Style and Styling

4 Ways to Style a Shirtdress: Fall Edition

Happy day, reader dear!

Well, I’ve gone and done it. I’ve broken one of my own rules. I’ve always had in my mind that I wasn’t going to style items that weren’t in my own wardrobe. And I certainly wouldn’t buy something just to style and return it to the store afterwards. Well, today I am styling a piece that isn’t in my wardrobe because I couldn’t do a fall shirt dress styling post with my oh so summery shirt dress. There. Confession made.

It all started when I did a Facebook Live video about wearable Fall/Winter 2019 trends at my favorite consignment shop. And: I found a gorgeous purple linen shirt dress. Which: Reminded me of my 5 Ways to Style a Shirt Dress (for summer) post. And: The promise at the end to do a fall version. But: I didn’t have a fall vibe shirt dress in my Fall 2019 capsule. I don’t have a fall or winter shirt dress at all! So: Tara of Encore Consignments flew to the rescue. She was so kind as to loan me that gorgeous purple linen shirt dress for a styling session. With pieces that ARE already in my wardrobe. So: Without further ado, and with less breast beating… 4 Ways to Style a Shirt dress: Fall Edition.

I love this shirt dress for our falls! Its rich color plays so nicely with fall’s olives, browns, taupes, russets, and berries. It’s linen, cool enough for our hot days. The gorgeous purple makes it feel less summer than fall. And it’s beautifully lined! I wish it were my size. I’d buy it in a heartbeat. Sigh. That’s one problem with shopping consignment… You never know what you will find in your size and what will turn out to be unrequited love.

I had in mind “office” for this first outfit. I belted the dress, and buttoned the sleeves after cuffing for a French Cuff look. I’d have preferred a smooth leather belt here, but I don’t have a brown one, so braided it was. The colors of the leopard pumps and tortoise shell bracelets are repeated in the buttons and the scarf. I love these faux tortoise bracelets because they don’t make noise the way metal bangles do! Perfect for work.The criss-cross knot in the scarf gives this look a touch of equestrienne chic, and would also look fabulous tucked into the neckline. Style Tip: If you choose to tuck and the scarf tails are long enough, tuck them under your bra band in the front to keep the scarf from slipping and sliding.

Here’s another office look, albeit a bit more relaxed. I wanted to try another dress over trousers outfit. They are comfortable, practical, and a little sassy. This time I went for lots of color, but because they are all deep, they don’t shout. Layer the shirt dress over narrow teal trousers, belt with the scarf from above as a sash, and pop on suede loafers. Heels would look amazing here as well! Style Tip: Repeat accent colors in threes for an intentional but not “matchy” vibe. (I repeated the loafer color repeated in the sash, bracelet, and lipstick!)

Now let’s move onto some more playful looks! I know many of you live in much cooler climes than we do here, so how about a look for chillier days? Why not play a safari theme by belting the barn jacket and pulling on boots?

This last outfit made me regret the utter lack of khaki (or for me, taupe) in my wardrobe! I would love to see this shirt dress as a duster over khaki pants and a tank or tee. Or oatmeal. All I have is white, and it didn’t have any fall cozy! This combo feels perfect for a day of sightseeing. A drive through the fall colors, some small town browsing, and a nice little lunch outside in the fall sunshine. Sounds lovely, no?

If this post catches you on a weekday, and a day of sightseeing leisure isn’t on your schedule, slip the leopard pumps on with the brown column of color, and head to the office! If you teach, keep on the comfy shoes (I highly recommend L’amour des Pieds. #notanad #imho) and swap the little crossbody for a teacher sized tote.

My apologies if this post reads as a hastily assembled punctuation party. I had technical issues for a day and a half this week that left me scrambling to pull this together. Back to Shirtdresses. Or Shirt Dresses (You will see both, so search for both when on-line shopping.) How about you? Do you wear have a shirtdress you can take into fall? Denim would be amazing! Or do you retreat into only trousers and jeans when summer takes its leave? Please let me know in the comments below. I love to hear from you…

Stylishly yours,


  • Leslie Susan Clingan

    I have two shirt dresses that I really like to wear. They might be the best silhouette for me. Had a darling burnt orange corduroy one but I singed it when ironing. I have worn mine with shawls and kimonos. Going to try my chambray with my olive utility jacket, thanks to your inspiration.

    • closetplayadmin

      Hi, Leslie! The chambray with olive sounds darling! I almost wept when I read about the singe… That’s so sad! I love the idea of shirt dresses, but I don’t like shirt collars on me, so finding the right one is a bit of a struggle. I’d love a denim/chambray. Enjoy your weekend!

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.