why I love it: I wouldn't consider myself preppy, but I've always loved the shape of the classic boat shoe. I have a pair in mid-brown that goes with absolutely everything once it's warm enough to shed boots, and they do well with water on days that rain boots just aren't going to happen. Sometimes the neutrals just don't cut it, though, so when I saw this pair on Esquire, all I could do was hope they came in women's as well. They don't, but that doesn't mean I'm not still obsessed with them. The all black top makes the neon sole pop, which is the whole point of the shoe, while still being the classic shape and extremely versatile for everyday wear. These shoes can do the work for you in an outfit, and I'm just hoping and praying that I get note of the women's version soon, because they don't make men's sizes small enough (yes, I checked).
where to get it: Unfortunately, they're not listed on the Sperry website, but there are a few sizes left on Zappos, $90