Kylie Jenner is only 16 years old and her sense of style is impeccable. Living in the Kardashian household has definitely influenced her. She wore this outfit out in LA the day she got her hair cut. It has been super cold in NY lately so I put off recreating this outfit. No doubt Kylie's look may cost well over $1k. The total for mine comes out just around $65 but could easily cost less or maybe more depending on where you buy things.
For the skirt, I found this one from Buckle for $30 here or this one from ZooShoo for $22 here
I'm sure Kylie's leather jacket was real/$$$$. I found this from H&M for $50 here
Kylie's boots seem really simple but I couldn't find an exact dupe. I found a few similar from Forever 21. here, here, and here
You should be able to find a simple plain white t just about any where.
Put all of this together and you will look just like Miss Jenner.