30 Best Winter Dresses For Every Occasion, From Casual Outings to Holiday Parties

Frost is slowly nipping at our noses, which means our slouchy winter jackets and over-the-knee boots are back in the wardrobe rotation. As you swap out your fall dresses with their wintry counterparts, consider upgrading some of your favorite styles.

Throughout the chilly months ahead, you might opt for long-sleeve sweater dresses, velvet dresses for a more festive feel, or maxi dresses for extra coverage. We’ve rounded up a range of trending silhouettes appropriate for various occasions, from casual outings and work to holiday parties and winter weddings. From comfy-cozy frocks to bedazzled gowns, the best cool-weather dresses from reliable reader-favorite brands like J.Crew, Anthropologie, Zara, Abercrombie & Fitch, and Madewell are ahead.

Whether you’re dressing for the office, casual dinners, log cabin escapes, or holiday market shopping, a sweater dress will serve you well. There’s a lot of variety, from jersey to cashmere knit, and lightweight to thick — but all these cozy styles will keep you warm and comfortable throughout the season. We’ve found the best new sweater dresses in a range of lengths and colors, such as a long-sleeve button-up frock that doubles as a long cardigan for work, a red maxi for winter festivities, or an off-the-shoulder mini dress for date night.

We’re already thinking ahead to which holiday party dresses we want to wear to our White Elephant gift exchanges, New Years Eve celebrations, and everything in between. If the occasion calls for some sparkle, opt for chunky sequins or shiny satin. For events like office gatherings and at-home Christmas dinners, you can pick up styles featuring  stretchy shirred bodices and casual takes on tulle that are still festive, but a bit more comfortable and versatile.

When we think of winter fabrics, our minds automatically go to velvet. It’s soft, smooth, and simply scrumptious — a great option for cocktail events and winter weddings, especially in a fitted midi or maxi dress silhouette. We also found minis with fun details like fluttery sleeves, lace collars, and trendy bows for a range of other winter festivities, like potlucks and NYE parties. 

If you’ve got weddings approaching and still don’t have a wedding guest look, we’ve got you. Look out for rich jewel tones and classic black dresses with a twist (think bows and off-the-shoulder necklines). If the nuptials require cocktail attire, consider a mini or midi dress that’s chic and versatile enough to wear again at other winter parties. A black-tie dress codes calls for a gown, but you get bonus points if it’s in a festive color and bedazzled to the max.

Maxi dresses aren’t just for the summer — in fact, they’re arguably ideal for winter, as the ankle-skimming, floor-grazing styles will keep your legs shielded from the frigid air. For casual occasions, lounge dresses and long sweater dresses are great. And for more formal events, look for elevated turtlenecks and off-the-shoulder necklines. We’re especially eyeing trendy burgundy styles, to bring the fall color into winter.