How to Style a Sweater Dress Over 50

How to Style a Sweater Dress Over 50

After yesterdays post on sweater dresses, I made a mad dash to the mall to try some on. Many of you remember wearing sweater dresses in your 30’s and 40’s, but few wear them now. Most said they doubt they’d wear one again. I  think I know why.

Jennifer Connolly of A Well Styled Life wearing sweater dress from LoftAn online search for sweater dresses frequently brings up images of young, very thin women wearing tight, skimpy or clingy sweater dresses. I knew that was not how I wanted to look and dug deeper to find non-clingy ones that look stylish.Jennifer Connolly of A Well Styled Life styling a sweater dress

Case in point. This dress. It’s on sale and has lots of potential. The fabric is soft and warm with stretch built in so it doesn’t bag out. I wore it all day yesterday and loved how comfortable it is.

The following collage shows some styling options.

I think the wide suede belt looks too heavy for the dress but would work on a taller woman. The narrower belt works for my height but I would prefer it in suede. I’d also prefer suede knee boots to these leather ones.

Closed toe booties would obviously be better than my peep-toed ones. They are now on my keep an eye out for list.


The success of a sweater dress for women over 50 involves fit, silhouette and fabric. Clingy is seldom flattering so A-line or straight shifts are more likely to be flattering. Thin knits tend to show our lumps and bumps so look for fabric with some weight to it. A belt can change the entire look of the dress and add shaping without cling.Jennifer Connolly of A Well Styled Life styling a Sweater dress

My other sweater dresses are on their way and I hope they perform as well as this little inexpensive one.

Thanks for reading and have a great day!


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  1. January 7, 2018 / 5:33 am

    Thanks for the options you presented…I am certain this is very helpful for those who love sweater dresses!

    • Jennifer
      January 7, 2018 / 9:34 am

      Glad it might help!

  2. Linda
    January 7, 2018 / 5:34 am

    I am 66, work full time as a librarian and wear sweater dresses quite a bit. I have at least 5 in my closet. I am not skinny and certainly would never wear one that clings along every curve. One thing that is a must Jennifer is the proper undergarments. I wear a full slip always and occacsionally when of those full length spanx; for me what I found works best is that I bought 2 sizes up in the Spanx. It still holds me in but I can breathe! Plus it doesn’t crush my boobs!

    • Jennifer
      January 7, 2018 / 9:36 am

      I agree totally! I’m wearing a slip under mine. I always go up a size or two in slimming garments or they strangle me. I want smoothing not suffocating 🙂

  3. Laurel
    January 7, 2018 / 5:42 am

    Like the ways you’ve styled it! It’s sold out, but I would definitely try it on if I find it in the store.

    • Jennifer
      January 7, 2018 / 9:38 am

      Some stores may still have them but I knew they were selling out once the price dropped below $28.

  4. jodie filogomo
    January 7, 2018 / 6:13 am

    I love sweater dresses, but my only problem is when I wear tights with them, they cling. Do you wear a slip with yours??

    • Jennifer
      January 7, 2018 / 9:40 am

      Yup! I always wear a slip under skirts and dresses. Especially a sweater dress or you’re right, they cling like crazy. Especially to tights.

  5. January 7, 2018 / 7:04 am

    Thanks for the great posts. I just ordered the Pintuck Sweater Dress by Calvin Klein. Not super snug, I hope! Feeling a little thick in the waistline after indulging in too many Christmas Cookies.

    • Jennifer
      January 7, 2018 / 9:43 am

      I’m right there with you Gina! Way too many goodies and not enough water:) I hope it works for you. Remember a slip!

      • January 7, 2018 / 11:09 am

        I haven’t worn a slip in 35 years! I’m 56. Guess I have a lot to learn. Thanks!

        • Jennifer
          January 7, 2018 / 11:51 am

          Visit the lingerie department Gina. Slips have come a long way!

  6. January 7, 2018 / 7:18 am

    I like that on YOU!For me I would need it to HIT the GROUND!

    • Jennifer
      January 7, 2018 / 9:45 am

      They do make full length ones but not often. I imagine it would be pretty warm!

  7. January 7, 2018 / 9:26 am

    Good color and cute sweater dress. I think I like it best without the belt.

  8. Linda
    January 7, 2018 / 9:52 am

    You made great points here and I love the dress on you. Can understand why you might want a thinner belt, but the wide belt looks good on you in the photo. Also, good discussion on undergarments, etc. Really helps women “of a certain age” figure out how to dress stylishly.

    • Jennifer
      January 7, 2018 / 11:48 am

      Slips are helpful for many reasons, not just modesty. I love them Linda!

  9. Tasi Zuriack
    January 7, 2018 / 10:05 pm

    Hi Jennifer. Loved this post so much that I included it in my most recent article on The Sweater Dress…A Winter Delight And for you ladies asking about slips, the slip extender is a wonderful way to make a fashion statement with a sweater dress

    • Jennifer
      January 8, 2018 / 8:57 am

      I’m so glad you enjoyed it! Sweater dresses are a great option!

  10. January 8, 2018 / 11:13 am

    My bestie and I were consignment shopping after my birthday lunch last year, and found a beautiful charcoal grey Ann Taylor sweater dress in just my size, which she bought for me! I love it! I has a cowl neckline that dips a bit in the front – very feminine and dare I say, sexy! I wear a Spanx slip underneath and like wearing it with opaque tights and flats toned to the color of the tights, or with tall black boots. I’ve not tried wearing it with booties, but am intrigued! Although I’m not as tall as I used to be (5’7-1/2″ vs. 5’10”), I still think of myself as tall, so proportion shouldn’t be a big problem. When I belt the dress, I do so with a thinner belt rather than a thick belt, which I think “scrunches” the dress and emphasizes my abdomen and backside (not in a good way!).

    • Jennifer
      January 8, 2018 / 11:51 am

      Your dress sounds gorgeous! Great find Candy. You are tall in my book:) I love the sound of your outfit. Matching the shoes to your tights does lengthen the leg.

  11. January 8, 2018 / 2:02 pm

    I love the colour and the silhouette. I much prefer it unbelted. Like many of your readers, I haven’t worn a sweater dress in years, but after reading your posts and seeing these photos, I might reconsider!

    • Jennifer
      January 8, 2018 / 7:43 pm

      Me too Elaine. It was the comfiest without the belt too!

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