Style · Shoes

Five Pairs of Shoes, Twenty Years

· 7 min read

A Goodyear-welted shoe rested every other day and resoled twice lasts two decades. Five pairs cover a life. Here is which five and how to keep them.

Most men own fifteen pairs of shoes and wear three of them. The three wear out, get replaced with something similar, and the cycle repeats every two years for a lifetime. Five good pairs, rotated and resoled, break the cycle. The initial outlay is higher; the cost per wear over twenty years is a fraction.

The five

  • Black cap-toe oxford. The most formal shoe you will own. Suits, funerals, interviews, black tie in a pinch. Plain, closed lacing, leather sole.
  • Dark brown derby or split-toe. Open lacing, slightly heavier, the shoe for the navy suit on a normal day and for grey flannels with a jacket. A Dainite rubber sole makes it a winter shoe.
  • Brown suede loafer. Penny or tassel. Chinos, jeans, a linen suit in summer, no socks in August. The shoe you will wear most.
  • A boot. A chukka in suede or a plain-toe boot in brown calf. Autumn and winter, weekends, travel. With a commando sole it replaces the derby from November to March.
  • A white leather sneaker. Plain, minimal branding, kept clean. For everything that is not tailoring.
A shoe worn every day dies in two years. The same shoe worn every third day, on trees, lasts twenty. Rotation is not indulgence, it is arithmetic.

Why welted

A Goodyear-welted shoe has its sole stitched to a strip of leather, the welt, which is stitched to the upper. When the sole wears through, a cobbler stitches on a new one without touching the upper. Cemented shoes, the ones glued together, cannot be resoled properly. The welted shoe costs €350 to €700; the resole costs €120 every four or five years. Over twenty years the welted shoe is the cheaper one.

Care that takes five minutes

Cedar shoe trees in every pair, inserted while the shoe is still warm. A horsehair brush after every wear. Cream polish once a month, wax on the toe cap if you like a shine. Suede gets a brush and a protective spray twice a year. Wet shoes dry slowly at room temperature, never on a radiator. That is the whole regime.

Where to buy

Northampton in England, the Marche in Italy, Mallorca in Spain and a handful of makers in Portugal, Hungary and Germany produce most of the good welted shoes in Europe. The price band from €350 to €500 buys excellent construction; above that you pay for hand-finishing and leather selection, which are pleasures rather than necessities. Buy the first pair in a shop where someone measures your foot. After that you know your size in that last and can buy online.

Questions we get asked

Leather or rubber soles?

Leather for the oxford, rubber for everything you wear in the rain. A leather sole with a thin rubber topy added by the cobbler is the compromise most men settle on.

How do I break them in?

Wear them at home for an hour a day for a week, with the socks you will wear them with. A good welted shoe is stiff for a fortnight and then perfect for years.

What about black shoes with a navy suit?

Correct and slightly formal. Dark brown is more modern and works with everything except the darkest charcoal and black tie.