In order to unlock this trophy you must purchase a Grove Street tattoo. The tattoo parlor next to the barber shop and pizza place will become accessible after the second mission in the game titled ‘Ryder’. Now you can’t just buy any tattoo, especially if you want this early in the game as you have limited funds. The tattoo you would want to purchase in this case is the 70 dollar one that can be put on your stomach. As soon as you purchase the tattoo and the artist does his thing, the trophy unlocks.
I hope this solution helped! Leave a comment letting me know if there is any room for improvement! Thanks.