The Best Winter Dresses for Women Over 50

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I don’t know how things are in your neck of the woods, but in my neighborhood, it is getting COLD. If you’re like me, you’re spending a lot of time these days in leggings and loungewear. Occasionally, however, Joe and I shake off the cobwebs and hit the town for dinner. I want to look nice, but I don’t want to spend the evening shivering. Today, I’m sharing the best winter dresses for women over 50. Let’s get dressed up!

The Best Winter Dresses for Women Over 50 – From Nordstrom

I think this is so cute! I’d wear this with a belt, tights, and a great pair of ankle boots. Short sweater dresses are really trending right now, and I’m all about wearing what makes you happy. In the winter, longer dresses make me happy, so this midi sweater dress would be perfect for me. Lol!

Talk about cozy! This looks like loungewear in a dress. You could wear it in a very casual way and pair it with sneakers, or dress it up with heeled boots. I love the v-neck and wide collar. Did you see the two-tone cuffs? It’s a small detail, but you know how I love details! Remove the belt if you want, and add a vest for a different look.

Wool and cashmere? Yes, please! Who doesn’t love a dress that’s warm AND soft?! Sweater dresses don’t have to be tight-fitting. This relaxed-fit dress is gorgeous. Like the others, you can dress it up or down, as the occasion requires. I think this color is beautiful, but it also comes in black and camel.

The Best Winter Dresses for Women Over 50 – From JJill

Date nights aren’t always somewhere fancy. We love to go to a local sports bar to watch football games and have some wings. Go, team! lol. I’d also wear this to run errands or do some shopping. It’s all about being fashionable, comfortable, and warm!

How cute would this be with black boots? I love that it’s available in regular sizes up to 4x as well as petite and tall. The Wearever line is wonderful since you can travel in comfort and arrive without being a wrinkled mess. I love the geometric print, and the eggplant is a gorgeous color, but it also comes in solid black, which is a classic. Dress it up or wear it casually. Either way, it’s a winner!

Here’s a dress you can wear every day. It’s fitted around the shoulders but a bit roomier in the midsection. The V-neck is flattering on pretty much everyone, and it has large slanted pockets, my favorite! Chic, yet relaxed, it’s a great dress in a stretchable fabric.

The Best Winter Dresses for Women Over 50 – From Amazon

I love this casual, long-sleeved dress. The waffle fabric is perfect for those in warmer areas of the country. It comes in 15 different colors, and I love the button placket so you can unbutton it to the perfect V-neck. Runs true to size.

Sweater dresses are a great choice for warmth, but again, they don’t have to be body-hugging. This is fitted at the top, but flares at the skirt. It comes in 12 different colors, and you can replace the belt with something wider if you prefer. A statement necklace would be the perfect touch. Wear it with tights for added coverage and warmth.

I can’t get enough of these sleeves! The whole dress is just so elegant. Pleats are having a moment, and I am here for it. Between those sleeves, a great neckline, and the pleats, this dress would get a ton of wear. Also available in black.

I’m all for loungewear, but don’t forget that dressing up now and then can lift your mood. Let me know which of these dresses you like best!

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14 Comments

  1. I love sweater dresses! The Faherty dress is gorgeous.

  2. Really pretty sweater dresses!

  3. sue koren says:

    Love all of these looks!

  4. Debbie Brown says:

    I love the sweater dresses.
    You can dress them up or do a more causal look.

  5. Love the white pleated dress! Your wreaths look great!

  6. I love sweater dresses that aren’t body con. I just hope it gets cold enough to wear mine this year.

  7. Great sweater dresses for the holidays

  8. Love your wreaths on your windows!

  9. LOVE the burgundy A-line swing dress. Being only 5′ and a little “fluffy”, I can’t wear the long straight dresses. It makes me look like I am wearing my bathrobe.

    1. Lol! I’m still in my robe this morning, so there’s nothing wrong with that. Hahaha!

  10. Love these dresses! I love that black one from Amazon. I’m gonna order that one!!
    Love the wreaths on the windows too!

  11. Well, I agree about those sleeves and pleats. The last one is my favorite! I also like the one from JJill with the hood. I feel like that is one I would wear a lot.

  12. The sweater dresses are beautiful!

  13. Beautiful dresses, love your hair!