, making all-white sneakers a timeless and iconic footwear choice for people of all ages.

All-white sneakers for men are versatile and can be worn casually with jeans or shorts, sportily with athletic wear, smart-casually with trousers, or for a fresh summer look with shorts and a linen shirt. They offer both style and comfort, making them a must-have in any wardrobe.

• CHELSEA BOOTS

Chelsea boots have a rich history, originating in England in the mid-19th century for equestrian use. They quickly gained popularity among the fashionable elite and later became a staple in mod fashion during the 1960s. Today, Chelsea boots remain a timeless footwear choice appreciated for their sleek design and versatility.

For casual wear, pair Chelsea boots with jeans or chinos and a casual shirt or sweater for a stylish yet relaxed look. For a smart-casual attire, combine them with tailored trousers or slim-fit pants and a button-down shirt or polo for a sophisticated ensemble suitable for various occasions. Additionally, Chelsea boots can be worn with suits for a modern and polished look, especially in more casual or contemporary settings.

What’s your go-to style for Chelsea boots?