The overriding concern when wearing a hat is that you can appear too try-hard, effete or pretentious. To avoid this, and prevent your accessories fighting for attention, go for a tonal palette and if it feels like you’re going over the top, keep things minimal. Treat your hat like your tailoring, and respect all the usual rules when it comes to fit, proportion and personal taste. The secret is in simplicity, so here we look to some of the most stylish hat-headed gentlemen whose distinguished style is classic and timeless.

1. The Fedora

A particularly nostalgic style reminiscent of a glamorous era gone by, the more formal fedora’s sweeping brim and tall crown evoke Bogart inThe Big Sleepand Delon inLe Samouraï.Both wear theirs with a trench coat for clandestine cool, and the extra length in their outerwear helps balance the proportions of a wider-brimmed hat, but Morgan Freeman ups the ante in dramatic, deep purple eveningwear and a black fedora inNow You See Me. The lesson here is to keep the colour of your fedora neutral so you can get as much wear out of it as possible, as they only get better with use.