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I have both -- an All-Star helmet and a WV mask. I wear both about equally deciding which to wear depending on my mood.
I work baseball only and I would NEVER wear a hat under the helmet. I work in an area without "associations" and assign all my games directly so I have a hard time believing someone could possibly be so anal about uniforms. I've worked HS, College and summer baseball with the helmet -- it's simply not made to be used with a hat, although that's why I don't use the helmet 100% -- sometimes I'd rather go with the hat/mask cause the helmet is quite a bit hotter.
I wear an 8-stitch hat behind the plate. I hate the combo hats on the bases and I'd rather not have to order two different length bills, so I got used to taking the mask off over an 8-stitch. Out and THEN up and you can get a mask off over any hat. Just remember -- don't duck your head down when removing your mask cause you could miss something while your head is pointed down.
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