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.
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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.
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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.
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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.
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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.
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Shop the matching Eighties High-Cut Bikini Bottoms ($160).
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.
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