A combination of hair loss and a heatwave has renewed my interest in hats.
Unlike my hero Thelonious Monk my engagement with millinery has previously only extended to a beanie in winter and a baseball cap in summer.
What other headgear might I consider?
You need a winter hat and a summer hat and a hat for Spring and Autumn.
Buy the best, even though the price is high they will last a long time if you maintain them (change the ribbon), and a good hat wears well -- a good hat will look good after 15 years, just good in a different way.
Buy from the shop, not online -- they will fit it properly and you need to look at yourself with it to feel right. The size of the brim, the height and the colour really make a huge difference and you can only tell by trying them on. Get them to teach you how to take it on and off so it doesn't get damaged (by the brim, basically) and get a proper box to store it. Lock boxes are fabulous.
Try to buy a hat with a leather sweat band inside, it will wear much better.
Here's my winter hat -- I paid about £100 in around 2010 and it still looks great (I have had the ribbon changed a few times though, and one repair)
Fairbanks trilby - Lock & Co. Hats for Men & Women (lockhatters.com)
Here is my summer hat, mine is in dark brown but I don't see the webpage. I paid about £150 in 2015 or thereabouts. It still looks great, despite having been sat on.
Classic Sisal Trilby – Bates (bates-hats.com)
Here is my Autumn and Spring hat -- I bought it in 2019. The one I have is too big for me (they still don't have medium!) I still wear it, but it's not right. That's how I learned (the hard way) not to buy online.
New York Hat Company Leather Trilby Hat - Black – Village Hats (hatsandcaps.co.uk)