Holiday Dresses You Can Wear to Every Winter Event
The holiday season always seems to fly by fast, doesn’t it? Instead of buying a different outfit for every single thing, I love finding dresses that can work for the entire season. From Thanksgiving all the way through Christmas, I want something easy to wear that I can just do a quick change of shoes, jewelry, or a cardigan to change up the look. It saves money, saves time, and keeps getting dressed stress-free. Sign me up!
I’m sharing holiday dresses you can wear to every event on your schedule, plus simple styling ideas to help you get the most out of each one.

You can find this Amazon dress and more in this post: 3 Stunning Amazon Dresses I Tried for a Fall Wedding
Okay, this is not technically a dress, but I’m still including it since it’s not pants, either. This outfit is gorgeous, and so versatile since each item can be worn separately. To see more holiday pieces, check out this post: The Best Talbots Holiday Outfits for Every December Event.
Versatile Amazon Holiday Dresses for Every Event
This is one of those sweater dresses that just makes getting dressed easy! The wool blend keeps you warm, the tie waist gives your waist a little shape, and the pleated skirt gives it a little texture to hide any problem areas. Throw it on with boots, and you’re ready for anything from holiday errands to a casual get-together. It’s comfortable, it’s flattering, and it’s the kind of dress you’ll reach for over and over.
This dress is super soft and comfortable, which is exactly what I’m looking for when I’m getting dressed for a long day! The fabric has a nice weight to it, and the slight sheen makes it look a little fancier than your average dress!
If you’re wondering how to accessorize for a holiday party, read The Best Festive Dress Shoes For The Holidays and How to Add Sparkle to Your Holiday Outfits next.
This velvet maxi is such an easy pick for the holidays. The V-neck is flattering, the short sleeves keep it comfortable indoors, and the velvet gives it a seasonal look without going over the top. It works for Thanksgiving dinner, Christmas parties, and everything in between. Just change your shoes and jewelry, and you’re good to go.
This wrap-style midi is one of those dresses you can count on. The smocked waist makes it comfortable, and the long sleeves are great for cooler days. It’s easy to dress down with boots for Thanksgiving or dress up with heels for a Christmas get-together. Simple, flattering, and very wearable.
This plaid tunic dress looks similar to a much more expensive Tuckernuck dress! It’s relaxed, lightweight, and easy to throw on with boots or tights. The plaid pattern gives it a festive feel without being too much. Perfect for casual holiday gatherings, running errands, or hosting at home.
Talbots Holiday Dresses I’m Loving
If you love a cozy outfit for the holidays, this cable knit shift dress is a winner. It has a relaxed fit that’s comfortable for busy days but still looks put together. Wear it with tall boots or leggings for an easy, classic look.
This pleated merino wool dress is stunning! I love the deep red color, especially paired with a red lip. You could really add some fun accessories to make this one pop, like a sparkly necklace and earrings or a plaid shoe!
This mockneck shift dress is one of those easy pieces you can grab for just about anything during the holidays. Wear it with tights and boots for a simple, put-together outfit you don’t have to think twice about. It’s great for work, church, or any casual holiday plans!
More Holiday Dresses from Your Favorite Retailers
If you love a good plaid moment during the holidays, this tartan shirt-dress is so cute! Pair it with tights and boots for a casual holiday outing or throw on a cardigan if you need an extra layer. It’s festive AND comfortable!
This lace midi dress from Lands’ End is a great pick if you need something a little dressier for the holidays. The square neckline is flattering, and the pleated skirt gives it a soft, easy shape that moves well. It’s comfortable to wear and works for anything from Christmas services to a special dinner. Add heels if you want to dress it up, or keep it simple with flats.
This plaid maxi is such a fun piece for the holidays. The print makes it festive without looking costume-y. You can wear it with boots now and switch to flats or heels for December plans. It’s a simple, comfortable dress you can grab for all kinds of events.
If you’re traveling at all this season, this Travelers maxi dress is a lifesaver. The fabric is wrinkle-free, so it still looks good even after you’ve been in the car or on a plane. The boatneck keeps it classic, and the maxi length gives it a dressy feel without being fussy. Add a wrap or jacket, and you’re set for anything on your holiday schedule.
I love this velvet dress, gurls! The V-neck is flattering, the 3/4 sleeves give you a little coverage, and the fabric makes it feel seasonal without being over the top. It’s one of those dresses you can wear to church, dinner, or a holiday party with nothing more than a quick change of shoes. Comfortable, simple, and perfect for the busy weeks ahead!
If you don’t love wearing a dress, this velvet wrap jumpsuit is a great holiday option! It’s especially nice if it’s cold outside and you don’t want to fool with adding tights or pantyhose. Add heels if you want to dress it up, or wear simple flats for a more relaxed look.
Shopping for more jumpsuits? Head over to The Best Dressy Jumpsuits for Holiday Parties
Shop More Holiday Dresses for Women Over 50:
How to Pick a Dress You’ll Actually Wear More Than Once
A few things help a dress earn repeat wear:
- Sleeves (always handy for chilly weather)
- Comfortable fabrics
- A length that works with boots and heels
- A shape that’s forgiving at dinner
- A color that feels right in both November and December
If it checks these boxes, chances are you’ll reach for it more than once.
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Verse Of The Day

🙂 You look lovely in the BerryGo Velvet V Neck Wrap Fall Maxi Dress. I also really like the plaid skirt with the Christmas tree sweater.
😊 The sweater is so pretty. I like the red plaid if I was a blouse.
🙂 Awe Sweet Lucy! That’s funny! she comes out and takes your spot! I love the sweater dress the blue Velour dress!