A wise man once said, “you are either in your bed or in your shoes, so it is pays to invest in both.” So as I write this from my comfortable Casper mattress, I thought I could lend some advice on building a strong quiver of leisure shoes. In other words, your daily riders that are worn around town but not meant for exercise, inclement weather, or formality. Who exercises anymore anyway? I Citibike.
Vans: the classic authentic. Durable, affordable, and infinite color options. Best for music festivals, startup offices, and actual skateboarding. My most trusted ally.
Converse: Iconic. Very popular with the bohemian crowd. Like, “I’m posh in my cute white sundress, but I’m also down to sleep in a tent and who cares if my iPhone dies” (dream girl btw). Always get them in white and beat them up a bit before wearing.
Allbirds: the new player. Appropriate but super chill — like your cousin who sold his SaaS startup at 25, went to Stanford Business School, and suddenly pops up in Nadine Leopold’s instagram feed at Beso Beach. Do less, please. Absurdly comfortable while satisfying the “no socks but no smell conundrum” (New Zealand wool, who knew?). Do not wear them for exercising. I blew through the toe in a casual tennis match which I lost (due to the shoes obviously).
Sabahs: chic travel slippers. Like your buddy who has that three day stubble and the perfect unconstructed khaki linen blazer from Al Bazar in Milan. Wear them with a tux or a t-shirt, just don’t wear a tux and a t-shirt.
Top-siders: Sperry only, please do not offend me with a pair of Sebagos or Ralph Laurens. Your options are oatmeal or classic leather for the boaters, anything else and you may as well carry a Trapper Keeper and wear a blue blazer with gold buttons. When rocked correctly, they can defy the preppy stigma and bridge the I live in Bushwick but I went to private school vibe quite well.
Supergas: the elitist. But for no reason except that they are Italian. Practically speaking, exactly the same quality as Vans but twice the price. Often seen at gallery openings and Sweetgreen lines. You will undoubtedly see people smoking cigarettes in these and complaining about how Surf Lodge has become so mainstream. Go with Navy, the safe bet. Like a sunset picture on instagram.
Stan Smiths: timeless, but increasingly basic. Became a little too popular with the fashion set in 2014 and 2015 and are now worn by everyone and their mother. Iterations by every urban fashion designer in town. Simple, yet resilient, like Katniss in Hunger Games. Ironically, Adidas originally created them for top tennis players and now sported exclusively by those who couldn’t tell you what 40-love means.
Tretorns: the exotic. like that hot Swedish girl that came to your high school for a semester and you realized that the world was bigger than your town line. Trendy, waterproof, and an edgy logo that is pretty simple, but gets the head nods from the cools when you walk down Crosby St.
Internationalists: the Nike crown jewel and my kryptonite. Like that fling that remains in the “unfinished business” bucket, you always want more. Limited editions abound (help me find these?), the Internationalists are absolute renegades for when Winter finally arrives. Their reputation speaks for themselves, like Twyin Lannister or J.G. Melon’s cheeseburgers.
Bobbies: oh, you haven’t heard of them? Bobbies was started by a couple ex-finance who realized he could no longer afford Tod’s without their banking bonuses. For your dandy days, with a bouquet of colors, these euro riders are not for the faint of heart.
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