I'm probably writing about hats a bit too often since many if not most men, even suit-wearing men and particularly men under 30, don't wear them (baseball caps do not count). Jack Kennedy and the automobile get most of the blame, but that's not the point. There are occasions when wearing a hat is smart (intelligent), as well as smart (good looking). By the time a man begins to lose his hair he should own a few.
There are several styles of hat, in two basic constructions for spring and fall. That's straw in the summer (May 15 to September 15 in temperate Northern hemisphere climates) for protection from the sun, and felt, preferably beaver felt, the rest of the year for protection from the cold.
Formality in headwear descends from top hats to homburgs to bowlers to fedoras to trilbys to more casual hats like the pork pie and finally caps. A man chooses the right hat for the day based on the rest of his clothes.
Top hats of the right sort aren't made any longer and high quality used ones cost more than many automobiles. But that's OK unless you are going to be attending a full dress ball or Royal Ascot. The rest of the time, a black felt Homburg does nicely with black tie and dark city suits.
For less formal occasions, dark gray or navy fedoras look very elegant with suits as do brown trilbys on the weekend and tweed caps to complement - but not match - your tweeds.
In summer, the Panama hat comes into its own as does the straw boater, seen at Henley Regatta and in the evening, and linen caps for casual wear.
That amounts to half a dozen hats and as many caps:
-navy and gray Fedoras
-Two Panamas (alternating them gives the sweat bands time to dry out)
-Three tweed caps
-Three linen caps in cream, buff and light blue
And that's all I'll have to say about hats for a while.