Long dresses that women over 50 can wear all winter

Long dresses for women over 50 during the winter can be challenging. This post shows you where to buy them and how to style them to keep warm and stay stylish this season.

Photo courtesy of Modern Citizen

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love a good dress. It’s a 60-second outfit. Add shoes and jewelry then head out the door. I always feel feminine, pretty, and stylish when I’m wearing a dress. But can you still wear one in the winter? You can. It’s a matter of finding the right one. 

Winter aside, I work with women over 50 all the time who think that their days of wearing dresses are over. Wearing a dress over the age of 50, especially in the winter, comes down to the material, pattern, and cut. Longer dresses in heavier fabrics make for a cozy winter outfit. And wearing a dress over 50 is an excellent way to disguise some of the things we wish were a little different with our bodies. 

A longer winter dress can draw attention away from your midsection and cover your arms. These are the top two requests I receive when showing women what to wear. The three styles of dresses that I recommend women over 50 wear during winter:

  • Sweater dresses
  • Wrap dresses
  • Winter maxi dresses

Sweater dresses

A sweater dress is a great option to keep you warm in winter. There are plenty of different styles to choose from and you can do wool, cashmere, or whatever material works for you. I can’t wear wool right on my skin, so I usually opt for some kind of blend. A sweater dress does not have to be bulky or frumpy. An off-the-shoulder style makes the dress sexy. Buttons up the front make for a more casual and fun look. A turtleneck sweater dress is modern and sophisticated. 

Style tip: Pair your sweater dress with tall boots, tights with mary janes, or heels.

The off-the-shoulder number is sexy and cozy at the same time. You of course can wear it with both shoulders covered and a deeper v-neck or add a belt. There are a handful of ways to style this same dress to make it look like a completely different one. This also comes in a handful of colors. 

The button-up sweater dress with a collar is a casual style that you can wear with tennis shoes or boots. You can leave as many buttons undone to make it edgier or more conservative. You decide. Again, this one offers you flexibility.

The turtleneck option is cozy and warm but still sophisticated. Add in some boots and big gold earrings for a polished look for the office. 

Wrap dresses

A wrap dress is flattering to all body types and a great way to disguise any midlife tummy issues you may be experiencing. A wrap dress creates an hourglass shape with a v-shape at the neck and a cinch at the waist built into the garment. Some of these options tie up higher on the torso so that the fabric can flow over your midsection. 

Style tip: If you carry your weight in the middle, opt for a wrap dress that you tie just below your bust line.

The wrap dress in Shiitake is such a pretty winter white. It comes in a handful of colors but I love this all-off-white look. The wrap on this dress is great to hide your tummy and you can adjust it if you are between sizes. I have last year’s version of this and it’s soft and cozy. 

The deep burgundy plisse dress is not a traditional wrap dress. It does create the same cinch at the waist and a v-shape at the neck as a wrap dress. This one looks great on lots of different body types, and the color is gorgeous for the winter. You can wear this dress for holiday parties or a winter wedding. 

The ruffle-printed wrap dress is silk. It’s body type friendly because you can adjust where you tie at the waist. This means the dress can accommodate various body types. The print and the ruffle make this wrap dress stand out in your winter dress collection.

Winter Maxi-dress

I’m sure you’re familiar with the cotton flowy summer maxi dress, but what about a winter maxi dress? These are long-sleeved and made from heavier materials. They are also in darker patterns and colors to go with the season. And nothing could be easier to wear. Like their summer counterpart, these are flowy and not confining at all. You can wear these with tall or short boots, loafers, or dress them up with high-heeled sandals. 

If you’re petite, select a style that has a tie at the waist so it won’t overwhelm your frame. Or add a belt to highlight your shape. 

The lux shimmer material is stunning. Again beautiful for a winter wedding, New Year’s Eve celebration, or small at-home dinner party. This is more of a special occasion dress, but still practical enough to wear to dinner around town. 

If you like the shimmer effect but want a better deal, this brown metallic maxi dress is for you. It gives you the same fancy vibes as the lux dress but for less. The accessories and shoes change the feel of this dress, but I’d keep everything minimal and let this dress shine. This one also looks amazing on different body types.

This winter floral is so feminine and pretty. This can take you from school drop-off to a meeting at the office to dinner out. I would pair it with boots for work or sandals for a night out. 

This is a pretty play-on as a scarf-style dress. The contrasting patterns take care of pattern mixing for you. Which in my opinion always elevates an outfit. I’d wear this with tall brown boots and simple gold jewelry

Now go dig through your closet, see what long dresses for women over 50 you have in there that would be perfect for winter.



I show women over 50 how to get noticed, stay relevant, and be connected through their wardrobe. Getting dressed is something you have to do each day, why not make it fun.



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