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3 Ways to Wear a Classic Shirtdress

2025 Style Series
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June 17, 2025

During the warmer months I love opting for the ease of a dress. With a few well chosen accessories, it’s a one and done outfit. And no dress is more versatile than a shirtdress. While there are in fact so many more styling options to choose from, today I’m sharing 3 of my favorite ways to wear a classic shirtdress for summer.

3 Ways to Wear a Classic Shirtdress this Summer

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A shirtdress is simply one that features several details usually found on a men’s dress shirt, such as a front button placket, a traditional shirt collar and sleeves. But as this now classic dress has evolved over the years, it has become more varied in design. You’ll find sleeveless, short sleeved and long sleeved shirtdresses, as well as those with a cinched waist and other distinctly feminine details. Shirtdresses are traditionally made in fabrics also indicative of a men’s dress shirt, such as cotton or linen. But you’ll also find them in knits and even silk for dressier effects.

I always feel good about adding a shirtdress to my closet because I know it’s a silhouette that flatters my frame, gives me a little versatility in styling and will never go out of style. The classic shirtdress is also a good choice if you want to look a little more polished and buttoned up, pardon the pun. Elements such as the collar and an optional belt elevate this dress for work, church and even more formal occasions. But you can also easily dress it down with the appropriate styling choices. Let’s see the 3 ways I’ve worn the classic shirtdress for summer.

Wear a Classic Shirtdress Loose and Flowy this Summer

For a summery look that is truly easy breezy I enjoy wearing a straight, full shirtdress buttoned, but uncinched at the waist. This organic cotton poplin shirtdress in pale sky blue is super soft and cool on the skin. It’s also available in white and ink (dark navy) options. I’m wearing a size small, as I usually size down in this brand. It also comes in petite and plus sizes.

Wear a Classic Shirtdress Loose and Flowy

Sunday I wore this poplin shirtdress with soft taupe block heeled slides and accessorized with a green and blue kerchief and a green handbag. While I realize that this way of styling a classic shirtdress is not figure flattering, I still think it is beautiful and flowy. Remember, sometimes we have different style goals. And on a hot, humid summer day I like to look as fresh and cool as I feel in an uncinched shirtdress.

Wear a Classic Shirtdress Loose and Flowy
cotton bandana // necklace and earrings (c/o – use code KAY20 for 20% off) // diamond pave huggie earrings (sold separately)

To keep the look summery fresh, I wore a cotton bandana simply knotted at my neck. No need for a fussy tie or a voluminous scarf.

Wear a Classic Shirtdress Loose and Flowy
cotton poplin shirtdress // similar sandals // handbag // cotton bandana // necklace, bracelet and earrings (c/o – use code KAY20 for 20% off) // diamond pave huggie earrings (sold separately) // watch

For a loose and flowy aesthetic enjoy wearing your favorite straight shirtdress unbelted. It’s forgiving, of course, but also so summery fresh.

Wear a Classic Shirtdress Belted this Summer

But I can absolutely wear that same cotton poplin shirtdress belted. Even a straight shirtdress that doesn’t feature a designated waistband can be cinched for a figure-contouring effect. The fullness in the dress allows it to gather softly around your form with a simple belt from your closet.

Wear a Classic Shirtdress Belted for Summer

For a slightly more casual look I wore cognac accessories this time, cinching the dress with a thin caramel leather belt. I love the combination of leather, straw and soft blue for summer.

Sandals with a Classic Shirtdress
sandals or here // similar bag (mine is no longer available)

The T-strap sandals and top handle lady bag accentuate the traditional vibes of the belted shirtdress.

Simple Jewelry with a Classic Shirtdress
necklace, bracelet and earrings (c/o – use code KAY20 for 20% off) // diamond pave huggie earrings (sold separately) // sunglasses (c/o)

This time I wore my fine jewelry from Penelope Jewelry. You can use code KAY20 to get 20% off your order at Penelope.

Wear a Classic Shirtdress Belted for Summer
cotton poplin shirtdress // necklace, bracelet and earrings (c/o – use code KAY20 for 20% off) // diamond pave huggie earrings (sold separately) // sunglasses (c/o) // similar belt (mine is no longer available) // sandals or here // similar bag (mine is no longer available)

I know that adding a belt to a shirtdress can be a little scary if you don’t have the slender figure that you once had. Trust me, my waist is not tiny. Before you rule it out, try it. A belt adds definition and creates a very pulled together look, so it’s worth a try. And if it just doesn’t work for you, never mind. There are other options.

Wear a Classic Shirtdress Cinched with a Sash this Summer

For my third ways to wear a classic shirtdress this summer I’ve switched into a beautiful new dress that I was gifted by Ann Mashburn. Her website is full of classic menswear inspired feminine pieces that could serve as staples in a curated closet. Honestly, this short-sleeve classic shirtwaist maxi dress is one of my favorite pieces I have ever been gifted by a brand.

Wear a Classic Shirtdress Cinched with a Sash

The green/blue block print is both timeless and modern, and the 100% cotton fabric is lightweight, silky soft and floaty. The details are pretty amazing, including a well placed hook-and-eye closure at waist, substantial Trocas shell buttons, on-seam side pockets, a softly pleated skirt and a beautifully stitched deep hem. I am beyond impressed with this new-to-me brand, which originated in Atlanta.

Wear a Classic Shirtdress Cinched with a Sash
Tory Burch watch // necklace (on sale!) // similar bracelet // earrings

This time I styled this cinched waist shirtdress with its generous self-belt. By the way, the dress fits true to size; I’m wearing a medium for a perfect fit. I wore my Julie Vos jewelry with this look and added my Tory Burch watch.

Pretty Sandals with a Classic Shirtdress
leather sandals // handbag

For a dressy look I wore the shirtwaist dress with some on trend and oh-so-feminine strappy heeled sandals. These comfortable 2.3″ heel leather sandals also come in black and ivory, and they fit true to size. They’re perfect for a wedding guest outfit or other dressy ensemble, but work nicely for church and dinner dates, too.

Wear a Classic Shirtdress Cinched with a Sash
short sleeve shirtwaist maxi dress // leather sandals // handbag // Tory Burch watch // necklace (on sale!) // similar bracelet // earrings

Below I’m sharing SO MANY beautiful shirtdresses that are perfect for the summer. I’ve tried to collect dresses that will stand the test of time so you can wear them year after year, but I’ve also found options in a wide range of prices. Just click on the photo to get more details, including size options and different colors and patterns available, and to shop. Click the arrows on the sides of the shopping widget to scroll to the left and right for more options.

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Blessed for My Day

I still remember when I “found” the Bible. I’d actually already had one on my nightstand for years, and I’d even read parts of it frequently. But I “found” it when I was 26 years old, a new mom and a new pastor’s wife. I’d experienced my first real season of turmoil when, on the same day, my husband had a seizure and I gave birth to our firstborn. My world was rocked and I was desperately looking for stability, security and hope for my future.

Interestingly, I came across a different book in my parent’s bathroom when I was visiting one day. The book was Lord, I Want to Know You, by the recently departed Kay Arthur. After reading just a few pages I asked my mom if I could take it home, where I devoured it in just a few days. That book taught me that getting to know the God of the Bible through careful reading and study of the Bible could not only give me the security I longed for, but it would also satisfy every other soul hunger. Indeed, I’ve been feasting on the Word of God daily ever since. Have you found the book? When? Has it changed your life?

Moreover, Shaphan the scribe told the king saying, “Hilkiah the priest has given me a book.” And Shaphan read it in the presence of the king. When the king heard the words of the book of the law, he tore his clothes. ~ 2 Kings 22:10-11

xoxo, Kay
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17 thoughts on “3 Ways to Wear a Classic Shirtdress

  1. Thank you Kay
    What a pleasant reminder that I once had a navy cotton shirt dressed that I loved. This will be the inspiration I need to look for one appropriate for this stage of my life.

  2. Blessed for my Day– My love for reading the Word has grown immensely over the last 8 – 10 years. When I retired from teaching, I began reading through the Bible each year, using several different reading plans (one of my favorites is Charles Stanley’s Life Principles Daily Bible – thank you for calling this one to our attention!). With each reading, I see more and I learn more. What an incredible gift God has given us with His written Word! He truly loves us!

    1. I’m so glad you have enjoyed the Charles Stanley Life Principles Daily Bible, too. It’s a treasure and I never tire of it. Thanks for sharing.

  3. Both dresses on you, stunning. Love the first dress, belted and accessorized with cognac. Love the second with those DV dress sandals. In fact, I think you modeled the Mashburn dress better than the model on their website. BFMD: not coming from a Christian home, I was given my first Bible from a sweet friend in 1993. But stubborn as I am, I didn’t actually open and read it until 2006, and that is when the Lord changed my life.

    1. Oh that’s so interesting. And such an amazing testimony. God is good to be so patient with us, isn’t He? Thanks so much for sharing.

  4. Kay how old was your husband when he had a seizure? I just had one in April and then in May around Mother’s day I had a small Stroke. I hope he is well.

    1. It was over 30 years ago when James was in his 20s. He had another one about a year and a half later, so he went on medication. He’s not had one since then and the doctors never could find the reason for them. But he’s in very good health. I’m sorry to hear about your experience. I know that is very scary and concerning. Praying for good health ♥️

  5. Thank you so much for including some plus-sized options in your shopping widget today. I like the Nordstrom and Talbots options.

    1. You’re so welcome. I try to do that as often as possible. Sometimes you need to click through to see that they are offered in a variety of sizes. I’m glad you enjoyed the options.

  6. Thank you for a great blog. Looking for straw stretch belt to go with summer dresses to fit 37” waist and your recommendations sold out. Any other thoughts?

  7. What a great BFMD. My life was drastically changed 4 years ago from reading and studying the Bible. I left the religion I grew up in. Now I’m a Bible believing Christ follower. I look forward to studying Scripture. The blue shirt dresse looks so good on you because you’re tall. I would need less volume. I like how you styled it. My first junior size dress was a yellow shirt dress. I was 13 and my parents took me shopping that day. I still have a fond memory because it’s the only time both of my parents took me shopping for clothes. Most of the time it was only my mother. I think that’s why I’m partial to shirt dresses.

  8. I’ve done Kay Arthur’s Bible studies years ago as a young mom. They were deep but I learned a lot and it helped to do them with other ladies. I had not heard she passed.

  9. Hi Kay, oh yes we too have several days of really hot humid weather arriving beginning Monday of next week so like you I’ll be hunkering inside with our AC!
    I’ll try to walk my two miles around 6:30-7am. It’s really that sticky air that depletes my energy ! And then- my hair! Frizz!
    Linen and gauze to the rescue!

  10. I agree that a dress is a perfect option for summer. However, my mind is beginning to think about my fall & winter wardrobe needs. I also love to wear dresses in this next season but find them to be mostly offered in black or gray or weird color combinations. I get cold easily so only look for long sleeve options. Does anyone have dresses or brands to recommend that fit this criteria?

@dressed_4_my_day