Old Money Loafers

Old money loafers earn their place by being the shoe you can put on without thinking. No laces, no ceremony, and enough restraint to pass in most rooms. Suede in navy, chocolate, olive and stone. Penny straps for the plainest version, tassels for a little more, a buckle when the occasion asks. Worn until the leather remembers the shape of the foot, then worn some more.

A slip on lives or dies on how it holds the heel, which is the first thing to judge in any pair of old money loafers. Everything else follows: the vamp height decides how much foot shows, the sole decides where you can wear them, and the nap decides how often you will be brushing them.

Penny, tassel and buckle: the three families

Old money loafers come in three families. The penny carries a plain saddle strap with a slot cut into it and is the most versatile. The tassel adds a corded trim and a touch of the 1960s, which makes it slightly dressier and considerably more distinctive. A buckle sits closer to a monk strap in feel. Tassel loafers read best with flannel, while a navy suede penny handles almost everything.

Suede or calf, and where old money loafers belong

Suede is softer underfoot, reads relaxed and suits daylight, linen and warm weather. Polished calf is smarter, takes a shine and works under tailoring where a lace up would otherwise be expected. Neither belongs at a black tie event. Match the register of the trouser: suede with the softer cuts in our trousers, calf with anything cut for a jacket.

Fit, socks and the break-in period

A loafer should feel snug across the instep on the first wearing, since it has no laces and will relax roughly half a size. If the heel slips more than a few millimetres, size down. Invisible socks in summer, fine wool in winter, bare feet only in genuine heat. For the lace up equivalents, the range continues in formal shoes, and beige suede is the easiest starting point.

Loafer questions, answered

Are loafers smart enough for an office?

A polished calf penny or tassel in black or dark brown works in most business casual settings and with a soft suit. In a formal City environment an oxford still outranks it. Suede loafers are a step below and better suited to Fridays and summer.

How should a loafer fit when new?

Snug across the instep with the heel held firmly and only a few millimetres of movement when you walk. The leather will give roughly half a size as it warms and flexes. A pair that feels comfortable straight out of the box will be loose within a month.

What is the difference between a penny and a tassel loafer?

The penny has a flat leather saddle across the vamp with a small slot cut in it, and the tassel has a corded lace ending in two decorative tassels. The penny is plainer and more versatile; the tassel is slightly dressier and more distinctive. Both sit at the same level of formality in practice.

Can you wear loafers with a suit?

With a soft, unstructured suit in flannel or linen, yes, particularly a plain calf penny in dark brown. With a formal business suit or anything ceremonial, a lace up is still the correct answer. The heavier and sharper the tailoring, the less a slip on belongs.

How do you look after suede loafers?

Brush the nap with a crepe or brass brush every few wearings to lift dirt before it settles. Spray a protector before the first outing and every couple of months after. Never apply cream polish, which flattens the nap.

What trousers work best with loafers?

Anything with a clean hem that just touches the shoe, so the vamp stays visible. Flannel, chinos and linen all work; a heavy break drowns the shoe and ruins the line. A slight taper at the ankle keeps the proportions right.