I know a lot of you are either planning or starting to pack for a winter vacation. Whether you’re getting out of town for a weekend and heading to the mountains or taking a week-long ski trip, I wanted to share a roundup of three winter vacation outfit ideas for every occasion. There is a comfortable and cozy outfit to wear all day, a versatile outfit you can wear on and off the slopes, and a dressier cold weather look for the evening.

Cozy & Casual Winter Vacation Outfit

Winter Vacation Outfit Ideas - Cozy & Casual.

Stripe Turtleneck Sweater / High Waisted Jeans / Jacket / Pom Pom Beanie / Earrings / Sunglasses / Winter Boots

This cozy and casual winter vacation outfit is the perfect daytime look for sightseeing or shopping. I love this black and white striped turtleneck sweater. The ribbed hem and sleeves are such a beautiful detail. I’d wear it with a pair of high waisted jeans and a leather puffer jacket. Accessorize with mini pearl hoop earrings, a warm cable knit pom pom beanie, and tortoise sunglasses. This pair is under $30. Then lace up your winter boots, and you’re ready to head out the door. This look doubles as a great winter travel outfit too.

Slopeside Winter Vacation Outfit

Winter Vacation Outfit Ideas - Slopeside Style

Fair Isle Mock Neck Sweater / Warm High Waisted Leggings / Belted Puffer Jacket / Sunglasses / Pom Pom Beanie / Winter Snow Boots

If you’re going on a ski trip, this outfit would be great for staying warm on and off the slopes. The key to staying warm while skiing is layers, and the challenge is how to bundle up while still looking cute, haha. Start with this wonderfully soft fair isle print mock neck sweater. Depending on how cold it is, you may even want to layer a long sleeve thermal shirt under it too. Then I’d wear these high waisted leggings under your ski pants. They’re extremely warm, and the brushed interior feels so soft. I love the look of this white belted puffer jacket, and it’s so chic. Then after a long day of skiing, switch out your ski boots for these super warm winter snow boots, throw on a pair of sunglasses and a pom pom beanie, and you’re ready for après ski.

Dressy Winter Vacation Outfit

Winter Vacation Outfit Ideas - Evening Dinner

Cashmere Cable-Sleeve Sweater / Tiered Maxi Skirt / Parka Coat / Crossbody Bag / Mini Hoop Earrings / Waterproof Block Heel Bootie

If you’re looking for something a little more dressy that you can wear out to a nice dinner or event, I love this outfit. Start by tucking this cashmere cream cable knit sleeve sweater into a maxi skirt. This skirt has flowy tiers and the most beautiful floral print. I’d wear it with a neutral colored parka coat and a neutral crossbody bag. I absolutely LOVE this bag. And accessorize with gold jewelry like these mini hoop earrings. You can opt to wear a bootie or a pair of taller riding boots. I’m eyeing these block heel booties because not only are they cute, but they’re waterproof, so you don’t have to worry about what happens when you inevitably walk through some wintery slush.