The One Direction star got an impressive naval galleon inked on his left arm at Shamrock Tattoo Parlour in Los Angeles, while his new girlfriend Taylor Swift and his bandmates looked on for moral support.
"Taylor made sure she was close by to hold Harry's hand through the procedure, with the singer chatting to a female pal as her boy band beau went under the needle," MailOnline reports.
Despite a rather sore-looking bicep, the 18-year-old singer grinned as he underwent the painful procedure at the parlour, which is a favourite with stars including soccer player David Beckham, and later posed for pictures with country singer Taylor.
'Really personal to him'
The Little Things hitmaker is addicted to body art and is keen to add to his already impressive collection of tattoos. His last tattoo - which was also etched at Shamrock last month - was a giant pair of birds on his chest.
"Last time I spoke to Harry he said he is going to hold off on the sleeve for now but will be getting new bits soon," celebrity tattooist Kevin Paul commented.
"They're really personal to him - the reasons he had them done and stuff, so he doesn't really want to announce what they are. One was something from his childhood, and another one was something really important in his life."