The right dress shoes in your closet are essential to any man’s wardrobe. Learn about the different styles and how to select the best pair for any occasion. Remember that shoes fit differently than pants, so trying on several pairs is essential to find the best fit. Feet tends to swell throughout the day, so leave room for that.

Chelsea Boots

The Chelsea boot is a relaxed answer to your casual attire and a sophisticated finish to your formalwear. Initially designed for Queen Victoria by her cobbler, J. Sparkes-Hall, the boots were made to be easily slipped on and off thanks to time-saving elasticated sides and a pull tab.

Today, it’s not just Chelsea boots, but different shoe trends 2023 are available in various materials and construction methods, from smooth leather to suede. Look for a pair of shoes with sleek, slim silhouettes and rounded toes (there’s always room in the wardrobe for one more dress shoe rule: no pointy or squared toes). The style is also great for work environments that don’t require full business attire.


The quintessential men’s dress shoe, Oxfords, features closed lacing and comes in various styles. From a classic black cap-toe Oxford with no broguing to a two-tone spectator or saddle shoe, there’s a men’s Oxford dress shoe for every occasion. Typically, black leather Oxford shoes are best for more formal occasions, while brown shoes work well with a range of casual attire. A black leather derby dress shoe is also a staple for business casual attire and pairs easily with jeans and chinos. The ultimate choice, however, is a neutral-colored pair of Oxfords that can be worn with virtually anything in your closet.


Derby shoes are the more casual dress style that pairs well with suits, separates, and jeans. They feature open lacing with the eyelets placed on top of the quarters, and they typically have broguing or cap toes. Plain derbies in smooth leather or sedate colors can be worn with a suit, while vibrant suede versions can bridge the gap between formal and casual attire. They’re also suitable for Smart Casual occasions, though according to Classic Style conventions, oxfords are more appropriate for Black Tie.


Brogues are a style of dress shoe steeped in heritage. Identifiable by their decorative punching and serrated trims, they started as humble country footwear before bringing detailed sophistication to the floors of formal dining rooms. There are four types of brogues (complete or wingtip, semi-brogue, and quarter-brogue) and a wide range of finishes. Full brogues and wingtips have decorative perforations in the toe cap and along its edges, while half brogues lack that level of detail, making them a more casual choice. Try a full brogue with a pair of slim jeans and a button-up shirt, or a half-brogue with a pleated maxi skirt and slouchy t-shirt for an offbeat look that still exudes elegance. They’re also suitable for black tie events and other formal occasions.


Loafers skip the laces of Oxford and Derby shoes to create sleek slip-on shoes in various styles. Depending on their materials and embellishments, they can be casual or formal, like saddles and tassels. The style originated in England from Norwegian shoemakers inspired by the moccasin designs of the Iroquois tribe. They are versatile enough to wear with a suit for work or jeans and a T-shirt for a casual evening. You can even go sockless with these shoes for a more relaxed look; make sure they are no-show socks! Loafers are a classic every man should own. They have a unique backstory with great personalities wearing them!


Having an excellent pair of dress shoes in your closet isn’t just a necessity—it’s an investment. But how can you be sure you’re getting the most bang for your buck? While there are many factors to consider, the best place to start is with the secondary details. Shoelaces and eyelets, for example, are a good indicator of the level of formality in a shoe. For example, dress shoes typically have fewer eyelets than casual shoes, which is why they are less formal. The same holds for the material and sole. Shoelaces should feel snug but not too tight to avoid compression and discomfort while walking.

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