Planning a getaway? We have just what you need: suggestions for the comfiest, cutest dresses to take you from the airport to the beach…or even the ski lodge! Check out our suggestions and let us know what you’re wearing this winter season.

Going Somewhere Warm?

Our short, light-colored wrap dress will keep you comfy on the plane, as it’s a scrumptiously soft bamboo/cotton blend. Then throw on a floppy hat, swap your shoes for flip-flops, and hit the beach. The best part is that the dress is UPF 50+, so you’ll have excellent protection from the tropical sun. It’s also a stylish cover-up if you want something to slip over your bathing suit.

Or rock our plum sleeveless maxi dress on your warm-weather trip! You can easily cover up your shoulders with our Endless Summer Scarf, whether you get chilly on the plane or need to protect your skin from the sun’s rays.

For those tropical trips that require lots of walking, choose sandals with back straps and/or arch support rather than flimsy flip-flops. Hey, no one said comfort and style had to be mutually exclusive!

Going Somewhere Cold?

If you’re bound for a winter wonderland, layer up! A turtleneck knit dress will keep you toasty, whether you’re traipsing through the Colorado mountains, exploring Iceland, or just heading across town. For maximum warmth, wear fleece-lined leggings and a long wool coat.

Going to See Relatives or In-Laws?

A maxi dress will keep you comfortable yet looking pulled together. Pair it with your best dress coat and conservative black boots. If you choose a maxi in a vibrant color, stick to neutrals for your accessories and outerwear. If you do incorporate color, stick to small doses echoing your main shade. Get ready for the compliments!

Going to a Party?

The short black wrap dress is equal parts sexy and classy. If you work in a formal environment, you won’t get any disapproving looks, but it’s not like you’re wearing a nun’s habit, either. You can easily dress it up with sky-high heels or knee high boots, or keep it dressy with conservative kitten heels.

Accessorizing is the fun part, because you have unlimited options with a black dress. You can choose accessories in warm tones, like crimson, copper, and gold. That’s your best bet if you have a warm skin tone or you’re a redhead. If you look best in blues and grays, accessorize your LBD with silver, white, or a touch of icy blue (think Frozen for grown-ups!).

Whatever color scheme you go for, a black dress with a V-neck means you have room to play with necklaces. With the style above, you want a shorter statement necklace or a long, delicate chain. The former gives you a chance to draw people’s eyes to your face — gems matching your eye color do this easily.

No matter what you wear, have a fantastic winter season, and safe travels from all of us at SummerSkin!

How are you styling dresses this winter? Share your tips for staying chic yet cozy in the comments!

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Based in Portland, Oregon, SUMMERSKIN is a line of stylish women's lifestyle apparel and accessories with sun protection built-in.

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