The Captains Hat
“ | My wonderful hat... It's gone... | ” |
— Josh, crying after he briefly lost his hat |

Josh's Captains hat has become a staple in the lore, and an essential part of his outfit. Josh is usually found wearing his captains hat, except when he is traveling to avoid it being stolen or lost. During the Michael Quinn Era, Josh's hat was stolen multiple times, leading to him claiming that the hat was microchipped and had a tracker sewed into the fabric.
Lately, due to these repeated theft incidents, Joshua only wears the hat in New York when recording his TikTok as he claims he is only the "Captain of New York" or on sea. Josh has also worn other hats before such as a cowboy hat. Josh also allegedly keeps backup hats in his bag in case it gets stolen. He has refused similar captain's hats from other people for not being authentic to his. A variant of the hat is sold on his online store.