I know so many of my readers share my affinity for a classic wardrobe. We appreciate that timeless pieces serve us well for many years, sometimes decades. But if we want to look relevant and current, it’s important to know how to style the classics in a modern way. This year we’ve been slowly making our way through a 2025 style series I’ve called Styling the Classics for the Modern Woman. Today let’s continue that series with a look at how to style the classic shirt dress for fall and winter.
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By the way, you can always find all of the posts in that 2025 Style Series through the link in the top menu. In fact, I also styled two classic shirtdresses for spring and summer in this post. I designated today’s blog post for “fall and winter” because I really think you could wear this outfit through the coldest months with perhaps the addition of tights, a warm coat and some gloves. Let’s see how I styled this classic piece for the cooler months.
Styling the Classic Shirt Dress for Fall & Winter
My olive green wide wale corduroy shirt dress is also available in a pretty cream that would be absolutely stunning on some skin colors and tones. But I think the olive option plays nicely with my green eyes. The dress fits true to size (I’m wearing a 10) and it comes in sizes XXS to XXXL, although some sizes are currently out of stock. It looks like they may restock, however, so you can leave your information on their website for an update. PLUS I’ve created a large collection of shirt dresses in a variety of lengths, fabrics and price points in the shopping widget at the bottom of the post. Now let’s talk about some styling keys for fall and winter.
Style Tip #1: Choose the shirt dress that is best for you.
I chose a midi length classic shirt dress for fall in green corduroy because I love this fabric for fall and winter. And I love a midi length on my 5’8″ frame. Also, this dress can be dressed up or down a little. But you may prefer a dressier shirt dress for work or church, like this stunning knit dress. Or you may love the corduroy but prefer a pretty plum shade or a modern print. I love this raw umber dress in a luxe knit. And this matte jersey shirt dress comes in a number of pleasing prints.
I will note that it seems to be harder to find mini length (or above the knee) shirt dresses. They seem to sell out fast. And I know that many of my more petite readers probably prefer them. Or if you have an apple shape and want to show off those stunning legs, you may want a shorter version, too. But while I love this red currant corduroy option and this off white modern option, they’re almost gone. However, I did locate a shorter option in seaport blue with slightly better availability.
Style Tip #2: Belt the dress if you possibly can for a flattering silhouette.
The beauty of a shirt dress is that you do not have to belt it. But if your body shape allows, belting will help define your waist, create pleasing proportions and provide a more elevated look. Most shirt dresses, including mine, come with a same-fabric belt or sash. But I chose to remove mine and wear a substantial brown leather belt instead. That said, wearing the same-fabric belt can be a nice option when you want to cinch in at the waist but you don’t want to draw attention to that area.
Style Tip #3: Add interest to the outfit with a scarf or substantial jewelry.
Most any time I wear a dress I find it best to add some interest near the face to draw the focus upward. You can do that with substantial earrings like these or a scarf. You can wear a larger scarf outside the collar like I’ve done or a smaller scarf or even a bandana tucked inside the collar. I’ve collected some to consider in the shopping widget below.
Style Tip #4: Complete your shirt dress outfit with knee high boots.
Of course you can opt for heels, flats or even sneakers when wearing a classic shirt dress for fall. I’ve done all of those. But during the cooler months my favorite way to go is with knee high boots. They help create such a stylish, elevated look. My chocolate brown Ally boots are some of the most comfortable I’ve ever owned. They fit true to size (use their size guide) and I wear them in the roomy calf version. You can use code KAYBOOTS for $50 off your first pair of Ally boots or booties.
Style Tip #6: Add a modern touch with a little suede.
Suede is a classic choice, but it’s so on trend this year. Wearing something suede or faux suede – whether it’s your belt, boots, bag, jacket or coat – will give a nod to this modern trend. Remember, when you’re wearing a classic, it’s best to add a modern touch so you’ll look in step with the times. My dark carob brown suede tote bag is roomy, but does have an internal pocket and a magnetic closure. It’s working beautifully with other brown accessories.
Do you have a classic shirt dress for fall? Do you prefer the longer midis or the shorter minis? If you’re looking for one to add to your wardrobe, check the shopping widget below. I’ve collected so many to choose from at a full range of prices. And I’ve stocked the shopping widget with scarves and my accessories, too.
Thanks so much for dropping in for a little style inspiration. Have a blessed and beautiful day!
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Blessed for My Day
What’s holding you back? Is there something you know you need to do…you even want to do…but fear is keeping you from moving forward? It certainly happens to me sometimes. Some people might assume that nervousness and anxiety is a sign that they should not proceed. But I’ve learned that God does not use fear to direct our paths. That’s the enemy talking to you instead.
God leads with a reminder that He loves us and wants good things for us. He also encourages us onward even when feel we lack the resources or strength because He has the power and the resources we will need. His strength is made all the greater in our weakness. And He exhorts us to be strong and courageous, pressing onward with one foot in front of the other because He is with us through the entire process. So don’t let fear hold you back, dear sister. Have victory in this matter today. Speak truth to yourself and go for it.
…for God gave us a spirit not of fear but of power and love and self-control. ~ 2 Timothy 1:7
Your BFMD was just what I needed to hear today!
Thank you ! I love the green shirt dress &
the scarf!
I’m so glad that spoke to you. Thanks for reading.
Your video with Erika was great! Thanks for sharing what goes on behind the scenes. Keep doing what you’re doing! You are great at it.
Thanks so much, Debbie.
I had the kind of day you mentioned yesterday. Those do happen and it’s ok. I’m short so these dresses are so long on me and do nothing for me. You look great in them and I’m always tempted to try them again but end up returning. Love how you added the scarf.
Yes, we all have to work with what we’ve got. LOL! But have you tried the shorter shirt dresses? They do seem to be hard to find, however.
Lovely, Kay. That dress is sold out in my size, but I’m no the lookout elsewhere. I can see wearing it with a quilted vest, wrap, etc.
I am 4’11” with longer legs and don’t hesitate to wear midi length. As always, you are very inspiring as are your followers.
Thanks so much for sharing, Carol. Yes, I actually thought about styling the dress with a vest for this post but went this direction in the end. I think that could be very fun!