Upper East Side Grandmother Is Winter’s Answer to the Summer Coastal Grandma Trend

Tailoring is a cornerstone of the UES aesthetic, and classic black trousers are an absolute must-have. Cigarette-style silhouettes—pants that are slimmer than your traditional straight leg but do not hug the leg all the way down like a skinny jean or legging (think Audrey Hepburn)—are our top pick, but you can opt for a wider leg if you prefer. As for the rise, choose whatever is most comfortable and be sure to add a sleek black leather belt as well.

For many UESiders this would be a long fur coat (or faux fur), but if that’s not really your style, have no fear, there are other options. Rich colors and patterns that look like they’ve been pulled straight from the art at the MoMA are just as fabulous, and you can always add a faux-fur stole across your shoulders for an extra dose of luxury. Just be sure to choose a longer silhouette (it should hit below the knees) to really play up those stealth wealth vibes.

These cute, cropped jackets—most often done in tweed, herringbone or houndstooth with bold buttons and dainty pockets—are proof that you don’t need to spend a lot to look expensive. The design can’t help but call to mind the iconic Paris fashion house, whether you spent $25 or $2,500. To keep those quiet luxury vibes going, wear your jacket with a plain white T-shirt or silk blouse and tailored trousers in a neutral hue.

The Birkin may be the UES grandma’s bag of choice, but there are plenty more affordable styles that are just as sleek to complete your outfit. Opt for solid hues (black will always be most popular) and simple designs that don’t have too much by way of hardware or seaming. A medium-size top handle is a surefire winner, but you can also sport a leather tote if you need more carrying space.

This is where you can start to really let your personality shine. Bold, gold jewelry is the way to go, but you don’t have to stick with classic knot studs or pearl brooches. Look for pieces that feel unique, like they could be an heirloom, with special details you’d be hard pressed to find anywhere else. When in doubt, vintage and secondhand shops will have plenty of oversize rings, intricate necklaces and gaudy earrings to play with.

This doesn’t have to just mean traditional wool blazers and trousers. It can also take the form of cotton skirt suits, silk trousers with smoking jackets or three-piece coordinating sets. Even better if you style your suit with matching accessories for a monochrome look.

No, a silk scarf won’t be as warm as a wool or cashmere one, but these are mostly for fashion rather than function. They should be larger than your average bandana (a 34-inch square is a good size to look for) so that you can elegantly drape them over your shoulders and knot them below your coat collar, or wrapped over your head a la Grace Kelly.