How is this hat mailed, any possibility of it being crushed?

Mine was mailed in a box. Yours should be safe.

What material is the mesh made out of?

Ummmm not sure a but it’s comfy and flexible. A little better than the usual trucker hat mesh on some hats.

in the first picture there looks like a rip, it is intentional

It is not a rip. I bought it for a friend (he rides a HD dyna wide glide) and he loved the details of the cap, and it’s HD official product, so, no worries.

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