How to Pick a Hat for Your Face

Everyone has had the experience of putting on a hat that looks great on a friend and terrible on them. It isn't taste and it isn't luck. It's geometry, and once you know the rules you stop buying hats that end up in a drawer.

Rule one: contrast the shape

The most reliable principle in headwear. Pick a hat that contrasts with your face shape rather than repeating it.

• Round face — you want structure and angles. A flat brim, a higher crown, a five-panel. Avoid soft round bucket shapes, which double down on what's already there.
• Long or narrow face — you want width. A curved brim, a lower crown, a bucket. Avoid tall structured crowns, which lengthen further.
• Square or angular face — softer shapes balance it. Curved brims, unstructured caps, bucket hats all work.
• Oval face — most things suit you. Enjoy it.

Rule two: match the brim to your shoulders

Less obvious and it's what makes a hat look off when you can't say why. The brim should be roughly in proportion to the width of your shoulders and jaw.

A wide flat brim on a slight frame looks like the hat is wearing the person. A small brim on a broad, tall frame looks undersized and slightly comic.

Broad shoulders can carry a bucket and a wide flat brim. Slighter builds look better in a curved brim and a lower profile.

Rule three: crown height and hair

Crown height is the bit nobody checks and it's frequently the actual problem.

A high structured crown adds an inch or two of visual height. Good if you're short or have a rounder face. Overwhelming if you're already tall and narrow.

A low unstructured crown sits close to the head and disappears. Flattering on most people and the safest choice if you're unsure.

And be honest about hair. A hat that sat perfectly when you had more of it will sit differently now — usually lower, and often it needs a size down. This catches a lot of people out, and they conclude the style stopped suiting them when actually the fit changed.

Wear it properly

Two-thirds of hats that don't suit people are simply worn wrong.

• The brim should sit just above your eyebrows, roughly level. Perched back looks unfinished; pulled low looks like you're hiding.
• It should be level, not tilted, unless you're very confident.
• It should be snug, not tight. A visible red band on your forehead after a round means it's a size too small — which also gives you a headache by the twelfth.