Run a soft tape around your head about a centimetre above the ears and across the middle of the forehead - the widest line, not the highest. Keep it snug enough to stay put and loose enough to slide a fingertip under. That number in centimetres is your size, and it is the only measurement any hatter needs from you.
Felt and wool relax by three or four millimetres in the first month; straw and stiffened cotton do not relax at all. If you land between sizes, take the larger one and pack it with a sizing tape inside the sweatband. Undoing a hat that is half a size too tight is a job for steam and patience, and it rarely comes back the same shape.
A hat that fits sits level, leaves no red line on the forehead after ten minutes, and stays on when you look down at your shoes. If it lifts when you turn your head quickly, it is too big; if it aches behind the ears, it is too small. Nothing about breaking it in changes either verdict.
]]>The difference between a baker boy cap and fancy dress is about two centimetres of forehead. Worn low and straight it reads as a costume; pushed back so the peak sits above the brow line it reads as a hat you own. Angle the peak a few degrees off centre and stop fiddling with it.
A red or camel cap against a grey coat works because the coat is quiet. Two strong colours above the shoulders compete and both lose. If the cap is the colour, keep the scarf plain - and if the scarf is doing the work, take the cap in wool black or charcoal.
The soft eight-panel crown has volume built into it, so hair pushed flat under it fights the shape. Leave the length out at the sides and the silhouette does what it was blocked to do. This is the one hat where a slightly untidy morning helps.
]]>An open weave moves air across the scalp, which is why a straw fedora feels several degrees cooler than a cotton one of the same shape. It also drinks rain and dries misshapen, so it is a hat for the forecast you have already checked. Tightly woven raffia holds a snapped brim; loose panama-style weaves do not.
Wool felt sheds a light shower, takes a centre dent and keeps it, and looks better in year three than year one. The trade is weight and warmth: a felt brim in August is a decision, not an accident. Brush it in the direction of the nap and it stays presentable for a decade.
A washed cotton bucket rolls into a bag, comes out creased, and is fine again within an hour of wearing. It is the only one of the three you can put through a wash, which over a summer of sun cream and salt water matters more than the silhouette does.
]]>A brim carries the weight of the crown badly. Left face-down on a table for a week it flattens at the front and no amount of steam brings the curve fully back. Store the hat upside down on its crown, or on a hook that takes the sweatband rather than the felt.
A soft brush, moving anticlockwise with the nap, takes off almost everything. For a mark that will not lift, a barely damp cloth and a little patience beat any cleaning product sold for the purpose. Sweatband stains come out with cold water and a toothbrush, and only cold - warm water sets them.
Reshape it while it is still wet, then let it dry away from radiators and sunlight, standing on its crown. Heat is what ruins a wet hat, not water. A shower's worth of steam afterwards will lift the nap again and take out the last of the creases.
]]>A flat brim draws a hard horizontal line and squares off a round face; a pre-curved brim softens a long one. That is most of the choice, and it is worth trying both in front of a mirror before worrying about the colour or the badge on the front.
A structured six-panel keeps its height whatever your hair is doing, which is useful on a bad morning and stubborn on a good one. An unstructured dad cap collapses to the head and disappears into an outfit. Neither is better; one is a garment and the other is a habit.
Full shade all the way round, packable, washable, and completely indifferent to how it looks by the time you get home. If you own one hat for travelling, this is it - and the plain washed cotton versions age far better than anything printed.
]]>Most autumn hats fight with a raised collar or a scarf. A beret has no brim to catch and no crown height to crush, so it goes under a hood and comes back out unbothered. That is a practical reason dressed up as a fashion one, and it is the real reason they keep returning.
Pull the fullness to one side and let the opposite edge sit close to the head. Straight on and flat it reads as a uniform; slightly asymmetric it reads as yours. Wool felt holds the position on its own, and a soft knit needs a pin.
Leather and coated cotton take the rain and read sharp against a puffer. Camel or charcoal wool is the quieter one, and it is the version that still works over a tailored coat in February. If you buy one, buy the wool.
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