The Holiday Dress Shoes, Deconstructed

If you’re relying on that single pair of Derby’s in the back of your closet to fulfill your formal-wear needs, then we have bad news: there is a wrong way to wear a dress shoe.

Considering that there are dozens of formal footwear options that all fall under the umbrella of “dress shoe”, it’s easy to choose one based solely on looks; unfortunately, this method disregards a few key formal-wear rules that you should know before you add to your cart. To simplify the process, here are the 3 dress shoes that every wardrobe needs—and what makes them different from each other.

The Oxford

Perhaps the most popular choice for a dress shoe, the Oxford is a minimal style that is both versatile and timeless. The Oxford gained momentum in the early 1800s, particularly among students at Oxford University (hence the name), and has been a staple in menswear ever since. This style is characterized by the closed lacing created by the structure of the facing and vamp (the portions of the shoe from the front of the ankle to the base of the toe), this closed look creates a very snug contour of the foot, making the shoe appear long and slim.

Where to wear them:

Oxford’s are popular because of their versatility. You can wear this style with any formal attire and it will look sharp—making this an ideal option for those looking to add just one dress shoe to their wardrobe. Black leather is the safest choice, as these work for tuxedos, business suits, and even more casual day-to-day styles. Brown leather is also an option—though these won’t work in a black-tie setting.

The derby

What makes them different:

The Derby is the Oxford’s more casual younger brother. To the untrained eye, this style can be confused with an Oxford due to its overall look, but the difference between the two changes the structure entirely. The Derby has it’s facing and vamp in the opposite position as that of the Oxford, which creates an “open-lacing” silhouette, for a wider fit. These shoes were originally used as hunting boots, which explains the prioritization of comfort over style.

Where to wear them:

The Derby is not the shoe to wear with a tuxedo or black-tie outfit. The wide silhouette creates a more casual look (the lacing style is more akin to a running shoe than an Oxford), and pairs better with business attire or casual outfits, like khaki pants or tailored jeans. These are a worthwhile purchase for those who wear suits to work or prefer a more elevated look when they’re off the clock.

The loafer

What makes them different:

If you’re looking for something to set you apart, a loafer is a stylish alternative to the oxford in terms of versatility. This style originated from house slippers worn by British royalty, eventually gaining popularity as a formal shoe in North America between the 1930s-’60s. Loafers are characterized by their lack of laces and a lower topline—giving the shoe a slipper-like appearance. Loafers are often decorated with a saddle or metal feature across the facing.

Where to wear them:

Loafers rank nearly as high as Oxfords for versatility; a classic leather pair will work for both a formal event and a dressed-down occasion. The loafer offers the freedom to show your personal style with the socks you choose and the hardware/decoration that’s used on the facing. Gucci is the brand that brought the loafer into the formal menswear world, so you can’t go wrong with a classic pair from the renowned fashion house if you’re looking for an investment piece.

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