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For a notoriously youth-obsessed industry, fashion has been celebrating the comfortably-retired set with particular enthusiasm lately. Pavement-pounding arbiters of everyman style have been documenting the aesthetic tics of New York’s aging class for years, but appreciation for their particular brand of nonchalant ease has only recently reached its peak. Dressing like a well-to-do septuagenarian has never been cooler.
The touchpoints are obvious: fuzzy cardigans, point collar shirting, high-waisted trousers, and sensible footwear, all mixed and matched with an utter lack of inhibition—an actual carelessness, not that sprezzatura schlock—that comes naturally to the experienced, lasik-enhanced eyes of seasoned dressers. These are clothes that’ll make sitting at home on your couch (or on the subway, begrudgingly commuting back to work) feel a little rich. They’re buttoned-up but not fussy. They’re leisurewear for an entirely different type of leisure, like taking in an exhibit at The Frick at 2 PM on a Tuesday or browsing the cheese selection at Zabar’s to find just the right asiago to complete a Yom Kippur spread. They embody a joyful approach to getting dressed that eschews the soul-deadening banality of corporate lackey attire in favor of boss-man clothing with a dash more seasoning—future heirlooms your progeny will pilfer from your closet while you look on, misty-eyed, from the recliner. (Think Logan Roy, if Logan Roy had slightly less money and slightly jazzier taste.)
What’s driving the trend? An armchair diagnosis might point to an exasperation with the hallmarks of the millennial lifestyle and a yearning for the type of stability that comes with the comfort of regular social security deposits and a cushy 401(k). You might not own a house—heck, you might never own a house—or come by the sort of material trappings so generously doled out to the Boomer generation, but you can dress like you do—no matter what tax bracket you fall into.
The head-to-toe look can be tricky to pull off, but incorporating elements of the aesthetic into your casual everyday rotation is easy enough. (You could do worse than taking a cue from Tyler, the Creator, who swears by a uniform of wacky trapper hats, vibrant sweaters, scrunched tube socks, and sturdy hard bottoms.) Invest in a couple of the pieces here and then wear them like you have absolutely nowhere to be—except a matinee showing and maybe a reading at the 92nd Street Y. But only if you feel up to it.
The Eccentric Literary Type
He penned the definitive tome on a frighteningly specific era of European history. He lives in a tony prewar apartment stuffed to the brim with academic ephemera. He wears this to weekly check-ins with the TAs who—let's be honest—fully run his seminars. You should wear this on a night out.
The Doting Grandparent
He lived frugally, saved wisely, and now mostly spends his time catering to the whims of three nightmarish tots who trek across the park every Sunday for pancakes. He wears this on outings to La Librairie des Enfants. You should wear this to brunch.
The Penitent Titan of Industry
He made a killing in the free-wheeling heyday of '80s Wall Street but donates generously to the NYPL. He says things like "Art is meant to be seen!"—except the Miró in his living room; that's for him alone. He wears this instead of a tux. You should wear this to people watch on Mulberry Street or to meet your significant other's parents—preferably not at the same time.
