Socks With Loafers, Sneakers, Juttis and Kolhapuris: The Rulebook

Most sock mistakes aren't about the sock. They're about the shoe. A brilliant pair of crew socks looks wrong with low trainers, and a perfect sneaker sock vanishes uselessly inside a boot. So here's the rulebook, shoe by shoe, including a few that most sock guides forget exist.

The rule behind all the rules

The higher the shoe's collar, the longer the sock. Shoes that cover the ankle want crew socks. Shoes that sit low want short socks or none. Everything below is that one idea, applied.

Shoe by shoe

Shoe	Sock	The rule
Oxfords, brogues, derbies	Crew	Always a full sock. These are the best shoes for a statement pair, because they're plain enough to let it shine.
Loafers	Crew, or none	Two schools. A bold crew sock with loafers is classic and fun; bare ankles (or a hidden no-show liner) is the summer look. Ankle socks in loafers is the one that doesn't work.
Low sneakers and trainers	Sneaker or ankle	Sneaker socks for the clean, sockless look; ankle socks if you want a flash of colour above the shoe.
High-tops and basketball shoes	Crew	The sock should rise above the collar, or it slides down and bunches.
Running and gym shoes	Sneaker	Low, snug and out of the way.
Canvas shoes	Ankle or sneaker	Ankle for a peek of colour, sneaker for none.
Chelsea and ankle boots	Crew	Anything shorter rubs where the boot's collar sits.
Juttis and mojaris	Usually none	Traditionally worn barefoot. If a new pair is biting, a thin sneaker sock in a skin or matching colour saves your heels while you break them in.
Kolhapuris	Usually none	An open sandal made for bare feet. Socks with kolhapuris is a deliberate fashion choice, best saved for cold days and a confident mood.
Sandals and floaters	Your call	Socks with sandals is the most argued-about look in footwear. If you do it, commit: crew length, a bold pair, said with your chest.

Blue Q I'm An Adventure Man men's crew socks — I'm An Adventure Man: a crew sock built for boots and brogues

Loafers deserve their own section

Loafers sit right in the middle of the sock debate. Here's how to choose:

Formal or cooler days: a crew sock, ideally with a dark base and one bright colour. With cuffed trousers or a cropped hem, the sock becomes the feature.
Hot days and casual outfits: bare ankles, with a no-show liner if you want to protect the shoe from sweat.
Never: an ankle sock that peeks a centimetre above the loafer's collar. It looks like you started one look and abandoned it.

Sneakers: how much sock should show?

It depends on the trouser. With full-length jeans, nobody sees, so wear what's comfortable. With shorts or cropped trousers, choose between almost nothing (sneaker socks) and properly visible (crew socks, the slightly retro look). The halfway option, a sock that barely clears the shoe, tends to look accidental.

Ethnic wear: juttis, mojaris and kolhapuris

These shoes were made for bare feet, and they look best that way. Two honest exceptions:

Breaking in a new pair. Stiff leather juttis can rub. A thin, low sneaker sock in a neutral colour protects your heel for the first few wears.
Winter weddings. Cold floors and long evenings are reason enough. If you wear socks with ethnic shoes, go for a closed jutti and keep the sock short and quiet, so the embroidery stays the star.

With a sherwani and closed formal shoes, the formal rules apply: crew length, and this is your chance for a secret statement pair.

Matching colour, in one rule

Match your sock to your trousers for a long, clean line, or match it to nothing at all and echo one colour from your shirt instead, so the clash looks deliberate. Matching your sock to your shoe is the least interesting option.