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The Damnson Guarantee| Risk-free confidence

Orders ship in 7-10 business days

This hat is a pre-order and is expected to ship 12/15. Your entire order will ship when all items are available. 


Look, we have no way of knowing whether the Rockport would’ve survived Shackleton’s miraculous 400+ day Antarctic expedition, including the Endurance’s mooring in ice, subsequent journey on foot and lifeboat passage. We’d like to think so.

All we can say is that it was designed with such a journey in mind. It’s not the most technically superior headwear, at least by 21st century standards. It isn’t replete with features designed by the brightest engineers of our time or made with space-age materials.

What is does have is character in spades. It will not give up. Put it on your head and you’ll most certainly take on a bit of the strength exhibited by the brave mariners in Shackleton’s company.

At the end of the day, 28 sailors set out on the adventure, and 28 were rescued at the ordeal’s close. The Rockport is the official beanie of that sort of attitude.


The Rockport is made of 100% select acrylic yarn, woven well and woven true. A small, simple foldover tag features the Two Roads logo with contrary signs, signifying a junction and the deliberate decision it requires.