I always hate it when people say that they wish they could "pull off" a certain look or piece of clothing. I always think, what's stopping you? Even more so, I hate reading comments on fashion blogs asking for tips and ideas for the "everyday/average/regular girl". Why someone would relegate themselves to the status of average, I have no idea.
Wear what you want! Wear what interests you! Do not confine yourself to the sartorial constraints of the masses!
I think the fascination with street style stems from the fact that the women in the photographs don't bow to the fear of not being able to pull something off. Take the photo above for instance. Ece Sukan knows that she looks cool. The combination of tuxedo jacket-giant bow-white tuxedo shirt could very easily go the route of Janis Ian at the prom but it doesn't because Ece has the right attitude. She does not fear the tuxedo.
The girls you see in street style photos don't possess some superhuman ability to "pull off" clothes. They're simply confident in their personal style and project the kind of confidence that makes the world trust their judgment.