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15 most popular types of classic men’s shoes

Diving into the world of men’s shoes can be as rich and varied as exploring women’s footwear. There’s a spectrum of styles, each with its own distinct character. Today, let’s explore the 15 most popular men’s shoe types, categorized based on how they secure to the foot. It’s a journey through classic footwear that every man should know.

Closed-laced men’s shoes

Closed-laced men’s shoes, such as Oxfords, have the eyelets sewn under the vamp (the front part of the shoe), resulting in a closed and sleek appearance. These shoes are considered more formal and are commonly worn with business attire or suits due to their refined design and polished look.

1. Oxford shoes

Cheaney Lime black toe cap men's oxford shoes

Oxford shoes are classic lace-up shoes recognized for their closed lacing system, where the shoelace eyelets are sewn under the vamp (the front part of the shoe). They typically feature a low heel, exposed ankle, and a sleek appearance. Oxford shoes are known for their formal and elegant style, making them suitable for professional or formal occasions.

2. Wholecut oxford shoes

Carlos Santos 6903 Richard dark brown wholecut men's oxford shoes

Wholecut oxford shoes are a refined and luxurious variation of the classic oxford style. These shoes are crafted from a single piece of leather without any seams on the upper, presenting a sleek and clean appearance. Known for their minimalist and sophisticated look, wholecut oxfords are often considered a symbol of exquisite craftsmanship and attention to detail. They are typically associated with formal attire and special occasions due to their elegant design and high-quality construction.

3. Patent leather tuxedo oxford shoes

Cheaney Kelly black patent leather tuxedo men's oxford shoes

Patent leather tuxedo oxford shoes are a specific type of formal footwear designed for black-tie events or highly formal occasions. They are characterized by their glossy, reflective surface, crafted from patent leather, giving them a distinct shine and sleek appearance. Typically worn with tuxedos or formal evening wear, these shoes add a touch of elegance and sophistication to the overall ensemble. The high-gloss finish distinguishes them from standard leather shoes, making them a standout choice for formal attire.

Open-laced men’s shoes

Open-laced men’s shoes, like Derbies or Bluchers, feature the eyelets sewn on top of the vamp (the front part of the shoe), creating an open appearance. These shoes are less formal than closed-laced ones, making them versatile for both formal and casual occasions. They offer more comfort and flexibility due to their open construction.

4. Derby shoes

Carlos Santos 9381 Gary burgundy toe cap men's derby shoes

Derby shoes, also known as Derbies, are lace-up shoes with open lacing systems where the shoelace eyelets are sewn on top of the vamp. Unlike Oxfords, which feature a closed lacing system, the open lacing of Derby shoes allows for greater flexibility in fit, making them more accommodating for wider feet. Derbies are versatile and can range from formal to casual styles, making them suitable for various occasions.

5. Blucher shoes

Cheaney Deal II mahogany men's blucher shoes

Blucher shoes, owing to their one-piece vamp design, exhibit a seamless appearance with fewer visible stitches, creating a sleek and minimalist aesthetic. This construction, integrating the tongue and eyelets into a singular leather piece across the front, not only provides enhanced flexibility but also contributes to a cleaner and more refined visual appeal.

6. Derby boots

Cheaney Jarrow Chicago tan toe cap men's lace-up boots

Derby boots are a style of boots that share characteristics with derby shoes. They feature open lacing, where the quarters (the sides of the boot) are sewn on top of the vamp (the front part). This design allows for more adjustability and room, making derby boots comfortable and suitable for various foot shapes.

7. Buck shoes

Buck derby shoes

Buck shoes, also known as bucks, are casual derby shoes made of suede or nubuck leather. They often have a distinctive design with a plain front, a lace-up closure, and rubber soles. These shoes typically come in lighter shades like beige, light brown, or light gray, and they are often associated with a more relaxed or casual style.

8. Chukka boots

Cheaney Jackie III mahogany men's chukka boots

Chukka boots are ankle-length boots with open lacing and typically two to three pairs of eyelets. They originated from military desert boots worn by British soldiers during World War II. Chukka boots are characterized by their simple, unadorned design and are usually made from suede or leather. They’re versatile and can be dressed up or down, making them a popular choice for various occasions and styles.

Strap-on men’s shoes

Strap-on men’s shoes are characterized by having closures that typically involve straps or buckles rather than laces. They might have one or multiple straps across the upper part of the shoe, allowing for easy fastening. These shoes vary in style and formality, ranging from casual to more refined options, offering a distinctive look and often a convenient, secure fit.

9. Single monk strap shoes

Cheaney Moorgate black men's monk strap shoes

Single monk strap shoes are a style of men’s footwear that features a single wide strap fastening across the upper part of the shoe, secured by a buckle or a metal closure. They are characterized by their unique appearance, blending elements of both formal and casual styles. Single monk strap shoes are versatile, offering a contemporary twist to classic dress shoes, making them suitable for various occasions.

10. Double monk strap shoes

Carlos Santos 6942 Andrew dark brown men's monk strap shoes

Double monk strap shoes are a type of men’s footwear distinguished by two straps that cross the upper part of the shoe and are fastened with buckles or metal closures. These shoes offer a unique and stylish look, combining elements of both formal and casual footwear. The dual straps set them apart, providing a distinct and often more embellished appearance compared to single monk strap shoes. Double monk strap shoes are versatile and can be worn in various settings.

11. Jodhpur boots

Carlos Santos 4125 Aaron noir shadow jodhpur boots

Jodhpur boots are ankle-high boots characterized by a distinctive strap and buckle fastening system around the ankle. They typically have a sleek, close-fitting design and a low heel. Originating from Jodhpur, India, these boots were originally designed for horseback riding, known for their secure fit and versatility. Today, Jodhpur boots are worn as fashionable footwear, often seen in both formal and casual settings due to their stylish appearance and comfort.

Slip-on men’s shoes

Slip-on men’s shoes, as the name suggests, are footwear options designed without laces or any fastening mechanisms. They are created to be easily slipped onto the foot without the need for tying laces or buckling straps. Loafers and certain types of dress shoes fall into this category. These shoes are often favored for their convenience and are available in various styles, from casual to more formal designs, offering versatility and ease of wear.

12. Penny loafers

Magnanni Milos dark mahogany penny loafers

Penny loafers are slip-on shoes characterized by a strap across the instep, sometimes adorned with a diamond-shaped cutout where a small decorative object (like a penny) can be placed. These shoes were popularized in the mid-20th century and became a staple in casual and semi-formal footwear collections. Known for their versatility, they can be dressed up or down, making them suitable for various occasions.

13. Tassel loafers

Carlos Santos 4210 Carl black men's tassel loafers

Tassel loafers are a style of slip-on shoes featuring decorative tassels at the vamp. Originally introduced in the 1950s, these loafers have become a classic men’s footwear option. They are often crafted from leather and are suitable for both casual and semi-formal occasions. Tassel loafers are known for their stylish and sophisticated appearance, adding a touch of flair to various outfits.

14. Opera pumps / Court shoes

Opera pumps

Opera pumps are a formal type of men’s evening shoes. They are typically made from patent leather and have a low-cut silhouette with a thin band across the instep. These shoes are slip-ons without laces or fastenings, offering a sleek and minimalistic appearance. Opera pumps are commonly worn with formal evening wear, such as tuxedos, particularly for black-tie, white-tie events or formal occasions.

15. Chelsea boots

Cheaney Godfrey plough suede men's Chelsea boots

Chelsea boots are ankle-length boots characterized by their elastic side panels and loop or tab at the back of the boot to aid in pulling them on. They often have a sleek silhouette with a rounded toe and a low heel. These boots originated in the Victorian era and gained popularity in the 1960s. Chelsea boots are versatile and can be dressed up or down, making them suitable for various occasions.