It’s almost that time of year—winter vacation. In the coming weeks, airports and highways will be crowded with travelers heading to their planned destinations. Some will escape the mountains for the beach, while others will trade the city for the suburbs.
Personally, I’m heading to L.A., and I’m so excited about the warmer weather and the canyons. I also look forward to packing elevated outfits for the Sunday farmers market, lunch in Malibu, and a New Year’s Eve party in West Hollywood. To prepare, I’ve been bookmarking outfits from chic L.A. fashion insiders for inspiration.
While I’m sure you also want to look stylish on your winter vacation, not everyone has the same destination plans as I do. So I thought it would be fun and helpful to share elegant outfit ideas for popular winter getaway spots, along with hero pieces that will make you look stylish with minimal effort. Without further ado, keep scrolling to discover tasteful winter vacation outfit ideas for spots like Aspen, Miami, Palm Beach, Cabo San Lucas, and more.
Palm Beach
The fashion in Palm Beach is all about understated elegance—outfits that feel effortless but are definitely intentional and well-thought-out. If I were vacationing here, I would carefully style my look rather than packing random pieces and figuring out how to put them together when I get there. If you need some inspiration, especially for the daytime, look at content creator Ilana Torbiner’s outfit, seen here in a matching pants set in lightweight cotton or linen with flats and a daytime clutch. This is the kind of outfit that’s perfect for lunch at the hotel or in town and then spending the afternoon shopping. When you want to sit outside and soak up some sun, think simple, minimalist one-piece swimsuit with a sarong or pants and a straw hat. For the evening, easy, breezy pieces continue with patterned dresses, kitten heels, and a lightweight sweater or jacket to throw over your shoulders in case you get chilly at the restaurant.
Shop the look:
Enza Costa
Linen Strapless Tunic
Enza Costa
Everywhere Pants
Havaianas
Slim Flip Flops
J.Crew
Portofino Handknotted Clutch
More winter vacation essentials for Palm Beach:
Good American
Always Fit Bikini Top
Bananhot
Shawn Mesh Pants
Reformation
Clara Cashmere Crew Cardigan
Tony Bianco
Caprice Heels
Aspen
From luxury shopping to celebrity hot spots, Aspen is the place to be and be seen during winter. So whether you’ve been to Aspen a few times or are visiting for the first time this season, there are a few things to know about what to wear, but it also depends on your plans. If you’re skiing Snowmass, Buttermilk, or Aspen Mountain, you’ll want the chicest ski outfits, like suits and separates from brands such as Perfect Moment, Goldbergh, and Cordova. For days spent shopping at Kemo Sabe, The Revolve Fwrd store, or Ralph Lauren, go for Western chic—such as a cowboy hat, a long faux-fur coat, jeans, and snow boots. For dinner at Caribou Club, Casa Tua, or Matsuhisa, you can transition your daytime looks to evening by swapping your winter boots for pumps or switching into leather pants, a blouse, and a long leather trench coat.
Shop the look:
AZALEA WANG
Faux Fur Coat
levi’s
Low Loose Women’s Jeans
Aritzia
Wildwest Cattleman Cowboy Hat
More winter vacation essentials for Aspen:
Halfdays
Hedy Ski Puffer Jacket
Zella
Live in High Waist Leggings
ZARA
Quilted Ankle Boots Ski Collection
CULT GAIA
Michelle Cardigan
Madewell
The Longline Straight Jeans
Cabo San Lucas
Cabo San Lucas is known for its reliably warm weather during this season. If you’re heading there—jealous—be sure to pack your resortwear. For daytime activities, sunglasses, bikinis or one-piece swimsuits paired with linen beach pants, a button-up shirt, and a raffia clutch are perfect for going from the beach to the pool bar. For evening dining, whether at your hotel or in town, choose a matching skirt set or a dress with open-toe heels.
Shop the look:
Lovers and Friends
Chasing Sunsets Top
ASOS DESIGN
Linen Look Pull on Pants
ZARA
Wide Sleeve Linen Shirt
More winter vacation essentials for Cabo San Lucas:
ESCVDO
Safi Scalloped Crocheted Cotton Top
ESCVDO
Safi Scalloped Crocheted Cotton Midi Skirt
Janessa Leone
Cami Black Bag
MANGO
Knitted Dress With Sequin Detail
Jeffrey Campbell
Go-Getter Sandal
Valentino Garavani
Devain Small Shoulder Bag
New York City
New York City attracts winter vacationers with its dazzling lights, festive windows, and of course, the iconic Times Square ball drop. But for those visiting, don’t be fooled by its beauty; the weather will likely be in the teens. To handle the freezing temperatures with style and look like a local, rely on an all-black palette—a fail-safe technique. Think black leather pants, a thick wool coat, sock ankle boots, leather gloves, and a thick scarf.
Shop the look:
MANGO
Wool-Blend Funnel-Neck Coat
gap
Organic Cotton Poplin Big Shirt
DAZE
Sundaze High Waist Straight Leg Faux Leather Pants
Treasure & Bond
Cozy Sparkle Fringe Scarf
Reformation
Remy Stretch Ankle Boot
Saint Laurent
Jamie 4.3 Pochon Bag
More winter vacation essentials for New York City:
Le Bop
Double V Neck Pullover Sweater
Pistola
Cassie High Waist Crop Straight Leg Jeans
UGG
Classic Micro Genuine Shearling Lined Slip-On
ALIGNE
Dara Collarless Jacket
Vince
Leather Straight Skirt
Nordstrom
Cashmere Lined Leather Touchscreen Gloves
Miami
Compared to Palm Beach, Miami’s fashion style tends to be more playful with a definitely party-ready vibe, especially when New Year’s celebrations are near. So if your winter vacation plans bring you to Miami this year, take a cue from influencer Coco Schiffer, who just celebrated her birthday there, and choose a chic slip-skirt outfit. This kind of look can easily go from a fun group dinner to the club—or your bed. During the day, keep it casual but stylish since you’ll probably be lounging on the beach but still want to show your friends and anyone you bump into that you have good taste. And of course, expect to order Joe’s Stone Crab and Aperol spirits directly to your seat.
Shop the look:
Bella Venice
The Jessie Slip Skirt
Shashi
Cameron Hoop Earrings
More winter vacation essentials for Miami:
Anemos
Classic Triangle Bikini Top
DEVON WINDSOR
Leiza Maxi Dress
Heaven Mayhem
Sloane Sunglasses
STEVEMADDEN
Playing Black Suede
Courchevel
For a winter vacation in Courchevel, the French Alps, think alpine elegance mixed with practical warmth. Pack sleek, high-performance ski layers for the slopes, such as thermals from the viral The North Face x Skims collection, an Aritzia puffer jacket, and Moon Boots to get you to and from the slopes in style. In the evenings, Courchevel calls for cozy-chic separates, such as a wool coat, Fair Isle sweater, dark-wash jeans, and fur-lined boots.
Shop the look:
The North Face X Skims
Refina Bodysuit
More winter vacation essentials for Courchevel:
Massimo Dutti
100% Wool Jacquard Knit Sweater
J.Crew
Wide-Leg Trouser in Washed Velvet
FP Movement
Downhill Diva Suit
prada
Re-Nylon and Shearling Mittens
Nordstrom
Rib Cashmere Beanie