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In my mid-20s, I found myself in search of a particular type of leather lace-up shoe. I had envisioned a dress shoe that could complement jeans or tailoring and embody the aesthetic of some of my favorite British bands. While browsing the garment closet during my early days at Esquire, a plain black oxford shoe caught my eye, and I thought, “This is what I’ve been seeking.” But something didn’t feel, or look, right. It wasn’t until I delved into the intricacies of different leather lace-ups that I grasped the significance of subtle construction adjustments that can alter a shoe’s overall appearance. An oxford was not what I had envisioned; it was a derby.
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Name a more versatile boot than the classic Chelsea. We’ll wait.An oxford shoe, known for its inherent formality, has shoelaces positioned beneath the vamp (the section of the shoe upper covering the forepart of your foot). This design yields a streamlined, dressy aesthetic, making it an ideal pairing for suits and evening wear and thus also an essential building block of a guy’s wardrobe.
On the other hand, the derby strikes a nuanced balance between formality and casualness. Its distinctive construction involves quarters sewn atop the vamp, resulting in an open lacing system on the shoe’s upper. The generally rounder toe of the derby marks a departure from the pointed elegance of oxfords and makes for a more robust silhouette.
While this menswear distinction may be common knowledge for many of our dedicated readers, it provides me with an opportunity to reflect on my youthful naivety, express admiration for my favorite leather lace-ups and highlight some suggestions should you decide to add a pair to your rotation. A derby can take many forms, such as a brogue, a boot, a split toe, a buck, and myriad designer variations. However, for the purposes here, I chose to suggest more polished and streamlined silhouettes. It’s all about the shape.
Personally, I love styling derbies with light-wash cuffed jeans, white socks, and a cardigan sweater, reminiscent of 80’s British indie bands like The Smiths. Their versatility, however, extends to virtually any outfit that demands a touch of effort, be it jeans, chinos, corduroy trousers, and of course, tailoring. Keep them polished or allow an accruing patina from time to time that only serves to enhance their timeless charm. A classic pair of derbies is a wardrobe staple that can be confidently rocked with almost anything and investing in a well-made pair will yield a lifetime of style if properly cared for.
These handsome brown derbies from Mr. Porter’s accessible luxury line, Mr. P, are part of their Everyday Staples collection, intending to serve as foundational building blocks for every guy’s wardrobe. The sturdy Vibram soles on these mean they can handle country roads and city streets alike with ease.
A pair of classic black derbies is a perennial favorite, and few brands excel in this category like heritage English shoemaker Church’s. Crafted from a single piece of leather, these derbies showcase craftsmanship while the chunky, storm-welted double sole and glossy polished finish exude sartorial chic.
Yes, a classic Dr. Marten is technically a derby. These icons have become deeply embedded in our cultural zeitgeist, adorning individuals from all walks of life and inspiring designers from Rick Owens to Comme des Garçons. Whether it’s the distinctive yellow stitching or trademark sole these budget-friendly lace-ups pair with anything and I have a hunch they will never go out of fashion.
These rich, velvety chocolate brown suede derbies from Tod’s epitomize timeless, understated luxury. Made in Italy, the leather sole gives off an air of formality to contrast the soft suede upper. Wear these all winter long with gray wool flannel trousers, cords, or jeans but avoid exposing them to snow or rain without first applying a protector.
Heritage UK brand Grenson has been perfecting the art of handcrafted shoes since 1866. Made in their factory, Grenson’s now-iconic “triple welt” showcases a distinctive stepped, triple-style welt that exemplifies the best of British shoemaking. The result is a visually appealing and uniquely crafted derby that not only stands out but is also built to last.
Alden shoes represent the pinnacle of American quality and tradition in custom shoemaking and are celebrated globally for their craftsmanship. This derby, crafted from breathable shell cordovan, molds to your feet, creating a personalized fit that only improves with age. The slightly rounded shape of the toe is a heritage aesthetic perfected.
These shiny enameled leather derbies from renowned Italian house, Santoni, epitomize luxury craftsmanship. The rich burgundy sheen, the slightly rounded toe, and the chunky sole beckon for it to be worn with jeans on a park stroll or with a suit at holiday parties. Properly cared for, these will be the last derbies you need to purchase.
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