November 30, 2023

Dress shoes for men come at two different speeds. You either love them or hate them. That’s fine. It can be unsafe if you aren’t familiar with formal shoes. There are so many different styles of shoes, including Oxfords, brogues, and other ‘brogueing.’ Dress shoes for men belong in the world of cigars, gentlemen’s clubs, and leather wingbacks.

Maybe not. Even if it’s just for funerals and weddings, every modern man needs at least one pair. It’s all about choosing the right style and taking care of them. We’ll show you how to wear the most popular dress shoe styles and maintain them so they look like they just walked off a Rolex advertisement.

Dress shoes for men

There are many categories of dress shoes for men, including subcategories, sub-subcategories, and cross-overs. We will only go through part of the glossary. These are the most popular styles, which should suit anyone who isn’t a prince.


Oxfords is the most popular type of dress shoe for men. The most common styles are ‘Wing Tip,’ ‘Cap Toe,’ and Plain Toe. This style dates back to English students at Oxford in the 19 thcentury. Students wanted something more trendy and low-cut than the traditional half-boot Oxbridge shoe. Oxfords are recognizable by the ‘closed laces.’ This means the two sides of shoe facings come together under the vamp. Oxfords have a formal look and a slim silhouette because of this. The Oxfords hug your feet.

Oxfords: How to Wear Them

If you’re looking for a business suit, choose a safe color like black, dark brown, or English tan. Stick to black patent leather for black tie tuxedos. Suede or nubuck Oxfords will look more casual. Colorful socks are an excellent way to bring out your personality.


Oxfords are almost identical, and this is why people confuse them. Derby shoes are distinguished by their ‘open-laced’ lacing, attached above the vamp. This gives them a brighter, more casual look. They are also called Bluchers or Gibsons and evolved from sport-hunting boots in the 1850s. Derbys are more suited to wider feet because of their open design. Many people find that they are more comfortable than Oxfords.

Derbys: How to Wear Them

Derbys are just as dressy as Oxfords. However, they tend to be less formal. These guys look odd with traditional suits and black ties. Derbys look best with slim-fit jeans or dress chinos. You can go crazy with your socks. Derby shoes are about texture, personality, and style.


Loafers are available in many sizes and shapes, but they have one thing in common: laces. Or, rather, the lack of laces. Loafers, or slip-on dress shoes for men, were initially designed as casual slippers for King George VI. The loafer style became popular among American business people in the 1960s. The lack of laces makes it easy to identify loafers. They also have an elevated toe seam. There are a variety of loafers, including ‘Penny Loafers,’ ‘Tassel Loafers,’ and Bit Loafers,’ but the choice is primarily based on taste. All slugs fall within the same range in the Formality Scale.

Loafers: How to Wear Them

The material and color of your loafers will dictate the style you choose. Blue suede loafers are less formal than black leather loafers and go better with chinos than suit pants. The more formal a shoe is, the sleeker it looks and the darker its color. You should be able to wear Penny or Tassel Loafers in any business suit.

Ankle Boots

Dress Boots are also known as Ankle Boots. Ankle Boots have a short, laced-up boots. These boots are constructed similarly to Oxfords and Derbys but with a shaft that extends up the ankle. Not all styles are suitable for suit pants. For instance, OLDMAN, with its side zipper, would be better suited to chinos. Dark leather boots like the UTAH and ADAMS can work with the right suit.

How to wear ankle boots

The more rounded the toe is, the less formal the boot will be. Suede and nubuck are also textured materials. A traditional suede shoe is a contradiction. You can wear boots with a suit. Just stick to dark leather and clean lines. The boot shape is an Oxford.

Chelsea Boots

The Chelsea Boot is the last option. These boots are a little different from Ankle or Dress Boots. They originate in Victorian England. Unlike Oxfords and Derbys, Chelsea boots are made of a single leather piece, with elastic gussets on either side of your ankle. The toe is also plain, and they are laceless. Chelsea is known for their sleek, minimalist shape. This is precisely what you want in dress shoes. Dark leather Chelsea boots look great with formal suits and business suits. (Black tie is not acceptable). These boots are an excellent option for the classic Oxfords.

Chelsea Boots: How to Wear Them

The only Chelsea boots that should be worn under suit pants are brown or black leather Chelsea. Suede Chelsea boots can be worn only with jeans or chinos. Socks don’t matter so much (nobody will see them); make sure to hem your suit pants appropriately–you’re looking for that nice, ‘natural’ break—no sagging or billowing fabrics.

What is ‘brogueing?’

Many people mistakenly believe that’Brogues’is a specific type of shoe. This is not true. Brogueing can be found on any shoe. The pattern of perforations on the leather is what brogueing refers to. Brogueing was initially designed to let water drain from shoes during wet weather. (FYI, we do not recommend wearing brogues underwater or in marshes). Brogueing is usually seen on Oxfords and Derbys. However, some dress boots and ankle boots also have them. Wing Tips (notice the distinctive swooping wings on the toe) are another name for ‘Full Brogues. Brogueing is a matter of personal taste. Brogueing is not required for men’s dress footwear, but some men prefer it. A black tie is the only exception. Stick to plain black patent leather shoes without any flashy details.

Care for dress shoes.

Dress shoes for men are expensive, and you want to protect your investment. There’s a guide to shoe care that you can read, but dress shoes require a little extra attention. Buy a pair of cedar-wood shoe trees. Your shoes will keep their shape for years to come. Wearing your dress shoes day in and day out is not a good idea. Leather needs to relax and rest. After every use, you should clean and treat the dress shoes (leather protector spray would be a good start). Store your dress shoes, if you can, in the original shoe bag and away from direct sunlight. Our motto is: Take care of your shoes, and they will take good care of you.

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