I think skinny jeans and heels are more or less the only option to make it look feminine, even though I admit she looks great with flats, but you have to be really skinny to pull of the combination of flats and skinny jeans.
Olivia looks perfect. However I'd add some studs to the jacket to make mine unique and personal. I would definitely wear it with some skinny jeans and boots in the winter and a pair of ripped denim shorts and flip flops In the summer. It's perfect for all year round!! Love it.