One rule any transplant to New York learns right off the bat: never, ever wear flip flops outside for a trip longer than shuffling to the corner deli and back. And probably not even then. The list of reasons to avoid flip-flops in the city is long, gross, and best not dwelled upon.
This raises a major question of how to replace this go-to summer footwear, and for this, allow me to introduce you to your new best friend, the Sperry Top-Sider boat shoe. A decades-old preppy staple, boat shoes have made a huge comeback over the past several seasons, and with good reason: possibly the most versatile shoe in existence, not only do these look good on ladies and gents of all ages, they’re comfortable for as much strolling (or sauntering) as you’re capable of managing in the heat. A lot of knockoffs have cropped up with their resurgence in popularity, but don’t be fooled, Sperry always has been and always will be the gold standard when it comes to boat shoes.
For such a simple shoe there’s a huge amount in variation between style with these. So far I’ve stuck with a classic dark brown pair, but I’m also feeling this updated color-blocked pair for a little bit of a twist on the look.
And, in case you want to feel like you’re on a yacht, in Miami, or on a yacht in Miami (and really, who doesn’t?), these white ones couldn’t possibly be better:
