This Italian Date Night is 560 Years in the Making

Some date plans are risky. This ain’t one of them.

You’ll be sporting fine wintry threads from a freshly opened menswear joint on the UES.

You’ll be treating yourselves to a truffle extravaganza nonpareil.

And then you’ll be cruising to the must-see cultural event of the season.

We’re impressed with you just writing this.

The Fit
Certain outfits perfectly embody the spirit of the season. In spring, we believe it’s a sweatshirt, shorts and loafers. But on the cusp of fall-winter, it’s this: a classy turtleneck-blazer combo from the freshly opened J. Press on the Upper East Side. Pair with shiny kicks from The Armory’s first in-house shoe collection and you’re in business.

truffle (3 images)

EAT
Truffle season conveniently coincides with the time of year waistbands miraculously become elastic. Our favorite spot to indulge is Rossopomodoro, who work with heritage Italian truffle purveyors Urbani to create a decadent seasonal menu with truffled steak, pizza, pasta and even a sigh-inducing dessert concoction, complemented by unusual, exciting wine pairings (also worth noting they have a surprising number of exceptional gluten-free options). Truffles fetch about $4K a pound right now, so when you see one the size of your fist tableside, play it cool.

DO
This is not for your Instagram. It’s not the damn Museum of Color or Ice Cream or Selena Gomez. This is art of the highest pedigree on earth: 133 original sketches, studies and drawings by a fellow called Michelangelo. It’s an unprecedented exhibition of the Renaissance master’s work, the likes of which this world has never seen and likely will never see again. It’s here for three months. Don’t deal in regrets. Get thee to the Met.