First, a definition#
A loafer is a dress shoe with no lacing. That’s it. If it has laces it isn’t a loafer, whatever the shop calls it.
Most good ones are leather. Suede is leather too, just finished to show more texture — plenty of men avoid it fearing damage, and it is more delicate, but treated and brushed it’s one of the better things you can own.
Why the penny one first#
Designed in the 1930s, everywhere through the fifties and sixties, and still completely current. College students adopted them and were still wearing them at sixty, which is about as good a durability test as a design gets.
There’s a decent argument for spending on a good pair, and it’s the Lindy effect: the longer something has already survived, the longer it’s likely to keep surviving. A hundred years in, the penny loafer is a safe place to put money.
One buying tip that saves a lot of grief — match the colour to the shoes you already own. If your dress shoes are all black, buy black. If you wear browns, pick a similar brown. You’re adding a style, not a whole new palette, so it mixes with what’s already in the wardrobe rather than needing its own outfits.
The ladder, casual to dressy#
- Moccasins — the most casual slip-on there is. Originating with the Native peoples of North America, and identifiable by the stitching running around the outside of the top. Classic ones had no real sole, just a leather covering that got replaced while the top went on forever. Made for denim, arguably for shorts. Never for a suit.
- Driving shoes — a moccasin variant with rubber studs instead of a full sole. Genuinely designed for driving, where you want pedal feel and grip. They are not built for walking around in and they will not survive being used that way.
- Belgian loafers — casual, often suede, sometimes in genuinely bold colours. Versatile and very comfortable in a good pair.
- Horsebit loafers — around 1953, made famous by Gucci, Italian-only at first and a serious trend by the 1980s. The metal bit does nothing whatsoever, which is exactly why it takes a bit of nerve.
- Penny loafers — the middle of the ladder and the safest place to stand.
- Tassel loafers — appeared just after the Second World War in Europe. The dressiest of the lot, rarely made in light colours, and the hardest to wear with denim. Possible with dark jeans and a mid-brown pair, better under a sports jacket, and not a first purchase.
Wearing them with denim#
Loafers are technically dress shoes, so distressed denim is oil and water. Unless you’re in a band, skip that pairing entirely.
- Slim and straight cuts are the safe bets.
- Relaxed works, especially on bigger men, as long as the leg opening isn’t wide.
- Skin-tight and baggy both fail, in opposite directions.
Black is the most formal shoe colour there is, so for denim go lighter than black. It can be done, it’s just the hard version.
For summer specifically#
Look for unlined suede and a lower vamp — less of the foot covered means noticeably cooler, and genuinely more comfortable than a sneaker in heat.
The outfit that goes with it: no-show socks, cream chinos, and a chambray shirt with the sleeves rolled. Chambray is a very lightweight denim, usually a shade of blue. Put those three together and you look like you have somewhere better to be.
The one nobody owns#
A shoe billed as the one most men are missing turns out to be the double monk strap.
It’s been in fashion for over a decade, some people consider it overplayed, and most men have still never heard of it. Two buckles give it a bit of flash, it slips on and off in a second — useful at an airport — and it works with a suit, with a jacket and trousers, and dressed down with chinos and a linen shirt.
A few small things to try:
- Check what colour your existing shoes are before buying loafers.
- Try unlined suede once. It’s a different shoe in July.
- Look at your jeans’ leg opening before blaming the shoe.
- If you already own penny loafers, the monk strap is the next one.
