Many professionals frequent similar weekday morning routines that consist of rolling out of bed, rummaging through their closet, and contemplating the day’s outfit ahead. A significant change in work attire expectations have brought business casual looks to the fore. Perhaps it was inevitable that workwear would lean into comfortability over formality —think cozy cashmere sweaters, crisp denim pants, and the laid-back-but-luxe derby shoe. 

The appeal is understandable. While acclimating to casualwear after years of a quotidian formal routine is no seamless task, there is something to be said about redefining your personal look and creating a timeless wardrobe for every occasion that transcends beyond your 9-to-5 and can take you where the night goes.

how to style a derby shoe

It all starts with the perfect pair of shoes; versatile ones like the aforementioned derby shoe. My prediction? The style will be on everyone’s shopping list as the quintessential pair to be wearing next time you’re headed into the office or meeting friends for drinks or dinner.

What is the derby shoe?

If you’re not acquainted, the derby shoe is the lesser known version of its counterpart, the oxford shoe.

There is one major distinction between the two: While the oxford style is defined by its closed lacing system, meaning that the eyelet tabs are fully stitched to the vamp, or top of the shoe, and don’t leave any space, the derby style boasts an open lacing system, where the eyelet tab are stitched on top of the shoe’s vamp and can be opened outwards.

men's derby shoe esquivel

The derby’s upper design of the open lacing system offers more flexibility—and, therefore, more comfort—to people with a high arch. The derby shoe is also seen as the more casual option, or at least, the one with the ability to pass as informal, which, in this day in age, is all but the definition of a neo-classic wardrobe staple.

How do you find the perfect pair?

If the past few years have revealed anything about societal fashion preferences, it’s that comfort is high on the priority list. But that new, collective penchant didn’t kill luxury; derby shoes are currently offered by some of the best brands in the business. Find them, ahead.

women's derby shoe esquivel

Price range: Under $200

Hugo Boss

Hugo Boss is a standout brand for its statement pieces that are simple but polished, thanks to a mostly neutral color palette. The brand’s men’s derby shoes in brown and black are made from smooth leather, fully lined, and have an embossed logo.

Price range: $200–$750


J.Crew is where you can get so many great pieces for less, and a pair of derby shoes is no exception. The company is all about elevated basics and offers its Ludrow derby shoe in smooth leather, with Italian insoles with a cork-bed filler that molds to the foot. 

Sarah Flint

Sarah Flint’s beautifully made Mackie x Gravati shoes ooze opulence but are rooted in practicality. They feature a cap toe and femme, webbed trim and satin laces. They’re also armored with extra padding in the soles to keep the feet comfortable and a rubber forepart to prevent slipping in wet weather.

Ready to invest? 

These are mere suggestions to find the best derby shoes in the ever-expanding footwear space. Those looking for something with a relaxed and one-of-a-kind appeal should check out Esquivel; our lace-up derbies are made-to-order and customizable, meaning that you can determine the color, material, and fit before it’s made to be purchased by you.

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