Hats

A baseball cap in navy or black for casual versatility. A quality beanie for all cold-weather situations. A flat cap or newsboy cap bridging casual and smart-casual. These three cover about 90% of hat-wearing occasions. Add a straw hat or bucket hat for summer holidays.

Comfortable without squeezing or leaving marks. Not so loose it blows off or slides over your eyes. Baseball caps should have adjustable straps. Structured hats like fedoras should sit level about 1cm above the ears. If it doesn't feel right in the shop, it won't feel right outside.

A fine-knit beanie in navy, charcoal, or camel works for smart-casual settings. Wear it sitting back on the head rather than pulled down low. Pair with a clean overcoat and quality knitwear. It's a specific look but a good one, the modern equivalent of a stylish winter hat.