I have faithfully worn some kind of baseball cap for 20+ years and I simply love them: a nice low-profile adjustable cap with a curved brim. You can wear them straight, backward, cocked up or pulled low (wearing it sideways makes you look like an idiot). They require no special care and are generally cheap and replaceable.
But they don't look good with a suit or anything other than extremely casual wear.
So, I thought I might try a Trilby. How about a classic jaquard plaid gray trilby to go with my charcoal wool coat? This is also sometimes called a stingy fedora because it has a shorter brim.
[AoM] Yet hats are due for a full resurgence. Hats are both functional and stylish. They can cover a bad hair day, keep your head warm, and shade your eyes from the sun. They can also be worn to cover a receding hairline, which interestingly enough is why Frank Sinatra, an iconic hat wearer, start wearing one in the first place. They give you touch of class and sophistication, impart personality, and add an interesting and unique accent to your outfits. And hats are a sure-fire way to boost your confidence. A cool hat can quickly become your signature piece and give you extra swagger.
Of course men today still wear hats, but they are most often confined to ratty baseball caps, hippie beanie caps, or the thankfully almost extinct trucker hat. There is nothing wrong with these kinds of headpieces per se, but there are other hat options out there. So mix up your lids with various options:
[AoM] You’ve got a chin like: Paul Dano
Pick a hat that will draw attention upwards, away from the chin.
Crown: Low height
Hat Band: Narrow
Brim: Flat, or very shallow snap
Tilt: Level, with significant side tilt.
Recommended Hat: Porkpie, Trilby, Fedora with short crown and brim