8 Chic Versatile Ways to Style a Shirt Dress
If there’s one piece that truly earns its place in every stylish woman’s closet, it’s the timeless shirt dress. I ordered this one for last week’s dress post, and it impressed me so much with its versatility that I knew it deserved a post of its own. I’ve always gravitated toward pieces that can be styled multiple ways and work for a variety of occasions—and this shirt dress checks every box. Whether you’re planning a getaway or staying close to home, let’s explore 8 Chic Versatile Ways to Style a Shirt Dress.
What makes this dress interesting is it’s ability to be buttoned asymmetrically for interest allowing a more flattering silhouette if desired. The dress has two extra buttons on one side so you can button it straight up or asymmetrically. It is a crisp cotton poplin that would be great for travel, easy dinners or errands.
Keep it Casual with Sneakers
A pair of sneakers are comfy and provide an effortless look with this great shirt dress from Banana Republic.
I buttoned the dress asymmetrically for a defined waist and rolled my sleeves up, I am just more comfortable with a mid sleeve length. A pair of sneakers in a fun color for comfort, and a cross-body bag (a few years old new version linked) )adds dimension to the waist when properly positioned.
This dress is actually navy and white stripe but I am treating it as black and white since I rarely wear navy. I am styling it with my MZ Wallace crossbody (Quince has a knock off here) and Olukai sneakers in black. This look would be just as crisp with a pair white sneakers and a white jean jacket.
Layers-Style it with a Sweater or Jacket
What creates a better combo than a crisp stripe poplin shirt dress and a denim jacket? The jean jacket is vintage Ralph Lauren, on Poshmark here, and (customized by Mermaid Brooklyn). Sneakers are from Taos, prescription sunglasses form Caddis here.
Simple accessories, and an open-weave crew neck or cardigan sweater can add texture and provide warmth on a chilly evening. A blazer or leather jacket would work for other times of the year. Sweater can be found here, similar sandals here.
Add a Scarf or Wrap for a Pop of Color or Patten
An admitted scarfaholic, I can always come up with numerous outfit ideas involving scarves.
I am currently obsessed with these destin bandana scarves (pricey but worth it). My comfy sandals are from Eileen Fisher. (newer version here)
Accessorize for a Resort Look
Nothing captures the spirit of the season like straw or raffia.
Simple fit-flops (my current favorites ), bone bracelets and straw accessories from Janessa Leone, bag and her newest hat (with my added bandana) make this shirtdress vacation ready.
This straw crossbody from All Saints (last year’s model several on eBay here), vintage bone and bamboo bracelets, and my Helen Kaminski hat add textural interest. The sandals from Eric Javits (on super sale are comfy favorites).
Add Ethnic Accessories for an Unexpected Twist
I was coveting this beautiful bag from Laura Shepherd on Etsy and finally pulled the trigger (an anniversary present to myself ha ha). I am also wearing my vintage don lucas earrings and bracelet from my collection, and a flat sandal from Laidback London here. There are also a few pairs on eBay here.
I styled this dress with a straw belt and accessories but somehow failed to get a picture. I will pop it in tomorrow when I get a chance. It could also be styled as a duster with trousers or jeans, or boots (in cooler weather). You could also add a pair of heels (if you wear them), or toss it on as a swimsuit coverup for travel.
Shirt Dresses in Every Price Range
You might also enjoy this post from Real Simple, How to Style a Shirt Dress According to Stylists here, or my post How to Style One Denim Midi Dress Six Ways.
Thanks for reading 8 Chic Versatile Ways to Style a Shirt Dress. The shirt dress truly earns its status as a wardrobe staple—timeless, flattering, and endlessly versatile. With just a few thoughtful styling tweaks, this timeless piece can carry you from special occasions, to a casual weekend and everything in between. Whether you’re dressing it up with a statement piece or keeping it relaxed and effortless, the shirt dress is a true wardrobe warrior. I’d love to hear your favorite ways to style yours—drop a comment below and share your favorite look!
You look so great in this dress that I ordered one for me. I, however, looked frumpy in it and was oh-so-disappointed. It looked too wide on me if not buttoned asymmetrically and simply just “funny” when buttoned. I’m 5’3″ and perhaps just too short to make it work. Would you mind sharing your sizes in garments from time to time to help some of us make better choices? Do I remember correctly that you’re 5’4″? I always enjoy your posts and remember fondly my visits to Paso Robles when I used to live in California.
You always think of such creative styling ideas! I have that dress and will play with the asymmetrical buttoning. Brilliant my friend. xo
Because of your ideas, Cindy, I had an inspired moment recently . I have had an olive linen knee length shirt dress from LLBean hanging in my closet for a few years…yes, one of those purchases that linger…but my lower legs look like road maps…thanks Dad and my Scottish aunties ! 😅
I will put it on, maybe go out with it styled well, but invariably feeling uncomfortable.
So now …inspiration… it will be worn open…with a column of cream t-shirt and canvas pants, or perhaps instead black . Again with the same accessories…chunky boho necklace & earrings…but my legs are no longer an issue, and my confidence sores! A belt , which was another issue, is no longer required . It doesn’t matter what shoes or sandals I wear…likely brown leather or black loafers with leopard tops… because they no longer shorten the ‘colourful legs’ either. I have strong, useful legs, but just not attractive ones. This dress will now earn its place in my closet!
Hi Cath
You always thing things through and have so much to offer. I love that!!
Beautiful looks Cindy ! Have a lovely day 🙂
Hi Francesca
Thank you!! Hope you had a lovely Memorial Day weekend!
Such a fun post and fabulous dress! I’m going to sew a couple extra buttons off to the side like that on some shirt dresses I own and give that cool asymmetry a try. Thanks for the inspiration!
Hi Laura
That would be so easy to do!
I love that shirt dress on you!! Especially asymmetrically! Wish it came in petite, but it would be fun as a maxi too.
Hi Mary Ann
I wonder why it doesn’t come in petite?
Love the versatility of this simple dress. Currently in your town. Enjoying The Farmhouse one of the places you mentioned. Really a lovely remodel. Any shops here we should check out?
Hi Cristi
Here is the link to my list:
https://docs.google.com/document/d/1delvZlfQGjWHNPZsZfvrurhtmljyk4KjaS478ORRmEE/edit?usp=sharing
That dress is really clever the way you can style it asymmetrically. I would be tempted to get it but I already have a BR shirt dress in solid black from a year or two ago and this year, I bought a knee-length one from JCrew in a shade of olive green. I question if the color is going to be good for me but I want to have it as an alternate to my other neutral colors; not sure I want another dress of this style.
As always, you come up with fun, different ways to style this striped version and it looks very summery and comfortable.
Hi Wren
It sounds like you are set for shirt dresses!! We need to get together!!
But the sandals on that last ethnic look! That’s what we want to know!
Hi Penelope
They are from Laid Back London. I added the link and the link to a few on eBay. I have two or three pairs all of which I have purchased on eBAy or Poshmark!