When it comes to building a timeless wardrobe, footwear is the foundation. Classic men's shoes are more than just functional—they’re expressions of heritage, craftsmanship, and personal style. Whether you're stepping into a boardroom, attending a wedding, or dressing down for the weekend, the right pair can elevate your entire look.
In this guide, we explore the key styles that define classic men’s footwear—from the refined Oxford to the ever-versatile sneaker. Each style holds its own story, form, and function—perfect for gentlemen who value tradition with a modern twist.
Style Breakdown: What to Expect
This compendium walks you through seven essential men’s footwear styles. Each section highlights:
- Origins to understand their heritage
- Key Features to identify each design at a glance
- Styling Tips to help you pair them with confidence
- Standout Picks from our collection to complete the look
Whether you're new to fine footwear or looking to refine your rotation, this guide serves as your go-to resource for navigating classic shoes with ease and expertise.
OXFORDS
Origin: Emerging from Oxford University in the early 1800s, these shoes offered a sleek alternative to the traditional Oxonian boot.
Key Features: Characterised by a closed-lacing system and clean silhouette that complements the natural shape of the foot.
Styling: A staple for formal occasions. Best paired with tailored suits or straight-leg trousers for an elongating effect.
Variations: Styles range from classic plain toes to intricate broguing. A standout option: the Guildhall.
DERBY
Origin: Introduced in the 1850s, the Derby was designed for outdoor wear, especially favoured for hunting.
Key Features: Open-lacing system allows for more room, making it ideal for those with wider feet or higher insteps.
Styling: A wardrobe essential that transitions easily from formal attire to smart casual. Pairs well with suits or cuffed jeans.
Highlight: The Tanner remains a timeless example with its traditional English round toe.
MONK STRAP
Origin: Inspired by monks who adopted buckled footwear for practicality and flair.
Key Features: Fastened with one to three buckle straps, often detailed with broguing.
Styling: A stylish substitute for Oxfords and Derbys. Double monks offer a modern twist, while single monks deliver understated elegance.
Classic Choice: The enduring Monkton is a firm favourite.
LOAFER
Origin: Once crafted as a house slipper for King George VI, it later evolved into a menswear classic.
Key Features: Slip-on design, often finished with details like the Penny’s saddle strap or the Tassel’s distinctive flair.
Styling: Tassel loafers shine in business settings. Penny loafers are weekend-ready. For formal occasions, opt for the sleek Venetian style.
Popular Picks: The versatile Banff penny loafer is a go-to.
CHELSEA BOOT
Origin: A Victorian staple that found new life among 20th-century Mods and The Chelsea Set.
Key Features: Elasticated side panels allow for quick slip-on while preserving a sharp profile.
Styling: Elevate your suit game or add character to casual looks with brogued versions.
Must-Have: Brecon, a sleek, polished finish and a versatile design that pairs effortlessly with both formal and casual attire.
BOOT
Origin: Designed for British soldiers during WWII, influenced by the durable South African Veldskoen.
Key Features: Ankle-height, round toe design with open-laced eyelets for breathability and support.
Styling: Ideal with chinos for a rugged alternative to trainers during warmer months.
Iconic Style: The Osborne, featuring a suede upper and Italian "XL" Extralight ® sole.
SNEAKER
Origin: Evolving from 18th-century ‘plimsolls’, sneakers were coined for their silent step.
Key Features: Known for comfort and variety—ranging in shape, material, and colour.
Styling: Opt for clean, minimalist sneakers with blazers or go retro for a modern streetwear edge.
Versatility: Whether dressed up or down, sneakers bridge all styles. Try the ever-reliable Hemsworth.
Mastering the art of classic footwear doesn’t require an overflowing wardrobe—just the right staples, styled well. With an understanding of origins, features, and best-use cases, you can build a shoe collection that complements every occasion, season, and outfit.
From the distinguished Oxford to the laid-back sneaker, each pair in our range has been crafted to blend timeless appeal with contemporary comfort. Explore the full John White Shoes collection to find your perfect fit—and step into style with confidence.