When the delivery was in Barrrney's Barrr the script could have worn the shoes, to complete the quest faster, but did not.
What it did was, seemingly, ignore the fact the that delivery location was already open, proceeded to get the Pirate Fledges ,and then go back to the Barrr to complete the delivery. Only after getting the fledges did the script equip the shoes.
When the delivery was in Barrrney's Barrr the script could have worn the shoes, to complete the quest faster, but did not.
What it did was, seemingly, ignore the fact the that delivery location was already open, proceeded to get the Pirate Fledges ,and then go back to the Barrr to complete the delivery. Only after getting the fledges did the script equip the shoes.