Style

snowy city street

Kicking Off the Holidays from NYC to Italy

In partnership with our friends at Banana Republic

Being adorable all summer is easy. Days are long, florals are everywhere, and golden hour shows up nightly. But what about winter? That takes classic beauty, a special brand of quirky charm, and a festive streak. Below, three cities that have it going on year-round—plus why we think they’re at their best when the temperatures are on their way down.

Chicago Bean Chicago Bean

CHICAGO

Late fall looks good on the Windy City: Millennium Park perks up the skyline with a giant Christmas tree, an ice-skating rink springs up, and selfies under the Cloud Gate sculpture just look better when you’re bundled up. Our take on a Chicago uniform? An oversize camel coat, a burgundy beanie, and slick sneakers peeking out from winter-white wide-legs. Even more reason to book a trip: It’s technically the low season—the best time to upgrade to a suite at the Peninsula. Cozy up at Longman & Eagle with a whiskey, order a dose of escapism at Fat Rice, or pick up an extra layer at goop MRKT on Oak Street.

What to Pack

  1. Sophie Ratner Bracelet Sophie Ratner Bracelet
    Sophie Ratner Bracelet goop, $2,780
    SHOP NOW
  2. Banana Republic Beanie Banana Republic Beanie
    Banana Republic Beanie Banana Republic, $68
    SHOP NOW
  3. Banana Republic Coat Banana Republic Coat
    Banana Republic Topcoat Banana Republic, $299
    SHOP NOW
  4. Banana Republic Shirt Banana Republic Shirt
    Banana Republic Shirt Banana Republic, $80
    SHOP NOW
  5. Mother Pants Mother Pants
    MOTHER Pants goop, $228
    SHOP NOW
  6. MM6 Sneakers MM6 Sneakers
    MM6 Sneakers goop, $480
    SHOP NOW
Central Park Central Park

NEW YORK CITY

NYC during the holiday season will convert even the nonfestive types—or at least make them appreciate the Met Christmas tree. And it makes sense—what kind of person can remain uninspired when the day starts with a trip to Russ & Daughters and ends at the Wythe Hotel rooftop? Here’s what to do with the hours between bagel o’clock and half-past martini: Keep it simple. A high-neck blouse that looks chic under a sweater (for cocktails at the Carlyle), a trench and trousers that hit that street-style-meets-lady-on-the-move note (for dinner at Wildair), and bright-white low-tops cool enough for a slice at Roberta’s.

What to Pack

  1. Vram Hoops Vram Hoops
    Vram Hoops goop, $3,900
    SHOP NOW
  2. Nili Lotan Coat Nili Lotan Coat
    Nili Lotan Coat goop, $795
    SHOP NOW
  3. Banana Republic Sweater Banana Republic Sweater
    Banana Republic Sweater Banana Republic, $99
    SHOP NOW
  4. Sea Blouse Sea Blouse
    Sea Blouse goop, $275
    SHOP NOW
  5. G. Label Kelly Wide-Leg Trousers G. Label Kelly Wide-Leg Trousers
    G. Label Kelly Wide-Leg Trousers goop, $495
    SHOP NOW
  6. Common Projects Sneaker Common Projects Sneaker
    Common Projects Sneakers goop, $416
    SHOP NOW
Rome Colosseum Rome Colosseum

ROME

Whether you prefer your holiday grandeur old-school at Vatican City or new at Palazzo Fendi, the Eternal City is stunning in December—and the epicenter is the Christmas market at Piazza Navona. Hit the famous spot in a pair of flat boots, a crossbody bag with a clasp, and layered textures: a faux-fur jacket, a slouchy sweater, a soft knit scarf. Find a mulled-wine vendor, then jump right in—once you’ve hit sensory overload, analyze your mood. Do you want to eat and drink in an ancient cave? Head to Hostaria Costanza. Ready to carb-load for tomorrow’s walking tour? Retrobottega for organic pasta. Either way, you deserve lunch in the Roman tradition, with plenty of courses and just as much wine, enjoyed over multiple, luxuriously casual hours.

What to Pack

  1. Banana Republic Scarf Banana Republic Scarf
    Banana Republic Scarf Banana Republic, $58
    SHOP NOW
  2. Banana Republic Bag Banana Republic Bag
    Banana Republic Bag Banana Republic, $198
    SHOP NOW
  3. Totême Jacket Totême Jacket
    Totême Jacket goop, $550
    SHOP NOW
  4. G. Label Yang High-Cuff Turtleneck Sweater G. Label Yang High-Cuff Turtleneck Sweater
    G. Label Yang High-Cuff
    Turtleneck Sweater
    goop, $595
    SHOP NOW
  5. Rejina Pyo Skirt Rejina Pyo Skirt
    Rejina Pyo Skirt goop, $550
    SHOP NOW
  6. Acne Studios Boots Acne Studios Boots
    Acne Studios Boots goop, $690
    SHOP NOW
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