On Dress Shoes: Oxford, Derby, Loafer, and Double Monk

The serious dress shoe descends from a few canonical forms developed in Britain and France between the late eighteenth and the late nineteenth centuries. The Oxford was refined at the university of its name in the 1830s. The Derby, originally a hunting shoe, was adapted to the city in the same decade. The Loafer arrived from Norway by way of America in the 1930s. The Double Monk is a twentieth-century elaboration of an older monastic form. Each has a specific construction and a specific use, and the four together cover almost everything a tailored wardrobe asks of its shoes. 

The Oxford 

The Oxford is the dress shoe in the strictest sense. The defining feature is closed lacing — the lacing flaps are sewn under the vamp, producing a clean V at the throat of the shoe rather than a separate flap. The closed lacing gives the Oxford its lower profile and its formal line. The most formal version is the plain-toe Oxford in black calf, with no broguing and no cap; this is the correct shoe for black tie, white tie, and the most formal business wear. The cap-toe Oxford — a horizontal seam across the toe — is slightly less formal and the more useful daily Oxford. A wholecut Oxford, made from a single piece of leather without a toe cap, is the most refined of the family and reads as a quietly luxurious choice. 

An Oxford in black calf is the correct shoe for a charcoal or navy suit at any formal occasion. An Oxford in dark brown is the correct shoe for almost every other suit a man owns. The Oxford is the shoe a man builds the rest of his collection around. 

The Derby 

The Derby has open lacing — the lacing flaps are sewn on top of the vamp rather than under it, producing visible flaps that fold over each other when tied. The open lacing makes the Derby slightly less formal than the Oxford, and slightly more accommodating on the foot; the open construction allows the shoe to be loosened more fully, which suits a higher instep or a wider foot. A plain-toe Derby in dark brown is the more relaxed sibling of the Oxford and crosses easily between business and the more casual end of tailoring. A Derby in black is rare; the form reads better in brown leather, and a black Derby occupies an awkward space between the formal Oxford and the more casual brown Derby. 

The Loafer 

The Loafer is the slip-on, with no laces and no buckles, designed to be stepped into rather than tied. The penny loafer, with a small strap across the vamp pierced by a coin slot, was developed by G. H. Bass in 1936 and became the canonical American loafer. The bit loafer, with a horsebit ornament across the vamp, was introduced by Gucci in 1953 and became the canonical luxury loafer. The tassel loafer, with leather tassels at the throat, was developed for Paul Lukas in the late 1940s and became the canonical East Coast loafer. 

A loafer is correct with most suits and sport coats outside the most formal business contexts. A black bit loafer with a navy suit is one of the most useful pairings in modern menswear. A brown penny loafer with grey flannels and a sport coat is the canonical American look. The loafer is the right shoe for the man who spends his life in airports and lounges; the man whose dressing is more formal will own one pair of loafers among several pairs of laced shoes. 

The Double Monk 

The Double Monk closes with two buckled straps across the vamp rather than laces or a slip-on. The form is a twentieth-century elaboration of the single-buckled monk shoe worn historically by monastic orders. The double monk in dark brown is the most stylish of the four shoes and the least conservative. It crosses comfortably between business and dressier sport-coat contexts, and reads as informed without becoming costume. The black double monk reads more formally and is the right alternative to a black Oxford in business wear where a man wants slightly more visible detail. 

What to own 

A complete dress-shoe wardrobe for a man with a serious suit collection is four pairs: a black cap-toe Oxford, a dark brown Oxford or Derby, a brown loafer, and a brown double monk. The four cover the formal range from black tie to country wear and last, with proper care, fifteen to twenty years each. A man building from less can begin with a single pair of dark brown Oxfords and add from there. The wrong instinct is to own many cheap pairs. The right instinct is to own few good ones.