Robb Recommends: How This Old-School Lace-up Set the Gold Standard for Dress Shoes
Welcome to Robb Recommends, a regular series in which our editors and contributors endorse something they’ve tried and loved—and think will change your life for the better.
When I first began working at Esquire, I was on a mission to upgrade my leather lace-ups. I wanted a pair of shoes with a distinct shape—versatile enough to wear with both jeans and tailoring, and, importantly, something that captured the aesthetic of my favorite British bands. One style that kept catching my eye was the Church’s Shannon. Few leather shoes embody timeless style, impeccable craftsmanship, and rich heritage quite like it. As I dug deeper, I discovered what sets it apart: an exceptional leather finish, Goodyear construction, thoughtful design, and a substantial heft that imbues it with longevity. It’s refined, versatile, and sophisticated—all hallmarks of its DNA. But above all, it’s the silhouette that drew me in. Polished, streamlined, and endlessly elegant, the Shannon is a last that has stood the test of time. As the Shannon recently celebrated its 50th anniversary—a milestone for any single shoe model—it feels fitting to pay homage to this iconic derby and reflect on why it remains a worthwhile investment. Decades later, its appeal hasn’t waned—and I doubt it ever will.
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Church’s Knows Its Craft
When debating the top five heritage shoemakers of all time, Church’s is undoubtedly in that conversation. This storied British cobbler embodies history and craftsmanship, producing some of the finest leather shoes in the world. Beloved by classic menswear aficionados, street-style enthusiasts, countryside goers seeking durability, footwear connoisseurs with an eye for detail, Brit rockers, and even James Bond himself, Church’s holds an esteemed place in the footwear pantheon. Tracing back to 1675 in Northamptonshire—a region renowned for leather craftsmanship—Church’s helped transform shoemaking by adopting the Goodyear welt method, solidifying the reputation of early English ready-to-wear shoes. Each pair, including the Shannon, is still handcrafted in Northampton by expert artisans through an intricate weeks-long process that can involve 250 manual operations. First introduced in 1974 and named after a town in western Ireland, the Shannon stands as a benchmark of artisanal excellence—a gold standard for derbies and a testament to Church’s enduring craft.
A Quick Detour on Derbies
The defining feature of a derby is its open lacing system, where the quarters (the side panels) are sewn atop the vamp—the part of the shoe covering the forefoot. This contrasts with the more formal Oxford, which features a closed-lacing design where the quarters are sewn beneath the vamp. This open construction is what gives a derby an aesthetic balance between dressy and casual. Unlike the sleek, pointed elegance of Oxfords, derbies often have a rounder toe and a more robust silhouette for a more approachable yet still refined vibe. While many of our well-versed readers are likely familiar with these distinctions, it’s worth revisiting why the derby has endured as a menswear staple—and why, in my view, the Church’s Shannon epitomizes the ideal variation. Allow me to wax poetic on why.
Color and Shape
What first drew me to the Shannon was its shape. Having spent many years working in the shoe market, I’ve seen more leather lace-ups than I can recall, but even from across the room, the Shannon stands out with its distinctive silhouette and minimalist luxury. It’s crafted from a single piece of leather—a testament to its craftsmanship, as it demands the highest-quality hide. While many derbies strive for a streamlined last, they often fall short—either too tapered at the toe or too clunky. The Shannon, however, walks its own walk. Built on Church’s #103 last, it features a slightly higher instep and a subtly wider fit, resulting in a toe shape with just the right roundness. It’s a nod to traditional English country style but adapted to modern dress shoes. Slightly tapered for refinement yet rounded for rugged wear, it’s always stylish and in its element, no matter the occasion.
Perfectly Polished Binder Leather
Originally designed as a versatile dress shoe for navigating rainy London streets, the Shannon was crafted using Polished Binder Calf—a water-repellent leather that combines durability with an elegant, glossy finish. This unique resin-treated leather prevents color fading, resists cracking, and improves with age, developing a rich patina. While all leather shoes naturally crease with wear—a charming characteristic that tells their story—this leather is easy to polish and will last a lifetime with proper care. The broader Shannon collection features an array of rich hues, including black, sandalwood, and navy, each with a depth and dimension that shifts subtly in the light. I’m partial to the rich burgundy jewel tone that looks equally at home with light-wash jeans or gray flannel tailoring.
Construction and a Last That Lasts
Hold the Shannon, and you’ll notice its impressive heft—this shoe feels very robust and substantial. Church’s craftsmanship shines here, showcasing the Goodyear welt in all its time-tested glory. This technique involves stitching the upper, insole, and welt together, creating a durable structure that can be easily resoled. Its unique “all-around welt,” with outstitching that encircles the shoe, adds to its sturdiness. The Shannon also features a storm welt, an added layer of protection that forms a tighter seal between the upper and the sole to keep water out. That said, these lace-ups make you earn their comfort. They will likely feel stiff at first due to the robust construction, but with repeated wear, they’ll mold to your feet and become uniquely yours.
The Derby is in the Details
A discerning eye will appreciate the finer details of this derby. Smooth and sleek, its upper is elevated by artisanal touches—most notably, the hand-stitched half-moon motifs on the eyestay, which reinforce the wings and are a mini aesthetic trademark. The tongue comprises soft-textured Nappa leather on its sides—hidden when worn—for flexibility and a smoother on-and-off. Inside, the shoe is fully lined for durability, while handwritten details mark each model, adding a personalized touch to its already handcrafted charm.
Versatility Abounds
Perhaps the most practical feature of the Shannon lies in its versatility—you can wear them with virtually anything. They add a touch of edgy elegance to polished looks like wool flannel trousers, corduroy tailoring, or even a three-piece suit. At the same time, they elevate casual ensembles when worn with jeans or robust heritage chinos. The Shannon is trend-proof but adapts to most au courant silhouettes or styles. They pair beautifully with voluminous wide-leg or pleated trousers, grounding them with heritage charm and are equally at home with slim black jeans or a sharply tailored suit for a sleeker, moodier vibe. Personally, I love styling the Shannon with cuffed light-wash blue jeans, white socks, and a cardigan—a nod to the effortlessly cool style of 1980s British indie bands like The Smiths.
With proper care, the Shannon will provide a lifetime of style, and no matter how you wear them, they will be as relevant in 2025 as they will be in 2095. They are a foundational investment that deserves a spot in any well-curated wardrobe. The Shannon isn’t just a derby—it’s the GOAT of derbies, a shoe built to stand the test of time.
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