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I don't own any bowler/derby hats but wouldn't it be hard to place pinches in the hard shell of most bowlers?Welcome to the FL Granville. Wonderful photos of Irish Republicans from way back then. Interesting to see them from a hat perspective.
Firstly, who knows how the police, press, or others would term a hat back then. Fedora / Trilby could well be interchangeable. However, I think it safe to say, a Fedora has a wider brim than a Trilby.
Secondly, I agree with Robert @belfastboy that Michael Collins appears to be wearing a Lord's Hat style of Homburg.
Thirdly, I doubt very much that De Valera would have put pinches in his Bowler unless it was to cock a snoop at the Brits. In which case it could be likely.