Derbies, oxfords and loafers: formal shoes explained

Oxfords, derbies and loafers are the three leather shoes every wardrobe is built on. Oxfords have closed lacing and are the most formal, right for funerals, interviews and black tie. Derbies have open lacing, fit more feet and work from chinos to suits. Loafers have no laces and are the smart casual choice for heat and weekends.

How do I tell an oxford from a derby?

Look at where the laces sit. On an oxford, the two pieces holding the eyelets are stitched underneath the front of the shoe, so they close neatly into a V. On a derby, those pieces are stitched on top, like flaps, so the lacing opens wider. The difference looks small but changes how formal the shoe feels (Oxford shoe on Wikipedia).

When should I wear oxfords?

Funerals, job interviews, formal weddings, black tie and serious business meetings. A plain-toe or cap-toe black oxford is the most formal everyday shoe. Brown oxfords suit navy and grey suits for daytime.

When should I wear derbies?

Almost anywhere smart. Dark brown derbies work with navy and grey suits, chinos and even dark jeans, which makes them the most useful leather shoe for a working week. They're also easier for men with high insteps or wide feet.

When should I wear loafers?

When an outfit needs to be smart but relaxed, and especially in the heat. Loafers suit chinos, linen suits, tailored shorts and smart casual events. Penny loafers are the classic; suede loafers are softer.

What are brogues?

Brogueing is the decorative punched holes along the seams. Any of these shoes can have it. More brogueing makes a shoe more casual: a full brogue (wingtip) oxford is less formal than a plain oxford.

What about monk straps and boots?

Monk straps close with buckles and sit between oxfords and derbies in formality. Chukka and Chelsea boots are smart casual. See the only shoe guide a man needs.

Which should I buy first?

Dark brown derbies, then black oxfords, then brown loafers. See the 5 types of shoes every man should own.

How do I care for leather shoes?

Rotate pairs, use cedar shoe trees, polish every few weeks, and resole rather than replace. See how to care for a suit for the matching wardrobe routine.

Questions

Can I wear derbies to a funeral?

Black derbies are acceptable at most funerals; black oxfords are the most correct.

Can I wear loafers with a suit?

Yes, with navy, grey and linen suits for daytime and smart events. Not for funerals or formal interviews.

What socks go with these shoes?

See what socks to wear with sneakers, loafers and dress shoes.