Older siblings: Khloé Kardashian, Kim Kardashian, Kourtney Kardashian, and Kendall Jenner
On a recent episode of Keeping Up With the Kardashians, after Kylie had purchased her first house, her older sisters sat her down and lectured her about how much work and responsibility it takes to be a homeowner. This is one example of Kylie's naiveté coming into play, as younger siblings tend to be more coddled and taken care of, while also having the most freedom. As the baby of the Kardashian-Jenner clan, Kylie has tons of people to turn to for advice but often eschews their guidance in favor of going her own way and doing her own thing. Her little-sister status also explains her willingness to experiment with her clothes, hair, makeup, and yes, cosmetic surgery.