The Best Holiday Dresses for Women Over 50

Whether you’re gearing up for a family gathering, a fancy holiday dinner, or a special Christmas church service, finding the perfect dress as women over 50 shouldn’t feel like a chore. I’ve rounded up some fabulous options from brands we know and love, such as Talbots, Chico’s, J.Crew Factory, Amazon, and more. These holiday dresses are stylish and age-appropriate (but never dull!) and will have you feeling confident no matter what’s on your calendar this winter!

Okay, this technically isn’t a holiday dress, but it still gives the same vibe. There are times I like a “one and done” look, and other times I want the versatility of two pieces. It’s up to you to decide which works best for you, and you can’t go wrong either way.

The Best Holiday Dresses for Women Over 50

Holiday Dresses from Nordstrom

This velvet fit-and-flare dress has just the right amount of holiday drama with its twist-front detail and rich, luxurious fabric. This is totally dressy enough for cocktail attire or a holiday wedding! Just add some sparkly jewelry and a metallic clutch.

This sweater dress just screams class, and it has the perfect amount of sparkle. P.S. If you don’t love showing this much leg, just add a pair of tights and a knee-high boot!

Holiday Dresses from Talbots

Talbots always knock the holidays out of the park! This velvet shift dress looks warm and cozy if it’s cold where you live. Pair it with heels, ballet flats, or a bootie, depending on where you’re heading!

A cozy sweater dress is like wearing your favorite sweater in dress form. This turtleneck one can easily serve double duty since you can wear it to the office, too! Dress it up with heeled booties, or keep it casual with knee-high boots.

There’s something so fresh and unexpected about wearing blue during the holiday season—it feels elegant and wintery without being too traditional. I think the color of this dress will look so pretty with silver, so add a silver shoe or clutch with some statement jewelry to complete the look!

Holiday Dresses from Chico’s

I told you gurls in this post that feathers were on the rise this season! The sleeves on this dress add a playful and glamorous touch without going over the top. Pair it with simple heels and let the feathers do all the talking.

Oh, I love the texture that lace brings to the table! You could wear this maxi dress just like this, or you could add a belt to define your waist. Either way, it’s a show-stopper!

Heading somewhere a little fancier this season? You have to check out this metallic maxi dress! It’s the perfect mix of blush pink and metallic gold. Add some gold heels or ballet flats, and you’re ready to head to a winter wedding or a fancy holiday gala!

Holiday Dresses from Dillard’s

This tweed sweater dress from Lilly Pulitzer features a subtle metallic touch that adds just the right amount of glam. It’s the perfect combo of polished and festive, especially in this pretty green!

I know a lot of women don’t love buying something you can only wear once per year. You’re in luck, because this midi dress is the kind of dress you can actually wear all year long! Wear it in the fall or winter with heels, ballet flats, or booties, and then wear it again in the spring or summer with a sandal!

If you’re traveling to your holiday plans this year, this dress has your back! It’s made from wrinkle-free fabric, which means it’s not going to be a rumpled mess when you reach your destination. I love it paired with the black knee-high boots, but it would be just as cute with a black flat or loafer.

Holiday Dresses from J.Crew Factory

Nothing screams the holidays like plaid, and this puff-sleeve tartan dress is holiday perfection. It even has jeweled buttons, adding just the right touch of sparkle. It’s a charming option for family photos or a cozy Christmas dinner!

This ribbed mini sweater-dress is effortlessly chic and so versatile. Add tights and ankle boots for a casual day out, or dress it up with statement jewelry and heels for a holiday party.

Here’s another plaid option I found and loved! This one is sleeveless, so you might want to add a cardigan to give you a little extra warmth. I noticed they have the same print for the rest of the family, if you are a fan of matching with your crew (including the dog!).

Holiday Dresses from Amazon

If you’re a fan of longer-length dresses, this velvet dress is a great option for you! It’s almost floor length, so there’s no need for pantyhose (or shaving your legs, LOL!). It comes in a ton of other great colors, like burgundy and dark green!

Who says holiday dresses have to be red or green? I love the simplicity of this cream colored dress, and you can always add in a plaid headband or a red lip or heel if you want to look festive!

This one is giving me major Tuckernuck vibes, especially since it looks so similar to their Royal Stewart Tartan Palmerston dress! $34 vs. $228? I think so! I’d pair it with a classy flat or a closed-toe heel.

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Verse Of The Day

1 John 1:6 (NIV)
⁶ If we claim to have fellowship with him and yet walk in the darkness, we lie and do not live out the truth.