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Elevate Your Style: 5 Essential Dress Shoes for Men

The right dress shoes can elevate any outfit, but do you know your Oxfords from your Derbys? Read the article to explore the different types of men's dress shoes and how to wear them.

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1. Oxfords

Oxfords are the quintessential formal dress shoe, known for their classy and elegant design. A key feature of Oxfords is their closed lacing system, where the eyelets are attached under the vamp. This creates a sleek and streamlined appearance.

  • History: Oxfords gained popularity at Oxford University in the 1800s.
  • Style Tips: Pair black Oxfords with a black suit for the most formal occasions, such as black-tie events. For other situations, brown Oxfords paired with a blue suit strike the perfect balance between formal and stylish.

2. Derbys

Derbys are similar to Oxfords but with a notable difference: they have an open lacing system, where the eyelets are attached on top of the vamp. This design provides a more relaxed look and greater comfort, especially for men with high insteps.

  • Formality: Slightly less formal than Oxfords, Derbys are versatile enough for nearly any occasion except the most formal.
  • Style Tips: Derbys can be paired with both suits and smart-casual outfits, making them a wardrobe staple. Choose black or dark brown for business settings, and lighter shades for more casual events.

3. Monk Straps

Monk straps are distinctive dress shoes that trade laces for buckles. Originally worn by medieval monks, these shoes have been a stylish choice since the 1900s.

  • Types: Single monk straps are streamlined and suitable for business wear, while double monk straps are more expressive, perfect for nights out or parties.
  • Style Tips: Pair single monk straps with tailored suits for a sharp, professional look. Double monk straps add a touch of personality to both business and smart-casual outfits.

4. Loafers

Loafers are known for their slip-on ease and versatility, allowing them to be dressed up or down. They are based on moccasins and became popular in the 1950s and 60s as a relaxed alternative to traditional dress shoes.

  • Varieties: Horsebit or Gucci loafers feature a distinctive metal detail across the vamp and are considered the most formal. Penny and tassel loafers are generally more casual.
  • Style Tips: Horsebit loafers pair well with suits for a polished look, while penny and tassel loafers are great for business casual or weekend wear.
Black leather chelsea boots made of genuine leather in classic style on a wooden cut. Close-up. High quality photo

5. Chelsea Boots

Chelsea boots epitomize versatility and can be either dressy or casual, depending on their details and material. These boots feature an elastic side panel, making them easy to slip on and off.

  • Formality: For a dress shoe look, opt for a polished finish and a tapered toe.
  • Style Tips: Chelsea boots in leather pair well with suits and dress trousers, while suede versions are ideal for smart-casual outfits.

Additional Shoe Styles


Brogues are not a type of shoe but a style characterized by decorative perforations. The level of broguing determines their formality: the more broguing, the less formal the shoe.

Cap Toe Shoes

Cap toe shoes have a distinct piece of leather across the toe, providing extra durability and visual interest. They are a common feature in both Oxfords and Derbys.


Wingtips feature an additional piece of leather across the toe in a W shape, resembling bird wings. Often referred to as "full brogues," wingtips are known for their extensive broguing and unique style.


Understanding the different types of men's dress shoes and how to wear them can significantly enhance your wardrobe. From the formal elegance of Oxfords to the versatile appeal of Chelsea boots, each style offers something unique. Choose the right pair to suit your occasion, and watch as your outfit reaches new levels of sophistication.