Choosing Dress Shoes For Men

Laura Tolentino

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Men wear shoes for various reasons, with fit and comfort being of primary concern. Ill-fitting dress shoes not only cause discomfort, but over time may damage feet over time.

Leather shoes tend to stretch with wear, so an initial snug (but not tight) fit is ideal.

Plain Toes

One of the cornerstones of any gentleman’s wardrobe is an effective pair of dress shoes. No matter if it’s for work, a special occasion, or simply to impress clients – having the appropriate pair can make or break an outfit! Selecting appropriate dress shoes may not be straightforward though as many details need to be considered before making an informed decision; one key aspect being the toe which comes in plain and cap toe varieties that help determine which pair are right for your needs.

Plain toe dress shoes have no decorative detail on their front, making it more formal for formal events, such as suits. But they’re great everyday wear too – great with multiple outfits! And available in various colors and materials so they make for versatile options to meet every need and occasion.

Even though these dress shoes are more formal than cap toe dress shoes, they can still be worn casually with jeans or khakis for casual events. Additionally, they make an ideal addition to office wear as they pair nicely with both business suits and polo shirts.

Loafers are a more casual style of dress shoe that can be worn with anything from suits to jeans. Often flat with an open lacing system and available in various materials and colors – most commonly without broguing or decorative stitching – however more ornate designs may also exist.

Cap Toes

Cap toe dress shoes are distinguished by the addition of a piece of leather covering the front vamp of each shoe and stitched securely into place, creating an artificial border between the toe box and other aspects of its exterior. In some instances, this stitching pattern forms one horizontal line or forms a W-shape from its center of toe.

This design adds an air of formality to dress shoes, making them ideal for black tie events and more formal events. However, black cap toe oxfords are highly versatile shoes and can be worn with various formal outfits as well as smart casual looks – with its eye-catching toe cap drawing great attention from others nearby.

Cap toe dress shoes remain comfortable despite their formal nature. Their looser fit doesn’t necessitate tight lacing like other dress shoe styles do and less likely rub against socks when walking.

Cap-toe dress shoes offer another great advantage: their versatility. From seasonal variations like tan and burgundy hues, through classic black and brown hues.

Cap toe dress shoes are timeless classics every man should own in his closet. Perfect for formal occasions ranging from morning dress to a dark business suit, and also great when worn casually with trousers and blazer.


Wingtip shoes offer the versatility of dress shoes that can be dressed up or down for any occasion, making them the ideal option. Featuring a low band of leather that extends outward from the toecap to create an “wing,” these versatile shoes often have decorative perforations (called broguing) running along their seams for an eye-catching touch. Available in various colors from traditional brown and tan to black, blue and burgundy/oxblood red; most men opt for classic brown as the most preferred pair (like model Twiggy did back then).

Wingtip shoes tend to be more casual than other dress shoe styles, making them suitable for smart casual attire when worn with sports coats and slacks, although jeans with a shirt also work nicely when going for a relaxed look. Since wingtips fall between formal and casual dress shoes, weddings or other formal events like funerals may require them, as a more subdued appearance might not suit.

When selecting wingtips, keep ornamentation and leather use in mind when making your selection. In general, the more ornamentation and lighter shades of leather used, the less formal your shoe will be. In addition, it is wise to think about whether full brogues or semi-brogues would best suit your look; either can be dressed up depending on how they’re styled.

Beyond wingtips, there are other dress shoes you should consider adding to your collection. Cap toe shoes offer another professional option that pairs nicely with most business casual looks.


Oxford shoes represent the formal end of dress shoe spectrum. First popularized by students at Oxford University over 200 years ago, Oxfords remain an elegant option when you need to look your best. Their closed lacing system is stitched directly under the vamp for a tight, close fit that provides sleek elegance – perfect for business attire, weddings or black tie events alike.

Always have a pair of black oxfords in your closet; they are versatile enough to wear with everything from suits for formal events to jeans or chinos for smart casual looks. For added sophistication in everyday style, brown leather oxfords can add elegance; these shoes look great worn alone as well as with jeans, chinos, and sport coats!

If you prefer more casual styles, whole cut or semi-brogue Oxfords could be ideal. While not as extravagant as cap-toe oxfords, they still add a sense of class to any look. Saddle shoes or two-tone spectators could also serve as alternative casual options.

When buying Oxford shoes, be sure you purchase the appropriate size. They tend to run true to size; however, in order to find your ideal fit you may require measuring your feet. Dress shoes have slightly different dimensions from sneakers so the most important aspect when purchasing these dress shoes should be finding something comfortable which does not rub or rub against your feet.


The captoe adds an innovative edge to traditional Oxford shoes, marrying tradition with contemporary. This distinctive feature divides the vamp piece in two, providing for dual-tone shoes – making these captoe oxfords perfect for modern gentlemanly attire such as luxury suits or sophisticated formal wear.

This category of dress shoes is reserved for connoisseurs and enthusiasts, who appreciate both its exquisite details and incredible value proposition. Though costly, if cared for properly these can last decades. Pair yours with burgundy socks, grey fresco trousers, an oatmeal sports coat, and blue-and-white university stripe shirt and you will be ready for anything life throws your way from office meetings to boardroom meetings and beyond!