Fedoras

Wider brims balance round faces; narrower brims suit longer faces. Taller crowns add height for wider faces; lower crowns suit taller foreheads. As a rule, your brim shouldn't be wider than your shoulders or narrower than your cheekbones.

Wool felt in charcoal or grey is the single most versatile fedora it works from early fall through late spring with everything from jeans to sport coats. For year-round coverage, add a straw or Panama for summer.

Fedoras have medium to wide brims that can snap up or down. Trilbies have shorter, upturned brims and are more casual. Homburgs have a single center crease and a stiff, curled brim they're the most formal of the three.

For a quality fedora that holds its shape and looks sharp, expect $60-$150 for wool felt, $100-$300 for fur felt, and $80-$250 for genuine Panama. Below those ranges, construction and materials tend to suffer noticeably.

Yes match the formality of the hat to your outfit. A straw fedora with a t-shirt and jeans is perfectly casual. A fur felt fedora with a blazer is smart-casual. Problems arise when the hat is dramatically more formal than the rest of your clothes.