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Yeah, I know your troubles. I tried the pro team on last year and it's super tight on the ears of you have a big head... Will recommend trying it on first. I ended up buying the merino hat instead and that served me brilliantly. It looks a little naff under a helmet with the lack of a peak but it covered the ears reasonably well and is super comfortable. Wore it hiking as well...
Ha, I didn't even know that. Every other winter hat I've seen/owned, including the previous Rapha ones have the ear flat too far back and coming down in a curve with the lowest point on the back of the neck. This means you can either have you ears covered or have the peak down the stop rain, not both at once, and if you look up too much then it gets pushed off your head slightly.