22 Must-Have Cute Holiday Dresses (& Skirts!)

It’s official, the most wonderful time of the year has arrived and we’ve curated a list of our favorite cute holiday dresses that’ll carry you from festive office get-togethers to long-overdue reunions with family. 

“This year, we are all ready to get back to what brings us joy,” said Wantable Buyer, Holly Norman. “That could be a sparkling, show-stopping dress or a more cozy chic look. Our stylists are excited to help you find cute holiday dresses that are perfect for you!” 

Stylists’ Favorite Cute Holiday Dresses

1. Pretty in Plum Dresses
2. Cute Holiday Dresses with Luxe Textures
3. Winter Floral Dresses
4. Comfy & Casual Holiday Dresses
5. Marvelous Midi Skirts
6. Shimmery Statement Holiday Dresses & Skirts
7. Little Black Cute Holiday Dresses

Pretty in Plum Dresses

Is there a more versatile color than plum? It’s certainly unbeatable during the holiday season. Show off your chic, feminine side in these eye-catching must-have cute holiday dresses.

1. Grade & Gather Unbalanced Skirt Maxi Dress

Comfort meets elegance in this alluring dress. Featuring an uneven hemline, flutter sleeves and a shirred waist, this versatile maxi works with ankle boots or plum square-toed mules. 

2. Hayden Los Angeles Textured Velvet Wide-leg Jumpsuit

This luxe velvet jumpsuit is a no-brainer for special occasions. Do you hear the wide legs calling for your favorite strappy heels? For a trendier finish, reach for simple white sneakers.  

3. Gentle Fawn Sonia Dress

This chocolate midi hits all the right notes with a flirty cowl neckline and convenient adjustable straps. Pair with dainty gold jewelry and heeled sandals for the easiest date night look that guarantees a smooch under the mistletoe.

Cute Holiday Dresses with Luxe Textures

Texture adds interest & dimension to any garment and the velvet and knit textures in these cute holiday dresses certainly master the balance between luxe and comfort! 

4. Adyson Parker Long Sleeve Velvet Dress

This is one of customers’ favorite cute holiday dresses for its flattering shirred waist and convenient side pockets. Rock it at holiday gatherings with beige booties or get a little trendy with classic doc martens! 

5. Gentle Fawn Monroe Dress in Cream

Experiment with layers and accessories in this versatile sweater dress. A leather jacket and tall, block-heeled boots will give it some edge or rock it with a wide-brim hat and brown suede booties and you’re ready for fall family photos!

6. Grace & Mila Dame Dress 

You’ll want a chic updo to show off the v-back on this charming knit dress. A beige dress like this is begging for color-coordinated accessories; black or rusty orange would be great for fall! Then swap in silver or gold pieces for the holidays. 

Winter Floral Dresses

Floral is always in season and we’re certain you’ll be reaching for these flirty, feminine dresses all year long. 

7. Lost + Wander Madeline Mini Dress

We absolutely adore the black trim detail on the neckline and wrists of this dress. It gives the otherwise flowy silhouette a bit of tailored finish. Pair with pink or golden yellow shoes to bring out the sweet floral print! 

8. Sadie & Sage Marigold Of Eventide Midi Dress

This midi dress features a deeper v-neck and modest side thigh slits; you know how much we love a peek-a-boo thigh moment. Layer with a denim jacket and finish with ankle boots or sneakers! 

9. Hayden Los Angeles Square Neck Puff Sleeve Belted Dress

If cute holiday dresses with a dose of personality are your thing, look no further. The square neck floral dress takes it up a notch, framing the collarbone perfectly. You’ll especially love the belted waist and the flattering cinch it creates. 

10. Hayden Los Angeles Long Sleeve Smocked Bodice Midi Dress

Reach for cream or beige shoes to lighten up this black, flowy holiday dress. An olive bag and dainty necklace would be the perfect finish!  

Comfy & Casual Holiday Dresses

A casual dress is always the answer when you’re looking for comfort and convenience. Lucky for you, we’ve brought in some best sellers from our favorite brands. 

11. Cotton Bleu Cotton Gauze Tiered Dress

With a looser fit this relaxed weekender dress is the essence of laid back. Layer with a denim jacket, your favorite scarf, and classic checkered Vans to add a little more interest! 

12. Velvet Heart Sherin Dress in Rust

Not only does this a-line swing dress feature the ultimate autumn rusty orange, it’s also made from a smooth corduroy that’ll keep you comfortable from day to night. You’ll love this with taller brown cowboy boots. 

13. BB Dakota Park City Dress

When you get an invite on short notice, go with a comfortable on-trend solution like this striped camel bodycon. It’s the ultimate ode to fall with its rust and gold hues and pairs perfectly with knee-high chocolate brown boots! 

Marvelous Midi Skirts

We have a very important update to share. The midi-length skirt is officially “in!” If 2020 put you in style rut, these super versatile cute holiday-ready options are here to revive you.

Cute holiday dresses, scooch over. It’s time to shine the spotlight on some of our  favorite skirts of the season. 

14. Wishlist Pleated Midi Skirt in Cream Combo

We’re here to debunk the myth that midis are only for the tall; just style with shoes of the same color to add the illusion of height! Layer a denim jacket over a graphic tee, tuck her in, and finish with platform cream sneakers. Voila!

15. Wishlist Pleated Maxi Skirt in Rust Combo

Rock this Rust version of the pleated maxi with a cream bodysuit; layer with an open-front soft blazer and finish with dainty black heels for a cute holiday-party-ready look!  

16. Lucca Couture Ribbed Sweater Skirt in Ivory

Since midis like this have fuller coverage, tuck in your top for waist definition! A dressier plaid top would be an especially great option for the season.

Shimmery Statements Dresses & Skirt

Complete your closet with these shimmery statement pieces that give holiday fashion a whole new meaning. 

17. Skies Are Blue Pleated Midi Skirt in Mauve

Mauve and navy make such a lovely combo, so tuck a navy elbow-sleeve modal into this flowy, romantic skirt, and finish with tall modest-heeled boots. 

18. Hayden Los Angeles Square Neck Belted Metallic Knit Dress

A dress this stunning and universally flattering doesn’t need a lot of help so just pair with simple heeled sandals and you’re ready for that company holiday party!

19. Hayden Los Angeles Trumpet Sleeve Dress

Show ‘em how it’s done in this one-of-a-kind metallic luxe mini. The dramatic trumpet sleeve balances out the arms and creates a super flattering shape! You’ll definitely leave a lasting impression in this one. 

20. Traffic People Lily Dress

Confession – this one may or may not have already made its way to my wardrobe. 😉 The high neck and black and gold print gives major retro vibes and I’m absolutely in love with the full puff sleeve and belted waist – so effortlessly flattering! Pair with white go-go boots or a shorter bootie to complete the full fantasy.

LBCHD – Little Black Cute Holiday Dresses

A little black dress is a no-brainer for your closet; it’s every woman’s go-to for occasions grand and small! These cute holiday dresses are staples that will carry you through the holiday season, whether it’s brunch with the girls or dinner with the family. 

21. Sadie & Sage Just Irresistible Midi Dress

This hypnotizing black bodycon dress is as comfortable as it is irresistible. Fitted to perfection, the belted waist and side-thigh-slit will have you ready for any occasion that the holidays call for!

22. Adyson Parker Sheer Sleeve Midi Dress

This fit & flare black dress is truly for everyone. The on-trend sheer sleeves and black rainbow print take this midi up a notch from your average black dress – especially if paired with stilettos. 

With the holidays, also comes peak party season and with these playful, one-of-a-kind cute holiday dresses, you’ll be sure to show up beaming with confidence and ready to cut a rug! 

So are you ready to turn heads? Get access to all these cute holiday dresses by signing up for your personalized Style Edit!