I Want to Appear Stylish This Winter Break—6 Outfits That Get It Right
The winter vacation season is nearly upon us. In the upcoming weeks, both airports and roads will be bustling with travelers on their way to their chosen destinations. Some will leave the mountains for beach destinations, while others will swap city living for the suburbs. I'm personally looking forward to visiting L.A., eager for the warmer climate and stunning canyons. I'm excited to pack stylish outfits for the Sunday farmers market, lunch in Malibu, and a New Year's Eve celebration in West Hollywood. To get ready, I’ve been saving outfit ideas from trendy L.A. influencers for inspiration.
While I’m sure you want to look fashionable on your winter getaway, not everyone shares my travel plans. Therefore, I thought it would be fun and useful to provide elegant outfit suggestions for popular winter vacation spots, along with key pieces that can elevate your look with minimal effort. Without further delay, continue reading to find tasteful winter vacation outfit ideas for locations such as Aspen, Miami, Palm Beach, Cabo San Lucas, and more.
**Palm Beach**
Palm Beach fashion is all about understated sophistication—ensembles that appear effortless yet are purposeful and well-planned. If I were vacationing there, I would plan my outfits meticulously instead of randomly tossing in pieces and figuring them out on arrival. For daytime inspiration, check out content creator Ilana Torbiner's look, showcasing a coordinated pants set made of lightweight cotton or linen, paired with flats and a daytime clutch. This outfit is ideal for lunch at the hotel or in town, followed by an afternoon of shopping. When you want to relax outdoors under the sun, think of a simple, minimal swimsuit with a sarong or pants and a straw hat. For evening wear, continue with easygoing styles like patterned dresses, kitten heels, and a lightweight sweater or jacket to drape over your shoulders if it gets cool at dinner.
**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
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**Aspen**
Aspen is a prime destination for luxury shopping and celebrity sightings during winter. Whether you're a frequent visitor or experiencing Aspen for the first time this season, there are certain style tips to keep in mind, depending on your activities. If you’re hitting the slopes at Snowmass, Buttermilk, or Aspen Mountain, you’ll want fashionable ski outfits, like stylish suits and separates from brands such as Perfect Moment, Goldbergh, and Cordova. For shopping days at Kemo Sabe, The Revolve Fwrd Store, or Ralph Lauren, aim for a Western chic vibe with a cowboy hat, long faux-fur coat, jeans, and snow boots. For dinner at places like Caribou Club, Casa Tua, or Matsuhisa, transition your daytime wear to evening attire by swapping winter boots for heels or shifting into leather pants and a stylish blouse topped with 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
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**Cabo San Lucas**
Cabo San Lucas enjoys warm weather this time of year. If you're heading there—lucky you—don't forget to pack your resort attire. For daytime, sunglasses, bikinis or one-piece swimsuits paired with linen beach pants, a button-up shirt, and a raffia clutch work perfectly for a seamless transition from beach to pool bar. For dinner, whether in town or at your hotel, opt for a coordinated 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
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I Want to Appear Stylish This Winter Break—6 Outfits That Get It Right
Whether you're heading to Miami, Aspen, or any other destination.