Not all hats are created equal

Start here.

[ ¶ ]

Worst: A baseball cap

The long visor of a baseball is really wonderful for keeping the sun out of my eyes, but it does such a good job of getting in the way of the bayit (box) of my shel rosh (head tefillin) that I have to turn the hat backward.

[ ¶ ]

Better: A dress hat with a turn-down brim

My white dress hat is delightful for dancing at a simchah/happy occasion, but the bent-down part of the brim actually gets caught on the front edge of the bayit! I have to be sure that the hat is set farther back on my head.

[ ¶ ]

Best: My black dress hat

The brim’s not too wide and isn’t bent down at the edge. Perfect, says Goldilocks. :)

[ ¶ ]

[ ¶ ]

Speaking of design, see also "Too Jewish," which you might find good for a chuckle.

[ ¶ ]

Update: Here's my current hat collection.