Our Medium Length Sweaters Over a Dress

Making Sweaters Modern for any age group.

Sweaters for Any Ages: The Medium Length Ones

Quote of the day: “Why is a windshield so large and the rearview mirror so small? So we can look ahead and move on.” Cheri Acosta

The calendar may say February, and many of us are wishing for warmer weather. But the truth is, it can still be quite cold outside. So I figured the sweater theme would still be appropriate for the majority of us.

I’m not sure if there is another name for this length of sweater, so I’m calling them the medium length ones. Since I covered the longer ones in the last post, here, and we will style short ones next; I figured these are the ones in between those two.

To me, this length can be tricky to style, at least for me because I’m so short. Sometimes, I feel like this length can cut me off in a strange place. They tend to be more voluminous at the bottom hem, but not always long enough to wear with leggings. In order to counteract these issues, I layered them over our dresses! It reminds me of the time we styled a dress 3 ways, and this method makes your dress into a skirt!

Tell me how do you wear yours in the comments below?

Jodie’s (50’s) Outfit: I recently purchased this sweater thinking I could wear it with leggings. Of course, when I tried it on at the store, I was wearing jeans. Consequently, when I got home and experimented, it seemed too short for leggings!

Making Sweaters Modern for any age group.

Luckily I really liked the sweater either way. I think the zippers on the side make it more fun than my other sweaters! Besides, it worked great layered over this print dress! I went a little crazy at The Limited’s close out sale. This dress was just one of the items I bought!! And it was only $30!

Making Sweaters Modern for any age group.

Most of the time, I want my accessories to really stand out. But, for this peacock pin, I really thought it was nicer that it blended in more, yet was functional by using it to hold the scarf together!

Making Sweaters Modern for any age group.

I don’t have navy boots to have worn with this outfit, and I thought the black ones would be a little too dark, so I threw on my grey boots. I end up wearing these quite a bit with dresses and I know, you’ve seen them a lot. But that is real life, in that we wear our items over and over, right?

Making Sweaters Modern for any age group.

Dress: The Limited (similar here in a paisley)~~Sweater: Cabi-thrifted (similar here or here an even better deal)~~Boots: Payless (similar here)~~Scarf: (similar here)~~Brooch: (similar here not as colorful)~~Earrings: (similar here)

Nancy’s (60’s) Outfit:  For Nancy’s longish, but not super long sweater, I picked her leopard print one! This sweater is a little longer in the back than the front which can be super flattering. Especially if you’re trying to cover the rear!

Making Sweaters Modern for any age group.

Nancy always refers to this dress as her “butt hugging dress” which cracks me up! The dress is more form fitting than most of her other ones, but I always think it’s nice to have variety in our closets!! And it certainly isn’t too tight. I think the ruching aspect, that is part of the design makes it very forgiving (not that her body needs forgiving—I’m just sayin’)!

Making Sweaters Modern for any age group.

Since the dress has a red, purple tone to it, we added in her burgundy necklace & earrings. Considering the shoes are nude & black, I figure they go with everything. And yes, if you’re wondering, Nancy’s wearing hose!

Making Sweaters Modern for any age group.

 To give you an idea of how this sweater looks with jeans, you can see Nancy wearing it with her lace extender, here.

Making Sweaters Modern for any age group.

Dress: Pure & Simple (similar here solid color or here in a print)~~Sweater: LOFT (similar here)~~Shoes: Anne Klein (similar here in a pump version or here all beige)~~Necklace: (similar here with more gold and under $5 or here with a pendant design)~~Earrings: (similar here)

Charlotte’s (70’s) Outfit: My mom wore this same sweater in our leather skirt post, here! For today’s outfit, I had her wear it over her black, maxi dress. We call it a maxi dress, but it really isn’t super long on mom. But you can see this exact same dress worn on Nancy in our maxi dress series, here–and it’s longer on Nancy!!

Making Sweaters Modern for any age group.

The black maxi dress is a turtleneck, but it’s short sleeved, so mom wore a black, long sleeve shirt under it. Then by wearing the black tights and ankle boots, it really puts the focal point on the sweater!

Making Sweaters Modern for any age group.

Since my mom has a ton of turquoise jewelry, I had her pile it on to bring out that same color from the stripes in the sweater.

Making Sweaters Modern for any age group.

One of the ways that this strikes me as more modern, is the fact that mom is wearing ankle boots with it instead of tall boots! I know many women don’t like the idea of cutting of the length of their leg with ankle boots. But I really think by matching them to the tights, you still get that long, vertical line!

Making Sweaters Modern for any age group.

Dress: K Studio (similar here with a v-neck)~~Sweater: Style & Co (similar here)~~Boots: Bandolino (here or similar here)~~Earrings: (similar here)~~Bracelet: (similar here and here)~~Rings: (similar here, here, & here)

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Charlotte’s photography by Kari Strand Photography

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Here’s some more in this length:

  • Bernadette Laganella

    I have been tempted to do this many times and your post is just impetus I need. Thanks for your support of the Senior Salon.

    • Jodie Filogomo

      It’s funny how it’s not really that different than throwing a cardigan over them—yet it seems so unusual!!
      Thanks Bernadette!!

  • JoAnne Price

    Jodie, I love your sweater, scarf and the broach! Your Mom has amazing turquoise and pairs it well with her outfits! Keep up the good work! You look like you are having fun🤗

    • Jodie Filogomo

      Thanks JoAnne!! There’s probably a ton of turquoise in Phoenix, huh? You may even have your own collection?
      Thanks so much for saying “hi”—I hope your starting to mend and feel better??

  • I like your sweater with the zipper detail. I like tops that go longer at the back than the front.

    • Jodie Filogomo

      Thanks Leanne!! It definitely was calling my name, because, sure I could knit a sweater, but I’m not sure I could add that zipper detail myself!!

  • I’m very / quite overweight so it’d decades since I’ve tucked anything in so I only wear longer shirts and longer sweaters. I love the look of a longer sweater with something fitting underneath – skirt, dress, trousers – particularly if you’re already bulky like me! #teamlovinlife

    • Jodie Filogomo

      I hear what you’re saying Deborah!!
      Thanks for stopping by!

  • Great as always and I really love your dress Jodie! Have a great day.

    Gemma x

    • Jodie Filogomo

      Thanks Gemma!!

  • All of your sweaters are lovely! I have always wanted to try wearing a sweater over a dress like this. I will have to give it a try once it cools down! And oh wow – everyone’s shoes and boots are adorable too. And oh my gosh – Nancy’s “butt hugging dress” too funny! Loved her description. 🙂


    • Jodie Filogomo

      Thanks Lindsey!!
      I know when Nancy told me she called her dress that—I really did laugh out loud!! But she’s not used to form fitting clothing (before this) so it was a different experience for her!!
      Thanks for the love!!

  • I love your stylish outfits Jodie, especially yours with the pink scarf 🙂 #TeamLovinLife

    • Jodie Filogomo

      Thanks so much Lyndall!!

  • writeofthemiddle

    You three always look so stylish! I’ve never thought to wear a sweater over a dress but then that might be because where I live it rarely gets cold enough to wear a sweater! Remember I said that I was not really a broach girl – well I think I might need to eat my words because I absolutely adore the ‘peacock pin’ (is that a broach or something different) on your scarf! 🙂 #TeamLovinLife

    • Jodie Filogomo

      Well, I’m a little jealous, Min that you don’t get cold weather!! Although I might go into withdrawals if I wasn’t able to knit sweaters anymore because it was too warm! Ha ha!! (you can see 3 different sweaters I knitted myself on the blog today even!!)
      And how cute that you liked this brooch! I think it’s quite a statement piece, and maybe you think of “brooches” as more grandmotherly?? Who knows, but I’m glad you like it!!
      Thanks for stopping by!!

  • I love the first two as well – and to tell you the truth I’ve never thought about wearing a sweater over a dress! Don’t ask me why not! But why not indeed? It makes perfect sense and adds another new outfit to your wardrobe. #teamlovinlife

    • Jodie Filogomo

      That’s exactly how I felt when I first saw another blogger wear a sweater over a dress a couple years ago—it was like the V-8 commercial, ha ha!!
      Thanks for stopping by Johanna!!

  • Kathy Marris

    I love these sweaters, particularly the first two. I find some sweaters are far too long for my short height and are not flattering. Nancy’s ruched skirt is very stylish – I love the colour. 🙂 #TeamLovinLife

    • Jodie Filogomo

      I’m short too, so I totally get that. I wonder if I should add my dress lace extender under this length to make it more of a dress or tunic?
      Thanks for stopping by Kathy!!

  • I do think sweaters this length can be a little trickier, but you all look really great in them! I love how these turn your dresses into skirts and you get more wear out of everything.

    Amy Ann
    Straight A Style

    • Jodie Filogomo

      Thanks Amy!

  • Love all these beautiful looks! Nancy’s skirt has caught my eye. The ruched sides and color are so chic! I’m also in love with all your mom’s turquoise jewelry. It really makes her look pop.


    • Jodie Filogomo

      Thanks so much Kathrine!! Mom & Nancy will love reading your comments–it always makes their day!!

  • Judy Gramith

    I really like the idea of extending the wear of both dresses and sweaters by combining them in this way. I rarely have a need to wear a dress since I retired five years ago and now if I wear them at all its a summer look.
    I really like the print of your dress and I think your gray boots were a good choice here! Nancy’s gray animal print sweater combined with the dark cherry of her dress is also nice. I think I would prefer a gray shoe /boot though. Charlotte looks so pretty dripping in all of the turquoise jewelry. I think turquoise is a universally flattering color but looks so pretty with Charlotte’s white hair.

    • Jodie Filogomo

      I totally know what you mean about wearing dresses now, Jude! I think I end up wearing them more lately just because I have them and not as many other women wear them!! Besides, what kind of fashion blogger would I be if I only wore jeans?? Ha ha!!
      Thanks for the lovely words too for mom & Nancy. They always love to read these comments!!

  • Haha Nancys dress! She looks fabulous though. And I love your zipper details on that sweater. And I love the collection of your Moms jewelry!


    • Jodie Filogomo

      Thanks so much Ruth!!
      I do love Nancy in this dress—it’s so different than what she normally wears!!

  • I like seeing the same items repeated, for what it’s worth, Jodie. Most of us don’t have the unlimited closet space to allow us to wear things only once a season, even if we could justify the cost (and shopping time). Your posts always give me ideas for new ways to combine some of my old faithfuls (not that it really matters all THAT much, since I work from home and hardly anybody ever sees me) 🙂 I am still a “girl” at heart, however.

    This mid-length top is especially awkward for those of us who are tall, too, btw. Seems to put the focus on an area of the body *most* of us would rather not have the eye drawn toward, if you get my drift. Most of my sweaters are long enough to wear with leggings – concerned with covering the front more than the back. The ones I wear most often have POCKETS! (They would all be dress length on you, however.)

    I rarely wear ankle boots except with pants – since I no longer stock
    stockings and tights since I moved to leggings, and I hate the look of
    the “gap” (long legs) — but I’m lusting after your Mom’s turquoise jewelry!

    (Madelyn Griffith-Haynie – ADDandSoMuchMORE dot com)
    ADD Coach Training Field founder; ADD Coaching co-founder
    “It takes a village to transform a world!”

    • Jodie Filogomo

      Well, it is true that most of us have to wear items over and over! But even if I had the money, I think I’d feel wasteful not enjoying these items that I love, more!! I guess it goes to show that I’m truly a clothes person—I love looking at them, and fingering them, and imagining how I’m going to create an outfit with them!!
      My mom probably could wear something different every day and not repeat an item—including her jewelry!!
      I did have to laugh at the fact that you included pockets for your sweaters!! I read all the time, that women love them. I must be a strange bird to say that they don’t float my boat the way they do for others. Maybe it’s because I grew up with a mother who always would cut them out of dresses and such to decrease the bulk!?? You can analyze that one…ha ha!!
      Thanks for your voice on this —it’s so fun to hear different perspectives!

  • Love all of these outfits, especially yours! The navy and pink work so well together and I love that you’ve added a print.


    • Jodie Filogomo

      Thanks Liz!!

  • Kirsten Wick

    I think your sweater works fine with the skirt, especially because your skirt is a pencil one and the sweater not too wide, it still gives you shape. Love, Kirsten x


    • Jodie Filogomo

      Right Kirsten….that’s so true about the shape. This length wouldn’t work with some flared skirt dresses!! I should have added that!!
      Thanks for stopping by!!

  • Mireille

    I love, love your outfit!

    • Jodie Filogomo

      Thanks so much Mireille!!

  • I like that you all are wearing grey! I look forward to seeing the whole dress you have one as the print is pretty Jodie and love the peacock pin! Both your mom and Nancy look great with a longer sweater over the dresses and they look cozy too!
    jess xx

    • Jodie Filogomo

      Thanks Jess!!
      I just loved the colors in this dress! And it’s long sleeved which seems so rare lately!! I’ll try to wear it soon so you can see it in full!!

  • Tina von tinaspinkfriday

    It is cold outside. This is the perfekt way to wear dresses in winter. Great pictures!
    xoxo Tina

    • Jodie Filogomo

      Thanks Tina!!

  • Queen of Rods

    All three outfits are winners today…I like your mom’s booties with the tights and longer skirt. But I especially like your outfit and accessories today, Jodie…particularly your pink glasses!

    • Jodie Filogomo

      Thanks Janet!!
      These are my new “progressive” glasses! I just got them from the eye doctor’s office. Of course now I need a couple more pair for variety!!

  • I never know exactly how to wear this lenght! I always buy shorter and then think:mm, this is to short!😂😂😂 Perhaps I never wore it on a skirt because I have to add more accesories! Or a scarf!

    • Jodie Filogomo

      I think we get used to a certain length too, Nancy. Then when we get a different one, we don’t know what to do!!

  • Stevie Turner

    I love the long hip-length jumpers – they go well with leggings and they’re quite flattering to the figure too.

    • Jodie Filogomo

      Thanks Stevie!!

  • I love sweaters. Unfortunately, living in TX, we don’t get to enjoy them very long. 🙂 I also LOVE that peacock pin. What a find!

    • Jodie Filogomo

      Ha—no fair bragging about the lack of cold weather!!! 🙂
      But your point is quite valid. Since I am an avid knitter, I’m not sure I could live where I don’t get to wear all of my sweaters!!
      But I’m sure I’d manage…ha ha!
      Thanks for stopping by!
      Can you believe I bought that peacock pin in the Vegas airport—for $13? I do love my accessories!!

      • Wow! That is an awesome deal! Maybe I should pay more attention to the airport shops the next time I fly. 😉

        Oh, I’m not bragging. I prefer the cold weather. LOL I love TX but wish we had cooler weather. 😉

  • Karen

    Love all these looks. Your mom is one of the classiest dressers I’ve ever seen. Each post just inspires me with her style. I also sew some of my clothes, and she is very talented and makes beautiful things. I do like all of the styles shown here, and am now inspired to try some sweaters over my dresses!

    • Jodie Filogomo

      Oh, Karen. What a wonderful comment to read and my mom will revel in your words—so thank you for that!
      It is an easy look to recreate, and it always amazes me that I never thought of doing this until I saw another blogger style it!!
      Thanks for joining in!

  • You did it again!
    When I first skimmed your post, I thought “that’s a cute skirt”…. Hmmm, you actually get extra duty out of your dresses…very clever!!! Skirts can be tricky for me for a couple of reasons (mostly they never stay put)…but the dress lays so nicely. Definitely going to try this pairing 🙂

    • Jodie Filogomo

      It’s funny because it doesn’t seem like rocket science, right, Em? But I remember when I first say a blogger do this and it was like a V-8 moment!! Of course I’ve layered cardigans over a dress to keep warm, but how was it I never thought to use a normal sweater?
      But now that I’ve done it a couple of times, it seems so easy & fun!! And you’re right—it could be better functionally since a dress is one piece!!
      Thanks for the love—I really appreciate it!

  • Versatilestylebytracey

    I love the idea of wearing longer sweaters over a dress. DD wore a long sweater over a skirt that she wants to redo from it;s bubble shape to an
    A-line. It was her Valentine;s look and made the skirt shape wearable, lol

    • Jodie Filogomo

      What a fantastic item to change the shape that way!!
      Thanks for the idea, Tracey!!