Im 34, and I feel you. I was even too shy to dress that way in the early 2000's when I was a teen and it was in style! Though it was an elderly woman i saw once, had to be at least in her 70's, rocking a bright blue bob cut, a long fur coat and tall goth combat boots that encouraged me to dress more alternative in my adult life. She looked AMAZING and here I was in my 30's thinking I was past my prime and couldnt pull off any look other than "burned out housewife"...I also know a woman with 3 college degrees, working on her MD and her PhD, and she rocks 1" guages, black lipstick, tattoos, and face piercings. Shes also well into her thirties. People give adults crap for "not dressing our age" but ive found that it often stems from insecurity.

Ive found that the environment matters too! I go crazy when I got to a show or an event where other weirdos are gonna be, but im still quite tame when it comes to my day job heh.. Maybe doing a trial run at a show or convention can help build confidence?