A winter vacation can mean two completely different suitcases. A snowy mountain town needs warm layers and boots. A beach escape in December needs swimwear and sundresses, plus something for the cold airport you're leaving. Here are stylish winter vacation outfits for both kinds of trip, with day-to-night formulas and packing tips so you don't overpack.
Cold-weather destinations: ski towns, snowy cities, holiday markets
The goal is warmth without looking bulky. Build every outfit from three layers: a fitted base, a warm middle (a sweater or knit), and a statement outer layer.
Daytime: the puffer, the knit, the jeans
A glossy puffer jacket is warm, packs down small, and looks great in snow photos. Wear it over a cozy sweater and stretch skinny jeans tucked into winter boots.
Shop the Green Glossy Puffer Jacket
Shop the Teddy Pair To Compete Sweater
Shop the Super Smoothing Stretch Skinny Jeans
Cabin and lounge days: the knit jumpsuit
A hooded knit jumpsuit is one piece that works for the cabin, the hotel lounge, and the flight home. Add a puffer and sneakers to go out for coffee.
Shop the Chancy Hooded Knit Jumpsuit
Après-ski and dinner: velvet or satin under a coat
Evenings in a winter destination usually happen indoors, so you can wear a dress. Velvet is warm and festive; satin is lighter and packs flat. Pair either with sheer tights, knee boots, and your puffer or a long coat for the walk over.
Shop the Vivian Floral Velvet Mini Dress
Shop the Slip Into Satin Mini Dress
Warm-weather winter escapes: beaches, islands, cruises
Trading snow for sun? Pack like it's summer, but dress for the cold airport on the way out. Wear your heaviest pieces (jeans, sweater, jacket) on the plane so your suitcase stays light.
Day: swimwear and an easy cover-up
Bring two or three swimsuits so one is always dry, plus a cover-up that doubles as a lunch outfit. Browse the full Swimwear collection, including Plus Size Swimwear.
Day to night: a linen jumpsuit
A strapless linen jumpsuit goes from the beach bar to dinner with a change of shoes and a pair of earrings.
Shop the Criss Linen Cotton Strapless Jumpsuit
Night: a satin maxi
For a resort dinner or a cruise formal night, a high-slit satin maxi feels special and packs into almost nothing.
Shop the High-Slit Satin Maxi Dress
Winter vacation packing checklist (5-day trip)
| Cold destination | Warm destination |
|---|---|
| 1 puffer or warm coat | 2–3 swimsuits |
| 2 sweaters | 1 cover-up |
| 2 pairs of jeans | 1 linen jumpsuit or set |
| 1 knit jumpsuit for lounging | 2 sundresses |
| 1–2 velvet or satin dresses for dinner | 1 satin maxi for a dressy night |
| Winter boots, tights, scarf, gloves | Sandals, one dressy shoe, sun hat |
Packing tips that save space
- Wear your bulkiest pieces on the plane.
- Choose one color story (for example black, cream, and one bright) so everything mixes.
- Satin and jersey roll without wrinkling; velvet should be folded inside out.
- Pack one outfit in your carry-on in case your bag is late.
Shop more for your trip in Jackets & Sweaters, Women's Jeans, and Vacation & Resort Wear. Going somewhere for the holidays? Our Holiday Party Dresses guide covers the parties too.