How Silly to Wear Jeans with your T-Shirt Dress

Styling our T-Shirt Dresses for the Colder Months.

The T-Shirt Dress for Any Ages: Paired with Jeans

Quote of the day: “Knowledge is being aware of what you can do. Wisdom is knowing when not to do it.” Anonymous

My original thought for the last category in making our t-shirt dresses work for the cooler months was to pair them with leggings. The problem I discovered was that the knit material of the dress kept clinging to the knit leggings. And having to wear a slip under it just seemed like too much work.

Then I saw in the March edition of InStyle Magazine a blurb about dresses over pants. Now I will admit, I’ve seen this style a couple of times on other bloggers and it’s not my favorite. But then again, I keep telling myself, this isn’t much different than a tunic over leggings, right? AND, then I also saw a blurb about it in People’s Red Carpet Style Magazine. So I went with the old adage that if you can’t beat them, join them!

And check below at the bottom of the post, because Carmen sent me her photo wearing the same thing!! See—we’re all crazy!

I knew this concept would get some push back from my models!! (That’s why I used this quote today-for a little irony). This is just not how we were raised to wear a dress so it’s hard to change our thinking! But here goes anyways! We also wore these same t-shirt dresses with a sweater over top and a shirt underneath.

So you have to tell me….are you open to this style of a dress over pants? Or is it too out there for you?

Jodie’s (50’s) Outfit:  I wanted to show different colored jeans under our dresses. I pulled out my white jeans since they are truly my go-to’s no matter what time of year. This pair is the coated variety, which is nice because they don’t collect kitty fur!

Styling our T-Shirt Dresses for the Colder Months.

Since I wasn’t going to wear a necklace, I decided to opt for some big, fun earrings instead. I actually found these at a thrift store many years ago, and I really like them because they aren’t too heavy on my earlobes!

Styling our T-Shirt Dresses for the Colder Months.

Now I wasn’t planning on wearing a belt with this look, but the cardigan (which is actually a sweater dress that buttons up the front) didn’t want to stay closed very well, so I grabbed the belt on the way out the door. I liked the colors of the belt with this outfit, but the beading competes a little too much for my liking.

However, at the end of the day I had an AHA moment, and turned the belt around backwards! Then the beading gave the rear view some interest, and the brown elastic (the back portion of the belt) tied in nicely with the brown of the cardigan! Of course, I didn’t get a photo of this change in my outfit—but hopefully you get the idea!

Styling our T-Shirt Dresses for the Colder Months.

Of course, I had to add in some brooches on the cardigan for the required bling!! These accessories were put on the sweater before I had grabbed the belt, so I thought they added a nice touch to the solid colored brown. I’m showing the outfit below without the belt, which is what I saw in the mirror at the beginning of the day.

Styling our T-Shirt Dresses for the Colder Months.

Dress: Mom made it (similar here in green & white)~~Jeans: LOFT (similar here)~~Cardigan: Max Studio (similar here)~~Shoes: Jessica Simpson (similar here)~~Belt: (similar here in a maya design)~~Earrings: (similar here)~~Brooches: (similar here or here’s a dragonfly by itself)

Nancy’s (60’s) Outfit: I knew Nancy had these sage green skinny jeans in her closet, so I thought they’d tie in well with the colors of the dress.

Styling our T-Shirt Dresses for the Colder Months.

Nancy’s dress is more of what I’d consider a color blocked dress with the green on top and stripes on the bottom. We didn’t add a belt to the outfit in the last post, so I thought I would for this one.

Styling our T-Shirt Dresses for the Colder Months.

The shoes are Nancy’s metallic ballet flats that she bought for touring around on her last river cruise. The belt and earrings are different metallic colors, but then the necklace ties them all together!

Styling our T-Shirt Dresses for the Colder Months.

This necklace has sparkles on the reverse side (and I’m sure that’s the “right” side), but it looks just as good and a little less “dressy” when it’s turned around. Have you ever reversed your jewelry like this?

Styling our T-Shirt Dresses for the Colder Months.

Dress: Mom made it (similar here with some color blocking)~~Jeans: Chaps (similar here in an ankle version)~~Shoes: Ecco (here in other colors)~~Belt: H&M (similar here)~~Necklace: (similar here a smaller version)~~Earrings: (similar here)

Charlotte’s (70’s) Outfit: For my mom’s outfit, I had her wear her moto jeans that we bought at a consignment shop. These jeans are a tidge long to wear with flats, so we always pair them with heels.

Styling our T-Shirt Dresses for the Colder Months.

Mom’s dress has a “v” cut out in the front like mine does, so she wanted to close it with her matching pin for this look!

Styling our T-Shirt Dresses for the Colder Months.

Both the earrings and bracelet are the same colors that are in the dress. However, since they are the darker versions of the purple, I think they blend in well!

Styling our T-Shirt Dresses for the Colder Months.

Mom just came up with the idea about shortening these jeans while we were taking the photos. She thinks she can shorten them at the knee area where there is a seam, since it can’t be done at the bottom because of the zippers. So stayed tuned to see these jeans with flats sometime in the future!!

Styling our T-Shirt Dresses for the Colder Months.

Dress :Mom made it (similar here in B&W)~~Jeans: DG 2 (similar here)~~Shoes: SRO (similar here in a suede or here with a lower heel)~~Pin: (similar here in lighter colors)~~Earrings: (similar here)~~Bracelet: (similar here)

Carmen of Fashionable Over 50: Carmen and her daughter are showing the same dress—and they are both wearing it over jeans! It’s nice to know that I’m not the only crazy one!!

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I rounded up some other jeans for $100 or less, since they are such a staple nowadays!

  • The concept is good but IMHO, I think that the proportions with your dresses was off. I think that a dress over pants looks would have been better is the dresses were shorter (more tunic length) or longer (midi length). I’m delighted to have you among my regular Fine-Whatever link up contributors.


    • Jodie Filogomo

      Ahhh…now that’s an interesting thought Rena!! I always know that proportions are important, but I don’t think about them much!
      I’ll have to try this again with different dresses (if mom & Nancy will let me—I got the eye roll more than once–ha ha)

  • I love that you ladies try new things and confront intimidating trends instead of shying away from them. I’m not a big fan of this look either, but fashion is about experimentation. You’re not going to get it “right” every time, nor do I think that’s the purpose. I don’t often wear the dress and leggings look, so of course a bulkier pant would be even less appealing to me. Still, good for you three for giving it a go. You never know unless you try!

    <3 Liz

    • Jodie Filogomo

      I think you’re right, that the purpose isn’t to be perfect! How boring would that be? I almost feel that when people talk about “their style”—it almost makes it too predictable!! And as much as I like planning, I do like a little bit of surprise and interest!!
      Besides, when I have these fails, it almost makes me want to figure out how to make them better. As opposed to the posts that look fine—there’s no challenge there! Silly, huh?

  • Well, as you know, I am now a huge fan of purple an mint so I am swooning over all 3 dresses! They are so bright and cheerful! Also, as you know, I am a huge fan of dresses over jeans and I wear that combination quite often! All three looks are fun. But I could see how Nancy and Charlotte would have resisted such styling. It really is outside of the comfort zone for most. But great things happen outside of our comfort zones…as is evidenced by this post! I think if you view your dress as an oversized tunic maybe it is easier to pair it with pants! Thanks so much for linking up with me On the Edge!


    • Jodie Filogomo

      Thanks for giving us the thumbs up on this Shelbee!!
      I have to admit that it’s hard when many tell you they don’t like it! But it’s way more fun to try new things and get creative with our clothes, right?

  • Not my fav look either, Jodie, but it might work better on me with solids instead of any sort of print. Simpler, which is my preference these days. As to changing up jewelry – ALL the time! I have worn necklaces “wrong side out” as well as adding chains to the back to make them longer – and have even added pins to chains to make a brand new necklace look.

    But you never know until you put things on your very own body – at least I never really do.
    (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

      I really think that’s the right attitude Madelyn! We might as well try out the new styles & trends–they are only clothes and it’s not like it’s going to hurt!!

  • Terri Webster Schrandt

    Not a fan, I’ll stick with leggings…you look great, however. It would feel too bunchy with the dress and jeans competing for tummy space 🙂

    • Jodie Filogomo

      I totally get it, Terri!!
      It’s still not my favorite look, but I’m glad I tried it.

  • Tina von tinaspinkfriday

    Shirt Dress and Jeans, hm… it looks good. I think I never have worn pants and Shirtdress. Maybe I should try….
    Xo Tina

    • Jodie Filogomo

      It is an interesting concept, Tina!! I’m still not 100% in love with it yet, but I bet the more I see it, the more I’ll love it!!
      Thanks for considering it!!

  • rae

    cooool! 🙂

    xoxo, rae

    • Jodie Filogomo

      Thanks Rae!!

  • Well, I do like pairing tunics and jeans. And I haven’t tried a dress yet….but if I was still living in Wisconsin, I would be all over that! It sounds like a great way to stay warm and still wear your dresses. You ladies all look great with how you styled it too. I think it could be a tricky one to style sometimes. But you all did awesome!

    • Jodie Filogomo

      Thanks Lindsey!
      I’ve had a couple of suggestions of how to make it better…maybe I’ll try it again next year and see if I get a better response!??

  • Versatilestylebytracey

    Doing a dress with leggings has been done and now wearing them with jeans is the next evolution, lol

    • Jodie Filogomo

      What a great way to describe it—evolution! Then again maybe women my age and older aren’t ready for this??

  • Amy D. Christensen

    Hey just because it seems crazy doesn’t mean we should just throw it out the window! I think this trend works, but I also think you have to have the right combo of pants and dress. You have more of a skinny jean style, which I think works well. I think I would have liked Nancy’s better with her pants rolled or cuffed and then with your mom’s I think it would be cool to have a denim jacket or vest added to the top….just some thoughts. I love that you gave it a try. Well done! – Amy

    • Jodie Filogomo

      Those are great ideas, Amy!!
      I doubt that mom & Nancy will try this again, unless I style it for the blog again. But it might not be a bad idea to revisit it. I could do a series of the misses—and how to correct them!!

  • Laura

    I am not sure about this trend honestly. But I haven’t tried it so I can’t knock it! I tend to prefer it on dresses that are shorter anyway which makes them more like a tunic.

    • Jodie Filogomo

      I totally get it Laura! It just seems wrong somehow.
      But I do remember thinking the same thing about skinny jeans too—so at least I can say I tried it.
      I have to admit, I almost like the outfits that don’t turn out as well—because they are more interesting and make me want to restyle them! Crazy, right?

  • You know, I used to not like this trend but I’m coming around to the idea of it. It actually looks really cute! And the colors in all of your outfits scream Spring! Happy Friday!


    • Jodie Filogomo

      Thanks Liz!!
      Right? If you just get past the idea that there are jeans under the dress–maybe it’s not the worst thing ever?!!

  • I’m all about repurposing your wardrobe! I love how you ladies did that with the dress!


    Tamara –
    Sephora Haul & Giveaway

    • Jodie Filogomo

      Thanks Tamara!
      It’s definitely a different look!!

  • Mother Daughter

    I also have seen this look around lately, on people and in magazines, not something I am fond of though. lol Good for you for the effort though. And I love your quote, I seem to have a problem not doing it. lol

    • Jodie Filogomo

      That’s why the quote spoke to me Victoria—because that’s me at times too!!!
      Thanks for your voice!

  • I always liked it! I am wearing it today top as you know and I van remember that I wore it when I worked in a store, twenty years ago. Everybody said: oh you cant wear a dress over trousers! Well, ladys, now its on many blogs! And I still love it! Well done lady s!

    • Jodie Filogomo

      Well this just goes to show that you’re way ahead of the crowd, Nancy!!
      Good for you!!

  • OH WOW!!! Great fashionistas think alike!! 🙂 Check your inbox!


    • Jodie Filogomo

      So I had to add it to the post—-we could say “twinsies!!!”

      • So fun Jodie! Honestly, not only are we twinsies, but this is the plan for my next post: T-shirt dress for all seasons. I want to include you gals in my post!

        Thanks for including me and my daughter! ❤️

        • Jodie Filogomo

          Oh, I’d love that Carmen!!
          How funny that we were on the same wavelength.
          Feel free to just grab one of the photos from my blog–i’ll be gone all weekend on a mini vacation!!

  • I’m still trying to get used to the idea of dresses and pants. So funny that we both discussed this today on our blogs. Thanks for sharing these looks!

    • Jodie Filogomo

      We were definitely channeling each other Kathrine! But I do think your outfit really hit the mark better with the slits up the side of your sweater!!

  • Judy Gramith

    I love the long sweater and the belt together but NOT with the colors or stripe of this particular dress.
    I also have to give a thumbs down on the combinations that Nancy and Charlotte are wearing. I think the pants just look really awkward. If the dresses were neutral, (or complimented the color (s) of the pants) a bit shorter, and much wider at the bottom the look would be more balanced.
    I’m not averse to the combination of dress and pants but I think it requires specific, balanced, complimentary pieces. Purple or green skinny jeans would suit my taste better.

    • Jodie Filogomo

      Well you know what that means, then Jude? We need to go shopping—ha ha!! I bet my mom would love purple jeans!!

      • Judy Gramith

        Oh not necessarily! If you all like these outfits then you should stick with them.
        I am a BIG fan of these dresses that Charlotte made. I love that she creatively did each one a bit differently. I think they’re great enough to stand on their own.

        • Jodie Filogomo

          Well…I wouldn’t say Nancy & mom liked these outfits–haha!
          Mom didn’t put up as much of a fuss as I thought she would. But Nancy gave me the thumbs down! But aren’t they such good sports for wearing it anyways??
          I was approached in the Target parking lot by a women who said she loved my outfit when I had this on! Of course, she was an artist!! You know those artists?…they have an interesting take on life!!!

  • I have seen this in the magazines too and admit to not loving it myself. I do love that you all tried it though! And I actually think it looks good on you. I always appreciate how you all make me think.

    Amy Ann
    Straight A Style

    • Jodie Filogomo

      Thanks for such a nice thought Amy!
      I realize that we don’t want to look silly by what we wear, but I think I’m finally learning that we can try new things and have fun with our clothing and style!! But heck–it’s only taken me 50 years–ha ha!!

  • Hey Jodie! I’ve seen this look on other blogs too and I think it really depends on the dress and the pants. Like, I really think you look is great and I think it’s b/c you are wearing slimmer legged pants. Nancy’s pants width I’m not crazy about where I think your mom’s flare jeans could work if the dress was more flared too. I’ve seen the look with a really slouchy, asymmetrical top and bottom that seemed to work. Good for you ladies for giving it a try and showing us the results!
    Have a great weekend!


    • Jodie Filogomo

      What a great observation Julia!!
      I was trying to make sure we all had on a slightly skinny jean version, but maybe if the dress is flared, then flared jeans would work!! How interesting!!
      I’m sure my mom & Nancy will never be wearing this look again–ha ha! But how do we know if we don’t try, right?

  • I really like the tip to reverse the jewelry!! There are a few necklacesof mine that would fit that!!

    • Jodie Filogomo

      Thanks Elle!! It’s interesting how some of our jewelry can be almost a two in one this way!!

  • There are plenty of styles that–when I first saw them–were a “no” for me. But the persistence of you fashionistas brought them mainstream, and lo and behold…guess who’s wearing hi/low shirts, ankle boots, gladiator sandals, and lower rise skinny jeans? Me… and everyone else.

    SO…this might not be a look I’d try today, but who knows? You, Jodie, are someone who teaches me to never say “never”.

    • Jodie Filogomo

      And I’m still learning this never say never too, Em!! In fact, yesterday we were taking photos for the blog and I had on a dress. But later that day we went to the grocery store (which is always freezing cold) so I slipped on a pair of jeans with the dress instead of changing out everything. And I would have never thought to do that before blogging! And I don’t think that everyone stopped and stared at my outfit–ha ha!!
      And I was exactly the same way with skinny jeans (among the other items you listed)—aren’t we birds of a feather??

  • The dress one pants trend won me over after seeing it on the red carpet. As someone who prefers to cover up, I do this a lot. thanks for sharing this lovely post, rock on! Have a great weekend.



    • Jodie Filogomo

      It’s true—seeing it in mainstream, does make us appreciate it more, Yasmin!!
      Thanks so much for reminding us of that!!

  • Karen

    It’s too ‘out there’ for me, but after looking through these pictures several times it started to grow on me. I think that it works because things that seem ‘out there’ always work for someone somewhere, and these days I don’t think anyone is surprised when women mix up their clothes like this. They just think you are being original. And you are. Today my take-away is that I can turn necklaces over for a different look, and why not wear a belt backwards, deliberately!? I do love that quote Jodie!

    • Jodie Filogomo

      I’m right there with you Karen! I’m still not convinced that it’s a good look!
      But I have to tell you that I did go places in my outfit. And there was a lady in the Target parking lot that stopped us to comment that she loved my outfit. Now, granted she was an artist—-so maybe that’s the thing. Artists are more creative, right? So maybe this is one of those “artsy” outfits??
      And you’re right about getting ideas from trying things out!! Turning the belt around was quite the light bulb moment—so hopefully I’ll remember it for other times!!
      Thanks so much for your voice in this!! I love hearing all the different opinions and perspectives!!

  • Bernadette Laganella

    Interesting idea but too much fabric for me.

    • Jodie Filogomo

      I totally understand Bernadette!!
      I’m still not sold on the look (and I’m sure my mom & Nancy won’t be wearing it on their own very soon either)! But I thought I’d give it a go!