Pretty Style is for more mature girls that like high-fashion inspired casual clothing. The content is all targeted towards older teenagers to young adults. I actually like this style of clothing the best myself but for hairstyles, I like Vivi/JJ's styles better :)
Hats are a big trend in Japan for the summer, especially straw hats. It gives your outfit a nice summery casual touch, and of course, it protects your face from the sun!
It is part of the bigger trend that has been going on for the past year: masculine-inspired clothing. By this, I mean vests, fedoras, longer blazers with defined shoulders, etc.
Like it says here, to find similar Chic, high-fashion inspired clothing, try the stores TOPSHOP, H&M, Forever21, Gap, and Zara