Hats hats hats!

Yes, I know this site is all about scarf wrapping, but I have been meaning to make a video about hats for a while, as many of you have requested it.  I don’t wear them often, so therefore I have some questions for YOU!  Fellow hats wearers, what are your hat tips and tricks?  I do have a number of hats that I wear when running out of the house and/or when I want a change from scarves (or extra warmth).  Here are some that I’ve worn recently!

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And now, here are some hat questions for you:
– Is it possible to eyeball hats and know how they will look without uncovering your hair in the store (goes for online as well)?
– What do you wear underneath, if anything?
– How do you make the back of your head/bun part look good (aka not shlumpy)?
– Do you show any hair at the front?  I find that I really don’t like the way that I look when covering all my hair in my hats… so I show a very minimal amount (fine according to the Jewish law I follow).  However, I personally am not comfortable doing this, which is why I tend to avoid hats.  Advice?
– Accessories?
– Any recommendations on where to buy hats?

Also, please share your favourite hats!!