Hawaiian Rose was born on February 2, 1998 in Spanish Town but was raised in Charlemont Housing Scheme in Linstead, St. Catherine. She is an only child for her mother.
Growing up, Hawaiian Rose, whose given birth name is Xavier Woolery discovered at the tender age of six that she had the passion for singing. She would sing at her home In Charlemont and in her community and by the time she was 8 years old she was singing at church; it was there at church someone heard her and encouraged her to start singing in the children's group which she did for 2 years.
At sixteen years old she began constructing her first song which was based on issues she was facing as a teenager, she later discontinued writing the song as it wasn't properly structured in terms of wordings much to her liking. Between the age of 17 and 18 years old after graduating from the Bog Walk High School which is now renamed Edith Bennett High School; she started to be more active in singing, she sung at small concerts, church functions and also in her community.
At nineteen years old she tried again at song writing, she wrote a chorus and by this time she had done performances in Kingston. And at the age of twenty she completed writing her first song which is titled: Dont Waste Time.
She chose Hawaiian Rose as her moniker because after doing some research she found out that the word Hawaiian meant "a female flower" and she paired it with Rose as roses are her favorite flower and putting those two names together she says makes her feel like she was cut from a high quality piece of fabric as she wants people to look up to her.
Hawaiian Rose then moved on to becoming an artiste at 21 years old in the year 2019