How did you find the confidence to start wearing whatever you want to wear?

I need help. I grew up with my military strict dad and my tomboy sister. I loved skirts and dresses but he wanted us to always dress in pants and boyish clothes. When i ripped my jeans because i wanted to be stylish like other kids, he got pissed (i can see why) but still i never was able to express myself and was forced to wear my sisters ugly hand me downs. Kids and other little girls would even ask me if i was a boy. I was shy growing up, wasnt the cutest kid or even in high school. After i turned 18, im not sure what happened but i turned hot. I have a fit slim body, nice butt, green eyes, soft curls, and olive skin, that ive started to embrace myself. My body is on point, i get attention that i never did before. As im a bit older now, 23 i want to start dressing cute! I always stick to jeans and a t shirt when i go out :( i have cute Pinterest boards of outfits that i LOVE but i cant get myself to wear them because i fear the judgment from others or i feel people will think “who’s she trying to fool or impress.” Whenever i go shopping with people they always tell me i will look good in anything and get jealous of me. I just never experimented with my style and am nervous to. Anyways how can i get to this point? Clothes are expensive also, so its not like i can spend thousands trying to find clothes to fit my wardrobe. I think i know my style, but i always stick to whats comfortable, my jeans t shirt and sneakers and end up feeling average and below everyone else.

Also my last relationship, he was 30 and im 23. I wanted to look mature and classy, put together. I was able to throw some nice outfits together. But not many. I’m just not entirely there. Im also a mom, and became a mom at the age of 20, so that stunted my “fashion growth.” Im not with the times. Any advice?