As a natty man-about-town, I don't like to go out without a hat. As I always go out by bike, this limits my hat selection considerably to those that will stay attached to my head in any wind, but not using a chin strap or similar which might risk strangling me if the hat gets caught in low overhanging branches.

My everyday solution to this problem is the flat cap. It's smarter than a cycling cap or baseball cap, and its modest peak doesn't generate enough lift to carry it aloft except in the strongest head winds. It also helps that flat caps have been fashionable for the last few years.

Flat caps really don't go with formalwear, though. If I'm cycling to a job interview or a formal dinner, and I'm wearing a suit or a dress suit, I can't wear a flat cap, a sports cap, or a beanie over that. My hair isn't long enough to support a hat pin of the kind you'd see in a ladies' hat. Is there a style of hat that would satisfy both the practical and sartorial constraints of that situation?

N.B. I don't wear polystyrene hats, so please don't post a comment or answer trying to convince me to wear them.

  • 1
    You could wear an appropriate hat for riding (whatever your selection for on bike) and swap it for your dancing plumage once your ride is ended. N+1 remember!
    – Criggie
    Jan 29 '16 at 12:27
  • 2
    Whatever you feel is appropriate for your funeral. Jan 29 '16 at 12:37
  • This question is hilarious in both form and topic, but unfortunately it's only going to lead to opinion based answers and comments like the "funeral" one. Voting to close as "opinion-based".
    – Gary.Ray
    Jan 29 '16 at 21:16
  • Do you say m'lady a lot?
    – jqning
    Jan 30 '16 at 0:57
  • @Gary.Ray This is a practical, specific, answerable question about a cycling problem I face, and you're closing it because there are trolls on the site? That seems somewhat backward to me.
    – Dan Hulme
    Jan 30 '16 at 10:05

My instant reaction to this is the Deerstalker. Paired with an appropriate cravat this should be able to carry you through the majority of social functions. Tweed being an obvious material for the outdoors.

Depending on how formal you need to go, you might consider a collapsible top hat, which can be changed into on arrival.

Finally, if feeling quirky, a Coke hat would be a viable alternative with the benefit of providing a conversation piece.

  • That coke hat is worth about six times the cost of my entire bike.
    – Criggie
    Jan 29 '16 at 12:30
  • I guess a deerstalker for parties, a bowler for job interviews, and an opera hat for more formal events like weddings would be a good combination. You can never have too many hats.
    – Dan Hulme
    Jan 29 '16 at 13:46
  • Are you mad?! The rear visor on a deerstalker is entirely unsatisfactory for neck angles inherent to cycling. Entirely. A bowler pushed forward at a jaunty angle, on the other hand, might be just the thing. Jan 29 '16 at 21:08

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