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I remember that Photocrapper post but just giving specific shipping instructions can't hurt and may possibly help. My second shipper never shipped a hat before and giving her specifics made me feel more comfortable.
Y'know, it can't hurt to let them know your expectations.
Then there's this guy, who's auction for a Hommie ends soon, "Unless I hear otherwise, I will send this in a flat rate priority box, which is about 5 inches tall on the inside. You will have to push the crown back up and into shape, but it will keep the shipping costs down."
At least he/she's honest your hat will be crushed!
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