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
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