I also look good in a hat.  My wife looks good in sunglasses, but I do not.  I think that certain faces are made for these things.

I have not put on a fedora in fifteen years, but I am a partisan of the Panama in summer.  I think it is a lot easier to wear without looking costumey.

Posted this in FNB's "A Place to Hang My Hat" discussion last Spring, hence the then current references to straw lids.  To bring it up to date, today I'm wearing a dark brown fur felt trilby (unlined, half inch brown ribbon, center crease, sharp pinch) and some other apparel not relevant to this thread:

Growing up in the 1950s, with a grandfather and father in men’s retail, I simply assumed that when I became a “man” I would wear a hat.  Then, in 1961 when I was in my mid teens, JFK gave his inaugural address sans his (top) hat and that date is commonly marked as the end of hats as an essential element of a properly dressed man’s attire.  Consequently, though following my family’s motto, “Think Yiddish, dress British,” in all matters sartorial, I went about bare headed–especially bare after I lost it all on top–in all seasons and manner of weather.  Then, one day about twenty years ago, I tried on a Donegal newsboy cap in an Irish store and have scarcely been uncovered outdoors since.  My wife is of a younger generation, but nonetheless loves me in all kinds of hats except, ironically, newsboys.

I wear fur felt fedoras, trilbies, stingy brims, porkpies, etc. in fall and winter and all manner of straws in spring and summer.  Indeed, I virtually always don some sort of hat when leaving home, no matter my activity or my attire’s formality or lack thereof.  For example, last weekend I helped a friend move heavy furniture around in her dusty basement and wore old snap brim panama with black ribbon atop my black tee shirt, well-worn carpenter jeans (held up with red galluses), deerskin work gloves, and steel toed work boots.  I had not thought about it until another old timer there said I reminded him of pictures of construction workers from the 1920s-30s; but everything worked perfectly for the task, particularly the hat which kept the dust off my head and out of my eyes and warned me whenever I came too close to overhanging pipes, ducts, and beams.

Today is work but no court, depositions, or the like, so casual dress.  I chose a dark tan coconut straw Borsalino with pinched, tapered crown, wide turn down brim, and gold ribbon to wear with a black plain weave silk camp shirt printed with small gray and gold geometric pattern, mid gray tropical worsted trousers (pleated, cuffed), brown alligator belt, and walnut split toe derbies (and black/gray mini check lisle socks, for the sock discussion).  Tomorrow, who knows; but I’ll be wearing a hat.

My work and social life put me in contact with a wide range of adults of all ages, races, and educational and economic strata; and I am often complimented by both women and men on my attire, only occasionally with specific mention of my hat.  In other words, the hats do not stand out on their own.  My favorite recent experience is with a bus driver, a middle aged African American man, who has taken to calling me “Old School.”  The rare negative comment is usually from the sort of person a compliment from whom would likely cause me great sartorial distress.

I do not urge anyone else to wear hats.  I, however, am quite content that my head is never too cold, too hot, too wet, or to wind-blown (I still have some hair).  Directly on topic, my hats reside carefully nested on shelves in a cabinet that also is home to my sweaters.  Caps, even a few baseball (sized and closed back, naturally), are on hooks in various closets.

This hat size thing is new to me.
Which way 'round does it work?
Larger in the U.S., I guess?

M.

Good to know.
I'm in the market for a new Tweed bucket & am tempted by the good value presented by LL Bean.
I shall ponder...