As much as I love my flats, sometimes even they don't quite cut it comfort-wise.
I've wanted a pair of high-top sneakers for a while, but it's been hard to find some that fit with my personal style, which is decidedly not high-top friendly. I found this pastel pair of Supras on accident while surfing the Internet and knew pretty much instantly that I had to have them. I can picture wearing them as easily with skinny jeans as I could with shorts.
Also, if this sort of thing matters to you, Niall Horan from One Direction wears Supras, like, all the time.
Supra Skytops in Shrinking Violet, $85.99, available at Zappos.