How to Wear Loafers: Eleven Questions, Answered Plainly

The loafer has a rare advantage: it goes with nearly everything. That's also the trap, because “nearly” hides about a dozen cases where it doesn't, and those are the ones people write to us about.

Here are the eleven questions that come up most, with a straight answer to each. If you're specifically after men's outfits, those are laid out in how to wear men's loafers. This one answers broadly.

1. What do loafers go with, in general?

With anything that leaves the ankle visible or stops just above the shoe. That is the one real constraint: the shoe is low and open at the sides, so it needs air around it.

Everything else follows from that. Trousers that fall onto the foot flatten it. A very long skirt erases it. A well-chosen crew sock, on the other hand, sets it off, and that's the subject of loafers and socks.

2. Which trousers work best?

Straight or slightly tapered, ending at the ankle. That cut flatters every model of the shoe.

Wide trousers can work on one condition: the hem must not rest on the shoe. Have them shortened by an inch and it changes everything. With very slim trousers, take a shoe with some presence — a thicker sole, a squarer toe — or the proportions fall flat. See thick-soled loafers.

3. Can you wear loafers with a dress?

Yes, and it's one of the best combinations there is. A fluid dress and a flat loafer create a contrast that works: the shoe keeps the outfit from turning prim.

Length decides it. Knee or mid-calf is ideal. A dress down to the ankle hides the shoe, and at that point you may as well wear something else. The range is in women's loafers.

4. With jeans?

Yes, as long as the jean is straight and dark. Light, faded, distressed denim pulls the shoe down with it. And roll the hem once rather than letting it drag. Denim loafers are a different idea and work best against a plain trouser, not against more denim.

5. How do you wear loafers in winter?

With a sock you can see and chose deliberately, a thicker sole, and a closed model. A winter loafer isn't a summer loafer in a darker color, it's a different shoe.

What we'd say plainly: don't take a thin pair out in rain or snow. See winter loafers, and if a pair gets soaked anyway, the procedure is in caring for leather loafers.

6. And in summer?

Canvas, light suede, or a perforated leather. With no-show socks, never bare feet: a shoe worn against skin doesn't recover. See summer loafers and fabric loafers.

7. How do you wear patent loafers?

Patent throws light back, so it draws the eye on its own. Everything else you wear stays matte and plain. That's the only rule, and it's enough.

One useful note: patent reads better in the evening and under artificial light than in full sun, where it hardens the silhouette in photographs. The models are in women's patent loafers.

8. How do you wear platform loafers?

A platform adds height without the discomfort of a thin heel. In exchange it asks you to shorten what's above: trousers at the ankle, skirt at the knee. With long trousers over a platform you look like you grew overnight.

Not for you if you're walking cobblestones all day — a thick sole is rigid and doesn't roll through the step. See platform loafers.

9. What goes with heeled loafers?

The square-heeled loafer is the most versatile of the family: it dresses up a jean, goes to the office, and holds a dinner. With straight trousers, a heel of an inch and a half to two inches is the sweet spot.

With a skirt, a square heel lengthens the leg without the severity of a pump. See square-heeled loafers and heeled loafers.

10. What goes with beige loafers?

Beige is the most useful color in the category and the most poorly used. It works with white, brown, khaki and raw denim. It doesn't work against hard black, where it looks like it ended up there by mistake.

The advice that actually helps: go a shade darker than you picture. Very pale beige marks immediately. See beige loafers.

11. And if I only own one pair?

Dark brown, leather, no ornament. It goes everywhere and is wrong nowhere. The two starting points are women's loafers and men's loafers.

The three mistakes we see most

A hem that's too long. The number one error, and the cheapest one to fix.

A size taken too big. With no laces, nothing takes up the slack — if it floats, your heel comes out. If it pinches slightly in leather, that can be worked on, and we explain how in loafers too tight.

Two loud details at once. A tassel shoe plus a chain bag plus a print: each one cancels the next. One thing talks. More on that in how to wear tassel loafers.

For the layer on top of all this, see what jacket goes with loafers, and for which pair to pull out when, when are loafers the right call.