Holiday Midi Dresses

Holiday midi dresses bring timeless style and lasting comfort to every celebration. Designed for everything from cozy family gatherings to festive evenings out, these versatile dresses offer an easy way to look and feel your best all season long. With a range of classic colors and cheerful prints, holiday midi dresses make it simple to find the right look for any occasion—so you can focus on making memories that matter most.

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298 Items

Women's Cloud Gauze Midi Dress, Stripe
Price was from: $89 now: $74.99

A lightweight, crinkled cotton midi dress in colorful stripes with a V-neckline and adjustable drawstring waist.
Women's Cloud Gauze Midi Dress

A breezy white midi dress in lightweight crinkled cotton gauze with a V-neck and adjustable waist.
Women's Signature Camp Flannel Midi Dress

An irresistibly soft purple cotton flannel midi dress with herringbone texture and removable tie belt.
Women's Cloud Gauze Midi Dress
Price was from: $79 now: $49.99

A breezy, deep sea midi dress made from 100% cotton gauze with a relaxed fit and side slits.
Women's Cloud Gauze Midi Dress
Price was from: $79 now: $49.99

A breezy deep sea midi dress in 100% cotton gauze with a relaxed fit and side slits.
Women's Cloud Gauze Midi Dress
Price was from: $79 now: $49.99

A breezy white midi dress in 100% cotton gauze, perfect for poolside or casual outings.
Women's Cloud Gauze Midi Dress
Price was from: $79 now: $49.99

A breezy deep sea cotton midi dress with a relaxed fit, perfect for poolside or lunch outings.
Women's Cloud Gauze Midi Dress
Price was from: $79 now: $49.99

A breezy blue midi dress made from 100% cotton gauze, perfect for poolside or casual outings.
Women's Cloud Gauze Midi Dress
Price was from: $79 now: $49.99

A breezy blue cotton midi dress with a relaxed fit, perfect for poolside or casual outings.
Women's Cloud Gauze Midi Dress
Price was from: $79 now: $49.99

A chic black midi dress in 100% cotton gauze, perfect for poolside or casual outings.
Women's Cloud Gauze Midi Dress
Price was from: $79 now: $64.99

A lightweight orange cotton midi dress with a crinkled gauze texture, V-neckline, and adjustable waist.
Women's Cloud Gauze Midi Dress, Stripe
Price was from: $89 now: $74.99

A lightweight, crinkled cotton midi dress in colorful stripes with a V-neckline and adjustable drawstring waist.
Women's Cloud Gauze Midi Dress

A lightweight white midi dress in crinkled 100% cotton gauze with a V-neck and adjustable waist.
Women's Cloud Gauze Midi Dress

A lightweight white cotton midi dress with a crinkled gauze texture, V-neckline, and adjustable drawstring waist.
Women's Cloud Gauze Midi Dress

A lightweight blue cotton midi dress with a crinkled gauze texture, V-neckline, and adjustable waist.
Women's Cloud Gauze Midi Dress, Stripe
Price was from: $89 now: $74.99

A lightweight green cotton midi dress with colorful stripes, crinkled gauze texture, and adjustable waist.
Women's Cloud Gauze Midi Dress

A lightweight blue midi dress in 100% crinkled cotton gauze with a V-neck and adjustable waist.
Women's Signature Camp Flannel Midi Dress

A brown cotton midi shirt dress featuring soft flannel, herringbone texture, and a removable tie belt.
Women's Cloud Gauze Midi Dress, Stripe
Price was from: $89 now: $74.99

A lightweight green cotton midi dress with colorful stripes, crinkled gauze texture, and adjustable waist.
Women's Signature Camp Flannel Midi Dress

A purple cotton midi shirt dress featuring soft flannel, herringbone texture, and a removable tie belt.
Women's Signature Camp Shirt Dress, Button-Front
Price was from: $119 now: $99.99

A breathable cotton shirt dress in faded olive vintage camo, featuring roll-tab sleeves and a removable belt.

Pros: Simple yet chic Timeless appeal Elegant Stylish design High-quality fabric
Women's Signature Castine Cotton Popover Dress
Price was from: $119 now: $99.99

A soft, blue cotton popover dress with a fit-and-flare silhouette and convenient side seam pockets.
Women's Signature Linen-Blend Dress
Price was from: $99 now: $44.99

A navy splitneck shift dress in a 55% linen, 45% rayon blend with side seam pockets.
Women's Signature Camp Flannel Shirt Dress, Button-Front
Price was from: $119 now: $99.99

A knee-length, slightly fitted shirt dress in royal red, made from 100% cotton flannel with chest pockets.

Holiday Midi Dresses

As the days grow shorter and a crispness settles in the air, the holiday season brings with it a special kind of excitement—one that has us looking forward to gatherings, celebrations, and those memorable moments spent with friends and family. Holiday midi dresses are a timeless choice for these occasions, offering a blend of comfort, style, and versatility that feels just right as fall transitions into winter. Whether you’re planning to host a cozy dinner at home, attend a festive office party, or enjoy a night out in town, a well-chosen midi dress can help you feel at ease while looking your best. The beauty of a midi dress lies in its ability to strike a balance: the length is flattering for all ages and body types, providing just enough coverage to keep you comfortable as temperatures dip, while still allowing for freedom of movement as you mingle, dance, or chase after little ones. Many people find that a midi dress quickly becomes a go-to in their holiday wardrobe, thanks to its effortless style and practical details—think easy-care fabrics, forgiving silhouettes, and thoughtful touches like pockets or adjustable waists.

When it comes to choosing a holiday midi dress, there are a few things worth considering to make sure you find one that fits seamlessly into your plans. Look for quality materials that hold up well through repeated wear and travel—whether you’re packing for a weekend away or simply moving from one celebration to the next. Soft knits, brushed cotton, and blended fabrics with a bit of stretch are all excellent choices for all-day comfort, and they layer beautifully with cardigans, tights, or boots as the weather cools. If you’re giving a midi dress as a gift, it’s a thoughtful option for anyone who appreciates versatile, easy-to-wear clothing that can be dressed up or down with a change of shoes or a favorite scarf. A holiday midi dress is a wonderful way to show someone you care, offering them the chance to feel special during a season that’s all about connection and joy. For those who love to add a personal touch, consider pairing a new dress with a handmade ornament or a handwritten note tucked in the box—small gestures that make the gift even more memorable.

Holiday midi dresses are also a practical solution for those busy days when you need an outfit that’s ready for anything, from a morning at the office to an evening spent around the table with loved ones. Their timeless appeal means they’ll look just as relevant next year as they do this season, and with so many styles, colors, and patterns to choose from, it’s easy to find something that suits your personal taste. Whether you gravitate toward classic plaids, rich jewel tones, or festive prints, you’ll find plenty of options to express your own sense of fun and celebration. And if you’re looking to expand your wardrobe beyond holiday gatherings, you can find even more inspiration in our collection of Cute Dresses, where comfort and versatility are always at the forefront. With the right midi dress in your closet, you’ll be ready to make the most of every occasion—big or small—that the holiday season brings your way.

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Holiday Midi Dresses