"I had tattoos on my arms and leg and when I went for interviews I would wear long sleeves because I knew otherwise, I definitely wouldn't have got the job, or even be given a chance," Ms Winzer said.
She managed to secure a role at a company but quickly realised things could have turned out differently had she not "covered up" after seeing her boss' reaction to her coloured hair.
"She would always give me s***t with how I looked," Ms Winzer said. "She would make me feel uncomfortable or weird, to the point where when I dyed my hair back to brown, she stood up and clapped as I walked into the office."
"She definitely wouldn't have given me the job if she saw my tattoos. I was a really hard worker, my commitment to my job never changed, I was still the same person, doing the same amount of work.
"It bothered me a lot at the time and still does, especially talking about it now."
Originally from the South Coast of NSW, Ms Winzer said when she first moved to Sydney about six years ago people would often walk past her and just stare.
"It's definitely much better to when I first got tattoos. People's reactions are a lot less β it's not like what it used to be and I think that's because people are starting to realise it's not just for rough people in jail."
After completing her tattoo apprenticeship, she left her office job and opened her own studio, which is now run by her friend.
"I didn't know whether there was a market for the kind of art work I was doing until I began to upload my designs on my blog," she told news.com.au.
People were immediately drawn to her designs β which often feature pop culture icons, glitter, florals and galaxies β inundating her with requests.
"I remember Miley saying to me once she will never get colour off anyone but me. 'No one gets colour like you', she told me."
Ms Winzer clearly remembers sneaking Miley into her workshop in the Sydney suburb of Alexandria in the early hours of the morning about five years ago.
"Her assistant wanted to get a tattoo while they were in Australia for her concert and so my Instagram followers started to tag him in my work β I guess it is because at the time especially there was nothing like my tattoos out there," Ms Winzer told news.com.au
The next day after seeing her assistant's quirky pineapple art, Miley also wanted to get inked.
"She got a cat, watermelon, alien and an eyeball β we became friends and she flew me over to Perth to surprise me at her live shows β we ended up partying all night," Ms Winzer said, describing the experience as "surreal".
The young artist went on to become good friends with the singer who often flies her overseas when she wants a new design.
Each of Ms Winzer's tattoos are one-off designs.
"I guess my colours stand out more β I experiment with things some artists would normally be scared to do like creating glitter affects and other weird stuff."
Ms Winzer, who is collaborating with Tech21 to launch its customised range of phone cases, is personally covered with more than 150 tattoos β equating to about $40,000.
"I was always interested in art from a young age, then I began drawing and uploading them to my blog β that's when people started to ask me to turn them into tattoos," Ms Winzer said.
Her breakthrough design was of a crystal tattoo.
Ms Winzer said her rapid success and Instagram popularity came down to "good timing" and doing things "outside the box".
Her long list of celebrity endorsements also include Katy Perry and more recently Post Malone, who had some of his face tattooed by Ms Winzer in January.
"It was a similar situation to Miley β I got a message from Post's people saying he wanted to get a tattoo, but I was sick that day," she said.
"I knew of him but didn't know much about him. Everyone was like you have to do it."
And she did β tattooing the Playboy Bunny icon on his face and Beauty and The Beast dancing in a love heart on his leg.
"He is literally the nicest person I have ever met β for someone who is so young, it blew my mind how much of an old soul he has."
Ms Winzer said despite some ups and downs she is grateful to be in a position where she gets to do what she loves.
"I think it was all good timing and the right opportunities."
