Illustrations courtesy of Angela McKay

Wish You Were Here:
A Style Guide to Three
of Our Favorite Cities

In partnership with our friends at

Half the fun of a trip out of town is packing—imagining the fun mornings, the afternoon strolls, the long, decadent dinners, and what you’ll wear for every one of them. We set our sights on three American cities, each with a rich history and a strong personality, and selected the pieces that perfectly complement each. Also along for the ride: the Gucci Arli bag that’s exactly right for exploring museums, discovering new restaurants, and staying out too late.

• CHICAGO

• It’s the only big city that can also lay claim to Midwestern charm—so a trip to Chicago means versatility: sleek leggings, cool kicks, and a burgundy leather top-handle bag big enough to stash a pair of warm gloves and a scarf. While you’re there, be sure to check out the Art Institute and the Renzo Piano–designed Modern Wing and, if you can, tour Frank Lloyd Wright’s iconic home and studio in Oak Park. Finish the day with drinks at Soho House and dinner at Elske for a Scandinavian-inflected meal.
• 
• GUCCI Arli Large top handle bag Gucci, $3,200
• GUCCI bracelet Gucci, $1,520
• GOOP BODY OIL goop, $60
• A culture fix at:
  Art Institute of
  Chicago
• GUCCI high-top sneaker Gucci, $1,250
• GUCCI tweed bomber jacket Gucci, $4,500
• LEMAIRE SKIRT goop, $794
• Drinks at:
  Soho House Chicago
• GUCCI wool gloves Gucci, $415
• A tour through:
  Frank Lloyd Wright’s
  Home and Studio
• Dinner at:
  Elske

• DALLAS

• There’s nothing subtle about Dallas, which is exactly what gives this city its character. While we’re in town, we love to shop for charming home items and flowers at Grange Hall, stroll among Rodin and Richard Serra masterpieces at the Nasher Sculpture Center, hang by the pool at the Rosewood Mansion on Turtle Creek, and indulge in some of the best sushi anywhere at Uchi. It’s a trip (and a city) made for bold statements and bright colors—turquoise floral jackets, hot-pink skirts, and a crisp, white-and-gold Arli bag.
• 
• GUCCI arli small shoulder bag Gucci, $1,980
• GUCCI mules Gucci, $790
• A swim at:
  Rosewood Mansion on
  Turtle Creek
• GUCCI silk skirt Gucci, $2,200
• Shop at:
  Grange Hall
• GUCCI silk jacket Gucci, $4,500
• GOOP FRAGRANCE
  EAU DE PARFUM: EDITION
  04 – ORCHARD goop, $55-165
• GUCCI ring Gucci, $1,050
• A culture fix at:
  Nasher Sculpture Center
• Dinner at:
  Uchi

• SAN
  FRANCISCO

• The famous fog that tumbles down the hills onto the city makes for beautiful pictures—and chilly nights. It’s a perfect reason to throw on a cozy sweater, grab your crossbody bag (which is ideal for running around town), and settle in for a long, luxurious supper at Leo’s Oyster Bar. Afterward, head back to your room at the Hotel Drisco in Pacific Heights and turn on a movie in keeping with San Francisco’s darkly romantic vibe, like the Hitchcock thriller Vertigo.
• 
• GUCCI bag Gucci, $2,500
• RMS BEAUTY luminizer goop, $38
• Shop at:
  Ayla
• REJINA PYO skirt goop, $370
• GUCCI wool coat Gucci, $3,500
• Dinner at:
  Leo’s Oyster Bar
• GUCCI sweater Gucci, $1,700
• Watch:
  Vertigo
• GUCCI yellow gold ring Gucci, $1,550
• GUCCI leather ankle boot Gucci, $1,690
• Check in at:
  Hotel Drisco