If there’s one piece in my wardrobe that effortlessly marries comfort and polish, it’s the shirtdress. Whether I’m dashing out the door for a casual meeting, wandering the streets of Paris or looking for something that works in multiple seasons, the shirtdress consistently proves its versatility. I’ve started wearing them more and more in the past years and rely on them particularly for certain work days.

How to Style a Shirt Dress

Today, I’m sharing my favorite ways to style a shirtdress along with a few outfit formulas I return to again and again. If you’ve ever wondered how to make this closet staple feel fresh and chic keep reading for inspiration.

And don’t forget to learn how to tie a belt for belted shirt dresses! It makes all the difference in the look in my opinion.

Bonus: Many of the pieces I pair with my shirt dresses are tried-and-true favorites I’ve shared before on wit & whimsy that you can shop in My Closet.

Don’t miss at the end of the post where I’ve rounded up a lot of available shirt dresses in a variety of colors, prints and at various price points.

Why You Should Have a Shirt Dress in Your Wardrobe

There’s something timeless and classic about a shirtdress. I like that the good styles have structure without being stiff and they are feminine but never fussy. And most importantly, it’s an incredibly easy canvas to style; whether you lean more casual or refined.

A few reasons I love them:

• They work in every season.

• They flatter a variety of body types.

• They transition seamlessly from day to night when styled right.

• They pack well for travel (you know I love a low-effort, high-payoff piece when I am traveling!)

Whether cotton, poplin, linen or silk, the fabric choice makes a big difference in how the piece can be styled.

I find myself reaching for all varieties depending on the time of year and it is a piece I rely on for making me feel put together easily. 

That being said, shirt dresses when not styled right can read frumpy or matronly. Below is a guide on how to style a shirt dress and ideas of what to wear with a shirt dress to look elevated and stylish. 

What Should I Wear with a Shirt Dress?

With Kitten Mules

This is one of my favorite ways to style a shirt dress. My Manolo Blahnik Maysale Mules (recommend sizing up half a size) are the perfect ladylike addition to my favorite go-to shirt dress by Tuckernuck. 

I’m wearing the Tuckernuck Chloe Dress in a size L. If you prefer color, this dress comes in loads of fun colors. 

This one by Anthropologie has gone viral and looks really cute, too. It also comes in a lot of colors.

With Summer Accessories

I also have the Tuckernuck Mini Chloe Dress in Navy (size L) and it’s perfect for summer styling with a basket bag and woven ballet flats. 

While I usually prefer a midi dress this mini isn’t too short and great for summer styling.

Lightweight Fabrics

For summertime styling, I look for a linen shirt dress or a cotton poplin shirt dress. J.Crew’s Elena Dress is perfect (wearing a S). 

It also comes in a mini style if you prefer that.

Black and Navy

I also have the Tuckernuck Chloe Dress in Navy (size L) and I think it’s so cute styled with black summery accessories. Wearing a cute Madewell raffia tote from last summer and Emme Parsons sandals.

Never forget the power of adding a cute little scarf on your bag in a color or pattern that coordinates with your shirt dress.

Ladylike

In autumn and winter, I like a heavier fabric shirt dress. Me + Em makes some of my favorites shirt dresses for Fall and Winter like the one above from a few years back. I’ll pair it with a classic pair of pumps and a favorite bag from my bag collection.

Related: The Best Shoes to Own for Fall & Winter

You could also get creative with layering in the colder months. A shirtdress under a crewneck cashmere sweater gives the illusion of a skirt and top combo while keeping you warm and polished.

La Ligne makes my favorite knitwear for styling. You can shop my favorite styles in my La Ligne Sweaters Review.

Eyelet

Eyelet shirt dresses are so charming for Spring and Summer. This one is from Sezane a few years back but this one is similar in style. Love this classic eyelet one for summer, too. It looks perfect for a summer vacation or a bridal shower or baby shower. (There is a sleeveless version, too).

Related: Sézane Size Guide

Tonal Dressing

When in doubt marry accessories with the same color palette as your shirt dress or the accent color. The one above is old from AYR but this one I found is very similar. 

With Sneakers

I love the juxtaposition of a shirt dress with sneakers. To make it less sporty, I added a basket bag. A great way to make a shirt dress more casual and weekend ready.

With Stripes

With a solid colored shirt dress like this one from Frank and Eileen (wearing a M), I added a striped sweater draped over my shoulders. 

Frank and Eileen makes a cute ruffle collar shirt dress, too.

Accessorizing Your Shirt Dress

Accessories are what make each shirtdress outfit feel different—even when you’re rewearing the same piece. Here’s what I keep on rotation:

• Belts: A belt is your best friend for defining the waist and creating a flattering silhouette. I reach for tan, black or cognac versions depending on the season and what shoes or bag I am going to wear.

• Shoes: From espadrilles to boots, a change in footwear gives the whole outfit a new energy.

• Bags: I love pairing shirt dresses with crossbody bags when traveling, or with structured totes for days in the city.

• Hats: In summer, a wide-brim straw hat can complete the look (and protects your face so a win-win).

Final Thoughts: Make It Your Own

At the end of the day, what makes the shirtdress such a versatile piece is how many ways they can be styled to feel like you. Whether you’re keeping things casual or dressing up, it’s one of those pieces that always looks thoughtful—without ever trying too hard.

I’ve been wearing shirt dresses for over a decade now, and I love how they always seem to evolve with my style. From my early days in PR racing to the subway to now taking client and vendor meetings as a travel advisor or strolling through the Marais on a research trip, a good shirtdress has been a loyal companion for my lifestyle.

Shop Shirt Dresses

 

Let me know in the comments—how do you like to style your shirt dresses? Or do you have a go-to one you love? Because if so I may just want to try it!

You May Also Like:

• Linen Pieces I Am Loving.
• Some of My Wardrobe Favorites Under $200.
• Current J.Crew & Madewell Summer Favorites.