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.

Whether you’re styling a shirt dress with sneakers for a weekend outing, sandals for a European vacation or heels for dinner, it’s one of the most versatile pieces you can have in your closet.

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.

How to Wear a Shirt Dress Year-Round

One of the reasons I always keep a shirt dress in my wardrobe is because it works in nearly every season. In Summer, I style mine with simple flat sandals, a woven bag and minimal jewelry for an easy warm-weather look. Come Fall, I swap in ballet flats and add a lightweight trench or lady jacket.

During Winter, a long sleeve shirt dress pairs well with tall boots and a long wool coat. And then for Spring sub in ballet flats, sneakers or a block heel.

With a few simple accessory changes, a shirt dress can easily transition through the seasons and remain one of the most versatile pieces in your closet.

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 of shirt dresses, depending on the time of year, and it’s a piece I rely on to make me feel easily put together. 

That being said, shirt dresses can read frumpy or matronly when not styled correctly. 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 perfect for hot summer days.

Cotton Poplin Shirt Dress

For summertime styling, I look for a lightweight fabric — like a cotton poplin shirt dress. J.Crew has a great selection of shirt dresses like this smocked one, and this smocked cotton poplin shirt dress and this mini shirt dress.

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. Just add a little straw bag and strappy sandals to complete the look.

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

Related: 18 Sandal Styles Worth Buying

Ladylike Shirt Dress

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 Shirt Dress

Eyelet shirt dresses are so charming for Spring and Summer. This one is from Sézane a few years back but this one is similar in style. This sleeveless eyelet maxi looks perfect for a summer vacation or a bridal shower or baby shower, and this one is pretty as well. 

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 and this one are both similar.

With Sneakers

I love the juxtaposition of a shirt dress with sneakers. To make it less sporty, I’d add 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. 

Related: Best Sweaters for Spring and Summer

Linen Shirt Dress

A lightweight linen shirt dress is a true staple of my summer wardrobe, as seen above on Nantucket.

This $168 linen shirt dress can’t be beat, and is super packable. Just don’t forget wrinkle release spray!

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).

Make It Your Own

At the end of the day, what makes the shirt dress 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:

• Things I’ll Be Wearing This Summer.
• 18 Sandal Styles Worth Buying.
• South of France Summer Packing List.