I'm a big fan of baseball caps in traditional fabrics like tweed. This herringbone tweed cap from The Hill-Side has a buttery soft brim and is fairly unstructured, which, like your jackets, can be a good thing to look for in your caps. I remember back in the day we used to rip out all the lining and canvasing in our baseball hats to get them to break in extra comfortable. We also used to shove our brims into coffee mugs to get them aggressively curved too. Talk about a history of baseball hat violence. We really spent almost as much time breaking in our hats as we did wearing them. No wonder I write about $70 hats now.