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.)


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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!


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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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