John Lobb is one of the great stories in men's shoes, and it starts far from Mayfair. John Lobb was a Cornish-born bootmaker who went to Australia and made hollow-heeled boots in which miners could stow gold nuggets. He came back and opened a shop on London's Regent Street in 1866. The house opened its first Paris boutique in 1899, and the Paris bespoke atelier is on rue de Mogador in the 9th arrondissement. Hermès acquired it in 1976, ready-to-wear began in 1982, and a Northampton workshop opened in 1994, where each pair goes through a 190-step process. The brand names the Lopez penny loafer and the City II oxford as its best sellers, and they anchor this group. The Lopez comes in suede and in leather, and the Pace and Thorne loafers add penny shapes in suede, nubuck and soft textured leather. The City II is the cap-toe oxford, the Philip II and Taunton are other oxfords, and the William double-buckle monk is the one that sits between a dress shoe and a loafer. If you wear jeans, the polished penny loafer is a good reference, and a hem-first guide to shoes with jeans covers the break at the ankle. Hartland brogues and the Land and Mansell derbies are the other lace-ups.

The second group is the softer half of the shoe wardrobe. The Alder boots appear in leather, in lace-up leather and in suede, and the Lawry Chelsea boot in suede is the easiest one to wear with a suit or with jeans. The Field and Chukka boots are the casual desert styles, and the Peak boot has a rubber sole for weather. The Kingston II and Kingston slippers are for the evening, and a leather-trimmed suede slipper sits near them. The Stream trainers, the Foil boat shoe and the Sommet hiking boot show the range is wider than formal shoes. Here is a pairing test for any loafer or boot: look at your trouser hem in a mirror, and if it breaks over the shoe in a messy fold, take it up before you choose the shoe. What I would skip is wearing the Chelsea or Alder boots under a wide hem that covers the ankle, since the whole point of the shape is lost. Lug-sole shoes in polished leather and boots with a long history are good companions, and the Edgar derby with shoe tree and the Tyne suede loafer round out the group.

My John Lobb pair would be the Lopez in suede with a pair of gray trousers, then the City II oxford when a jacket comes out. He would wear them for years, resoling and polishing along the way, because the house still builds shoes in Northampton the way it has since 1994. For dressing around them, menswear without the stiffness is a place to start.

If you want to keep going, Zegna Loafers and Tailoring is a good next read.