Founded in 2008, Hockerty is the e-commerce leader in custom suits and custom dress shirts, as we offer our customers complete freedom to design their own clothes by choosing from a wide range of styles and fabrics. 
Are you all ready to head out for that event, dressed from head to ankles? Yes, you are right, we intentionally did not say toes. Because your shoes must be included in the perfect outfit if you want to look flawless. Shoes can easily make the difference between shabby and chic and make or break your perfectly polished outfit. Take care of what you are wearing on your feet and you will ace that interview or date easily.
Just to mention the important fact at the beginning: you should not buy your new dress shoes without any prior shoe knowledge. The right dress shoes must fit you perfectly, should be made 100% out of durable leather and be properly stitched to avoid a short-lived life.
The popular claim is that you need five men’s dress shoes in your wardrobe that will transform you into an elegant man and will make you confident in the office or at events. Find these five types of men’s dress shoes you should own and let the transformation begin.
Oxford Shoes
Oxford shoes are the most common type of men’s dress shoes. You can see them being worn basically everywhere – to the office, to a wedding or sometimes even combined with chinos for a casual night out. Their main standout feature is a closed lacing and low heel, making them look elegant and clever. Black Oxford shoes are mainly appropriate for high-end events, while brown-colored Oxfords might be worn to any other occasion that calls for some level of formality.
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| Shiny Tuxedo Oxford Shoes | |
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| Italian Calf Oxford Shoes | Brown Suede Oxford Shoes |
Derby Shoes
Derby shoes are very similar to Oxfords but have one main feature that distinguishes them: Derbies have an open lacing system. Like all the other men’s dress shoe types, they also come in many variations and colors, but the lacing always remains open. Derby shoes are only suitable for casual events and you should not wear them for very formal occasions.
Find more differences between Oxfords and Derby shoes here.
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| Blue Suede Derby Shoes | Black Derby Shoes |
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| Brown Leather Derby Shoes | Blue Derby Shoes |
Monk Straps Shoes
Monk Strap – as the name suggests – is a dress shoe type without laces. Instead, they have a strap across the upper top of the shoe and a buckle to close it. These straps make them fall into the semi-formal category, ideal for a day at the office. One-strap version and two straps (called double-monk) are the most widely worn choices. Monk Straps are still very eye-catching which makes them popular among refined gentlemen that want to look unique.
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| Brown Double Monk Strap Shoes | Black Double Monk Strap |
Brogue Shoes
The name Brogue shoes comes from the broguing technique, used to perforate the upper part of a shoe to create a decorative ornament. Broguing can be used on all of the dress shoe types mentioned (Oxfords, Derbys, Monks) and depending on the perforations, we differ between full brogue, semi- brogue and quarter brogue. The only rule: the more broguing, the less formal the Brogues are.
Wingtip Shoes
Wingtip is another semi-formal choice for work but can also be worn as a high-end variation for your tuxedo night. Its key feature is a cap toe shaped like wings, often perforated with broguing. The color rule is similar to with Oxfords, black Wingtip shoes are mostly preferable for formal occasions, whereas brown Wingtip is for casual days.
Recent years have brought a comeback for this unique type of dress shoe, so be sure to find yours to complete your dress shoe collection with them.
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| Wingtip Double Monk Shoes | Black Suede and Leather Wingtip Shoes |
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| Brown Suede and Leather Wingtip Shoes | Brown Leather and Tweed Wingtip Shoes |
Cap Toe Shoes
Cap Toe should maybe not be introduced as a separate group but rather as a version of other dress shoe types. Cap Toe shoes feature individually sewn leather in the toe part which is separated from the rest of the upper leather part (called vamp). This provides extra protection for the sensitive part of the shoe while wearing them daily or when travelling, but also gives an appealing look to Monks, Oxfords or Derbys.
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| Cap Toe Double-Monk Strap | Cap Toe Blue Leather and Tweed |
Wholecut Shoes
If you want to go for a very clean appearance, Wholecut shoes are the best choice for you. They are cut and made from a single piece of leather and need to be produced by skilled shoe artisans. Wholecuts are not considered very formal, mostly thanks to their non-traditional form.
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| Brown Wholecut Shoes | Black Wholecut Shoes |
Men's Loafers
Among the staple footwear that every gentleman must have in his closet is the classic loafer. What are loafers? Loafers are a slip-on style of shoe that is usually constructed in leather or suede. It does not feature any laces, fastenings or other types of closures. It’s a low-cut shoe with a flat heel and a thin leather sole. A loafer is a shoe style that one can easily slip his foot in and out of.
Tassel loafers
Tassel loafers is a very common and modern type of loafers gentlemen wear today. They feature tassels sitting on the shoe vamps and are most traditionally made from suede.
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| Blue Suede Tassel Loafer | Brown Tassel Loafers |
Penny loafers
The adaptable nature of the penny loafers and its availability in a wide range of colors and materials, makes it the perfect style to wear whether professionally or casually. As such, they are favored by men of varying ages and varying style preferences.
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| Black Leather Penny Loafers | Brown Leather Penny Loafer |
Horsebit loafers
The horsebit loafers are also known as Gucci loafers, as the house of Gucci was the one who invented them. They are a luxurious style coming with different colored metals and can be customized to make you stand out of the crowd.
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| Horsebit Loafer White Leather | Brown Horsebit Loafer |
We hope that you've learned the most basic and important men's dress shoe types and you will be able to find the best ones for you. Don't forget that at Hockerty, your shoes are always custom made. They are made of 100% Italian leathers and produced in Spain to your measures. Find more in our collection:
If you want to learn more about men's boots types, read our guide here. Or you can try designing your custom boots for men directly.
See more:
- Our Chukka Boots
- Our Chelsea Boots
- Our Dress Boots