The edit ยท Updated 20 October 2026

The best loafers, from classic to chunky

Loafers work with jeans, trousers and skirts, and they are easier to walk in than most flats. We compared four styles at different prices.

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1
The original
G.H. Bass

Weejuns Whitney Penny Loafer

Typical price: around $150

The penny loafer that started it all, in polished leather. Firm at first, then softens with wear.

2
Most comfortable
Sam Edelman

Loraine Loafer

Typical price: around $150

A soft leather loafer with a horsebit detail and a padded footbed. Comfortable from the first wear.

3
Best chunky style
Dr. Martens

Adrian Tassel Loafer

Typical price: around $170

Tassel loafer on Dr. Martens' air-cushioned sole. Sturdy, grippy and good in the rain.

4
The luxury classic
Gucci

Horsebit 1953 Loafer

Typical price: around $1,000

The original horsebit loafer, with a soft collapsible heel. An investment pair that has stayed in style for decades.

How to choose

Expect a break-in

Leather loafers usually feel snug at first and stretch slightly. Avoid pairs that pinch across the widest part of the foot.

Pick the sole

Leather soles look elegant but slip in the wet. Rubber or lug soles suit daily commuting.

Mind the heel

Loafers can slip at the heel. A thin heel grip fixes this if you are between sizes.

Prices change often and vary by retailer, size and colour. Always check the final price on the retailer's site. Comparing it is exactly what The Fitting Room is being built to do for you.

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