Style Guide

The 5 Classic Dress Shoes Every Gentleman Should Own

You can’t make a first impression twice. With your shoes as the sartorial window to your soul, it’s important to consider what they say about you. Recent research showed that strangers could accurately predict a person’s age, salary based on their style of shoe and it’s no secret that one of the first things a woman notices on a potential suitor is his shoes. Here are the classic men’s dress shoes that every discerning gentleman should have in his wardrobe.

The Oxford

During the 17th century, men’s footwear was predominantly boots. It’s arguable but commonly thought that in 1825 Oxford University students rebelled against the traditional knee highs and created the Oxtonian Shoe. The characteristics of the modern-day Oxford are in its specific method of construction with a closed lacing system, exposed ankle and low heel. The style is perhaps the most classic of all men’s dress shoes and a deserved place as a wardrobe staple. The Oxford is usually considered a more formal shoe and works well for formal occasions like work, weddings and job interviews. Although one can play around with textures and leathers, it is wise to keep your Oxfords sophisticatedly stylish in traditional hues such as brown and black.

15 by Powell - Oxford PatinaThe ‘15 by Powell unique wooden-like effect is the result of a careful and precise patina technique painted by hand. Crafted with supple calfskin leather, these oxfords breathe tradition and heritage. Wear with a classic single-breasted suit for timeless elegance.

The Derby

The ultimate all-rounder, the Derby is known for its casual, comfortable style, an appropriate dress shoe for every day. The Derby originated in the 1850’s as a sporting shoe and boot for the country until the 20th century where it became a popular style for gentlemen in the city. The main difference between the Oxford and Derby is the seam of the vamp that is made under the quarters, creating an open-faced lacing system. This subtle detail gives the Derby the extra edge in being a slightly more informal style. 

15 by Geerts - Derby Full Brogue
The 15 by Geerts is the perfect statement for the modern gent who’s not afraid to mix and match. Combining soft sand shades with a bold navy blue heel, the ‘15 by Geerts is a full brogued Derby handcrafted with calf leather and suede. Match your pair with a navy suit for a formal look, or with chinos for weekend excursions.

The Monk Strap

The origin of the Monk strap dates back to the 15th century, worn by European monks who embraced the style for inherently practical reasons, as a closed toe version of the traditional monk sandal. Despite the shoe’s humble origin, the style has since evolved to become an integral part of any discerning modern gentleman’s wardrobe and can be worn from the boardroom to bar with effortless ease. Although the single strap is in general the more prominent, the double strap has the fashion edge. Add a dash of Sprezzatura by unbuckling the top strap.

15 by Grant - Monk strap patina Try undoing the top buckle on these top capped Monk straps and watch them do their magic. A playful twist on an otherwise conservative shoe, the hand-painted grey patina adds both a vintage touch to the shoe and an easy-going feel to your wardrobe.

The Loafer

Although more commonly associated with the iconic preppy style of Ivy Leaguers, the loafer began as a shoe worn by Norwegian fisherman in the 1800s, then adopted by English and American designers. The not so humble slip-on is the perfect casual option for warmer months and when you want to elevate your usual style uniform. A pair in calfskin leather is always a suave option when paired with jeans or chinos. A point of contention is should the loafers be worn with or without socks, but throw caution to the wind and wear without for added style points.

15 by Luke

The ‘15 by Luke is your traditional dress shoe. The finesse of the whole cut leather brings out the class in your outfit, in a warm tone of brown. Just slip them on before that important meeting, and even if you didn’t prepare, at least you’ll look confident.

The Boot

Another smart casual style that deserves a place in your wardrobe. A full brogued chukka boot is an unexpected but refreshing pairing for a dress suit and extremely versatile to incorporate into an everyday look. The name ‘chukka’ is thought to come from the game polo, where chukker is a period of play.

15 by Maddox - Patina Boot A full brogued Chukka with a beautiful camel patina finish. The crisp brogue detailing in rich mahogany brown gives this Chukka boot a luxury feel which works well for the weekday or weekend.

Here’s to good health, good principles and above all, good shoesMr. Undandy