2 Casual Fall Dresses

Hello, friends, and welcome back to 26 Days of Fall Fashion, a stylish collaboration between me and Cyndi Spivey! I’ve been on the hunt for some casual fall dresses to style for this series and maybe even to add to my closet. I know I show a ton of jeans, and that is truly what I wear almost every day, but there’s certainly something to be said for variety in one’s wardrobe, and several of you have asked me to style some skirts and dresses for fall.

I typically wear sheath style dresses because I learned long ago that it’s the style that looks best on me. It provides the structure my body type needs and flatters my curves. But sheath dresses tend to be dressy, and unless the material has a lot of stretch to it, it’s not the most comfortable style to wear around all day long running errands or working from home, so I decided to venture outside of my comfort zone and ordered some casual cotton knit swing dresses and shift dresses to try.

I got boxes in the mail from Gap, Old Navy, and J.Crew last week, and I had a little try-on sesh that I shared on my Instagram story. The feedback was interesting and quite helpful, and I’m sharing two of my finds here today.


These are both from Gap, by the way, so they’re reasonably priced. Plus, I got them on sale, making them even more budget-friendly! I only ever shop at Gap when they’re having a sale. It’s like LOFT, they run sales so often, there’s no point in ever paying full price.

SALE ALERT >> Get 30% off your Gap purchase with code ONEDAY, and get an additional 10% off with code BONUS when you order over $100. That promo ends tonight at 11:59 pm ET. 

That sale includes, of course, the Chunky Pointelle Sweater I styled yesterday! In fact, Gap has a lot of really cute sweaters right now. I love this, but I suggest sizing down. I also think this is really cute. You can see where my heart lies, right?? Ha! Anyway, back to dresses!

Dress #1: Slub T-Shirt Dress


I thought this dress was cute paired with my Converse Shoreline sneakers for a casual day at home or to run errands on a Saturday. I like the wide scoop neckline and the dropped sleeves, and the slub material is sooo comfortable. However, when I put this on for photos, my husband immediately asked if I was wearing pajamas, so the jury’s out on whether or not I should keep it.


It also has a seam detail down the back that I thought added a little something.


The bag I’m carrying is by Sole Society, and it’s a nice budget-friendly satchel if you’re in the market for one. It’s the perfect size — not to big, not too small. It also comes with a detachable shoulder strap.


I accessorized with a long pendant necklace, some Alex and Ani bangles, and a pair of crystal studs. My goal was to keep it simple and casual. (And yes, I’m aware the dress could have used an iron. I’m so bad about remembering to iron things! I need to invest in a little steamer, I guess.)


shop the look


Slub T-Shirt Dress // satchel // Chucks // sunnies // similar pendant

Dress #2: Softspun Knit Tank Dress


I tried this on first with the Converse, and then I switched to these booties for the photo shoot. Since the dress is sleeveless, I thought the booties would bring it into fall. It was hot the night we took these pictures, but I can see wearing a jean jacket over this when the weather cools down.


For this look, I changed bags, but I kept my jewelry the same… except evidently I lost an earring somewhere along the way. I didn’t even notice until I uploaded these pictures. I’m a mess!


shop the look


Softspun Knit Tank Dress // booties // Suki crossbody // similar pendant // nail polish

I still much prefer a sheath style on me, but I decided to keep the green tank dress for something different. I wore it on Saturday with sandals to my church’s women’s bible study, and I got several compliments.

When I wore the dress on Saturday, I wore a gold lariat necklace and this bracelet set. I thought the colors coordinated beautifully with the green of the dress, and together they have a great fall vibe. I only got an iPhone snap of that outfit, but this picture got over 400 “likes” on Instagram!


I think the striped dress is going back, though. Everyone seems to think it looks more like pajamas than a dress they’d wear around town. Some suggested that I belt it, but I am too short-waisted to belt dresses like this. It just doesn’t work for me. It’s something to consider, though, if you have more of a straight body type or a pear shape. The dress did get a lot of 5 star reviews on the Gap website, so evidently some people like it.

A friend stopped by when we were taking these photos on Friday night. She agreed with the pajama assessment on the striped dress, but she liked the green tank dress. My husband doesn’t care for either. He says they both add about 10 pounds, and I do see what he means. They’re not the most flattering looks for me, but I thought they were fun for a change.

I’m curious to hear your thoughts! I also found a really cute sheath dress from J.Crew that we photographed over the weekend. I can’t wait to share that one with you! I’ll keep looking for fun dresses to share, and I’m determined to style a skirt at some point. I’m working on that!

Be sure to visit Cyndi and see the fall outfit she’s styling today!

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46 Responses

  1. Good morning!

    I love casual dresses, so this post caught my attention right away…

    On the 10 pounds/flattering question: my take, fwiw, is the occasional difference that hair up/hair down makes. Happens with some of my own outfits, they become hair dependent. SO…my take is the dresses look cute in the top photos, but the green one works so much better (more flattering) with your hair down. Does that make sense at all?

      1. I agree! I love the green dress with the sandals but also think it will be so cute with booties and jean jacket and throw on a beaded tassel necklace for cooler weather, even with tights later. I have a similar dress in sapphire blue I wear year round like that. I love the green on you!!

      2. Yes it is so much better with the sandals. Not so “heavy”. I still just can’t get accustomed to booties with dresses. The picture with sandals makes all the difference in the dress. Isn’t it crazy how a couple of small changes can do that?

  2. Hi Jo-Lynne,
    I really like the green dress! Looks great! Would you mind sharing the size you got. I’m a similar build and it helps when I order online. I appreciate you trying out new styles! Thank you.

    1. Sure! I have the medium in both, but I think I might have preferred the striped dress in a small. That said, the model is wearing a small, so the medium is probably right for me, and it is supposed to be loose.

  3. I think that green dress is so flattering for running around!! Don’t think it adds weight–just think it’s fun! It hits at a good spot above the knee also. I’m one of those 400 insta likes haha

  4. The first dress looks a little big .I love the green dress on you with booties and sandals and you don’t look 10# heavier!????

  5. Sure…they are not a fitted type dress and maybe aren’t what we describe as truly flattering! But that’s where I think a vest or blazer can be so helpful! Sometimes it’s nice (IMO) to have a variety of pieces in your closet.
    They certainly add a little dressiness yet are casual enough for everyday. I do like the green one a little better—I”m not sure exactly why—maybe the color looks better on you?
    Whether you keep them or not, at least you tried them….you never know until you try, right?

  6. I agree with you about the flat sandals with the green dress. For some reason they just seem to work better. Although I suspect if you threw on a jean jacket over it, the booties would work great.

    I think the biggest issue with the striped dress is that it’s too big and loose. I am curvy similar to you and have found the key to pulling off this type of dress is getting it as fitted as possible without it actually being tight. Even if it is designed to be loose, it just looks better when it’s a little closer to the body.

    Do you think the green dress will work with taller boots in the winter? Would you wear tights or just have a couple of inches of exposed leg? I’m trying to figure out how to work a few dresses in for the winter. 🙂

  7. I like the green dress a lot! Not as much of a fan of the other. The large scoop neck I think is what is off for me personally. Your husbands comment cracks me up! I bought a dress that’s very loose this summer and it’s super comfy. My husband hates it. He said it looks like an old lady’s duster! Yet I’ve had so many compliments every time I’ve worn it from other women! ????

  8. I guess I’m in the minority here, I prefer the green dress with the booties. The combo makes the dress seem a more sophisticated than with the sandals. Both are cute looks though. It’s nice to switch it up now and then.

  9. I happen to think you are completely adorable in the green dress (especially the pic with your hair down). I’m not big on dresses, especially shorter ones, but I just love this. I can see a lot of versatility with this one.

  10. Jo-Lynne, The flat sandals look so nice with the green dress. While I do like the dress and the way you styled it, I agree with you that this style dress does not flatter you. While it’s good to have a little change up in our closet, shouldn’t we still love the item! Just a thought!

    Have a blessed day!

  11. I like the look of the green dress with the sandals too. With the booties I would definitely see it paired with a jacket. Agree with the other comments about the stripped dress.

  12. I fell in love with gap cotton dresses this summer and practically lived in them! So when I saw the tiny striped dress in navy with long sleeves (same as your cranberry colored dress) I loved it! But to avoid the “pajama look” I sized down to an extra small. I wore it to church with my olive military vest and leopard flats and looooved it! Living in Florida, I’ll be headed to gap to try the sleeveless one, I love it with booties! ????

  13. I like the green dress with the sandals the best. I think it will be cute in cooler weather with a jacket and leggings or tights and maybe boots? Thanks for all the ideas. I recently read that women with extra weight live longer than men who mention it! LOL. You certainly don’t have any extra weight but I do so if a dress like this makes it look like and extra 10 lbs then it’s certainly not the dress for me! I really enjoy your posts and ideas.

  14. I would size down with the green dress. I think it would be adorable with a denim jacket. I also think that it would look great with a blanket scarf – I’m seeing that on a lot of the blogs this fall. It would be adorable with knee high chestnut colored boots too! That green is a fantastic color on you!

    I’m not loving the striped dress.

  15. Definitely get a steamer! It’s so much easier than ironing. I don’t think I even own an iron any more lol. I think you may like the dresses more if you add a vest or jacket over them, that would add some definition at your waist without a belt.

  16. I recently bought a black dress in this style and had to go down to XS, which means it was made too large. Even at the smallest size, it fits very big. It’s very comfortable, and while it’s ‘cute’ I don’t think it really does much for me other than show off legs. Whenever I wear something very loose fitting, I love the comfort level, but I also feel as if people wonder what figure flaws I’m attempting to cover up. Most of the time, I’d rather just wear fitted clothing and remove the mystery.

  17. I think the striped dress looks so cute on you! I really like the green dress with the sandals in the bottom photo! Super cute!

  18. I also disagree with your husband on the green dress. I think it’s really cute. I especially like the sandals look you styled! I don’t think it adds weight and looks really comfortable and cute. It might be a little too light to wear with booties and a jacket, but looks great how you styled it for your bible study. Just my two cents.

  19. I love the color of the green dress, but I’d like a long sleeve to carry it more into fall and to wear with quilted or denim vests and scarves. The booties looked fabulous with it and you rocked the outfit. It makes a great summer to fall transition, especially for warmer climates.
    The other looks so comfy, but isn’t as flattering with the cut. It would make a great hang around the house or run to the grocery store dress.

  20. Hey, whilst I agree that sheath dresses are best on you, I still think these dresses here work, and they certainly make yo look on trend. I prefer the green one, I think the stripy one is cute but agree with some comments it seems a tad large. I prefer the green dress with sandals, but it could work with a laid back knee boot I think?
    Don’t agree they make you look 10 pounds heavier. This is just a different style that’s trendy now and I think most people need some time to get used to it. Hats off to you for showing us pics of outfits you’re unsure about! ????

  21. I think the sandals and your hair down with the green dress takes away 10 pounds plus the 10 your husband said it added 😉
    I agree wth others here that the booties just add bulk. Maybe your whiskey Frye boots and a denim jacket once temps cool down??

  22. I have a similar body-type and usually prefer sheath dresses too! I think the striped dress is just too big on you! You are just too slim for that much fabric! The green dress is adorable! It fits great! I have the booties in black, and when I wear them with dresses, I fold the top part of the bootie down like a cuff. It gives a longer leg line making the legs look slimmer. Let me know what you think of the bootie idea. Maybe I am doing this all wrong!

  23. I say this with love, I agree with your husband! They aren’t for you and you won’t get much wear out of them! More returns… HAHA! I guess I’m not much of a casual dress fan either. Prefer sheath style as well and for a dress up occasion.

  24. Oh Jo-Lynn, Since you invited comments on the dresses, I’d return both. You have a cute figure but these dresses are not complimentary of your figure or your style. In my opinion both dresses look cheap and that’s probably b/c you’re too classy of a gal to wear them! I always say, deep down we know what’s flattering on ourselves, My rule is, if I have to question whether a garment is too short, too tight, too sloppy or too low, it probably is and needs to go back on the rack.

  25. I really like the green tank dress when you switch the shoe that was a nice look for you and it looked comfortable. I can also see wearing a jean jacket with it for a fall look.

  26. I liked the green dress on you and liked it better with sandles. Maybe the booties would work if you also wore a jean jacket or cardigan? I would love a steamer also, but have no idea what to look for. Would you be willing to do a review or two on steamers?

  27. I like the green dress with your Tory Burch Miller sandals the best. You look darling.

    It’s a cute and comfy look for running errands or like you said you did, going to church bible study.

    Don’t like it with the booties….it’s too “light” and casual for those (if that makes sense).

  28. I bought a clothes steamer at Target and love It! It has made my clothes look better with very little time investment.

  29. I really like the green dress on you. It gives some shape even though it’s a swing style where as the striped one doesn’t and I love the look with the booties!

  30. I like the green dress–very cute on you. I didn’t think it added weight to you. I like it with both the sandals and the booties. Will be cute with the jean jacket when it gets a bit cooler. Fun!

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