shirt dress outfit ideas

18 Best Cute + Chic Shirt Dress Outfit Ideas for 2024

This post contains affiliate links to products, apps, and/or services. As an Amazon Associate, I earn from qualifying purchases. If you click through and purchase, I will receive a small commission on the sale at no additional cost to you. Clicking on a link does not result in a commission. I only recommend products or services that I personally use or believe will be helpful to my readers.

Check out what’s in this post

Updated 2/16/2024

I’m obsessed with shirt dresses. They’re one of those go-to pieces for your capsule wardrobe because they’re so versatile. You can get a lot of wear out of them. Like an oversized shirt, they’re infinitely sharp, structured, and put-together looking. You can dress them up or down and wear them casually, for work, or even for a special event. 

In this post, I’ll help you choose a shirt dress by body type, and I have 18 shirt dress outfit ideas for dressy occasions, work, and casual outings.

First, here are some things to look for in a shirt dress by body type. 

Styles of shirt dress by body type

A shirt dress is a classic piece that works for every body type. But here are some things to keep in mind to create the most flattering silhouette when choosing a shirt dress. Not sure what your body type is? Read my post, How to Look Good in Your Clothes by Dressing for Your Body Type.

A belted shirt dress that’s more fitted at the top and flares in the skirt acts similarly to a fit and flare style dress. They offer a roomier skirt on the bottom if you’re someone who is larger on the bottom than on the top, like I am as a triangle body shape with a size 12 bottom and 36-B top. For me, dresses that fit my lower half are usually too big up top. Choose one that is belted in the middle, and you can adjust the waist to work for your bottom half. 

For the inverted triangle who is larger up top than on the bottom, shirt dresses with a belted fuller skirt help to balance your proportions between your upper and lower body. Choose a style with a wide v-neck, a simple sleeve without a puff, and a top without breast pockets. A simple top minimizes attention received by your larger upper body. 

For the rectangle body type, your shoulders and hips are a similar width and you look great in just about anything. Choose styles that keep your proportions balanced and add some curves. Look for a puffy sleeve up top, a belted waist, and a fuller skirt. 

For the hourglass body type, choose a shirt dress that shows off your perfect proportions and narrow defined waist. Choose a straighter-cut shirt dress that hugs your curves with a belted waist. 

For the round or oval type, you’re curvy and may have a little extra in the middle. Look for a dress with a v-neck that’s belted at the waist and adds definition to your shoulders. Choose soft-flowing fabrics in solid colors, and keep it simple without extra embellishments, tiers, breast pockets, or visible hip pockets.  

What do you wear with a shirt dress?

There are so many different ways to wear your shirt dress. Dress one up with heels, espadrilles, or pointy-toe flats. Or wear them to work with a blazer or denim jacket and ballet flats or loafers. Dress them down with a pair of sneakers or flip-flops and a belt bag. 

How to dress up a shirt dress

Maxi dresses or midi length shirt dresses lean toward the dressier side simply because of the length. Adding some statement jewelry, a handbag, and elevated shoes dresses the look up even more. 

Ready to look at some shirt dress outfit ideas? Let’s dive in!

1. Black midi shirt dress with black pointy-toe flats and bag

This dress is from a lightweight fabric that makes it airy and easy to wear in warmer weather or transitional weather. You can absolutely create a chic outfit with a shirt dress. These suede black pointy-toe flats feel elevated and are my go-to shoes for a special occasion when I don’t want to wear heels but want a dressier look. They give this cotton midi shirtdress a dressed-up feel.

Black midi shirt dress with black pointy-toe flats and bag

Dress | Shoes | Bag

Wearing oversized statement pearl drop earrings and a fancy gold watch also gives off an elevated feel. This square Coach tote bag is a statement bag. 

2. Black midi shirt dress with nude strappy kitten heels and a nude shoulder bag

If you’re looking to elevate a simple dress, add bold jewelry. Notice how the chunky gold hoops and chain necklace grab your eye first. A gold watch and bracelet move the eye down to the arm and waist and say “elevated”. These simple nude strappy kitten heels dress up the look while being easy to wear. A nude shoulder bag ties into the nude heels.

Black midi shirt dress with nude strappy kitten heels and a nude shoulder bag

Dress | Similar Heels

3. Black midi shirt dress with espadrilles

Espadrilles are always a fresh and fun choice with a long skirt. Here I’m adding a nude shoulder bag that ties into the cream shoes. Oversized pearl drop earrings, a mother-of-pearl clover necklace, and a chain bracelet are so eye-catching. A straw hat with a black ribbon offers stylish sun protection. 

Black midi shirt dress with espadrilles

Dress | Shoes | Hat

4. Black midi shirt dress with a white blazer and strappy kitten heels

This look could just as easily be worn to work. A crisp white blazer looks super chic with a black dress. Then these nude strappy kitten heels add a bit of modern elegance to the look. Pearl drop earrings, a gold cuff bracelet, and my best black bag are the little details that bring it all together. 

Black midi shirt dress with a white blazer and strappy kitten heels

Dress | Similar Heels | Blazer | Bag

How to wear a shirt dress to work

5. Black midi dress with cap-toe flats

Here’s a great outfit for work. These Chanel-inspired cap-toe flats are one of my favorite ways to create a work-ready look. The cap draws the eye to the end of the foot, making the leg look longer. A gold watch, pearl drop earrings, and a pearl necklace create a classic look. 

Black midi dress with cap-toe flats

Dress | Shoes | Bag

6. Black midi dress with a denim jacket, Birkenstock thongs, and a tote crossbody bag

If you work in a more casual environment, here’s one of the best ways to wear your shirtdress if there’s a touch of a chill in the air. Pair it with a denim jacket, Birkenstocks, and a tote bag for an easy casual outfit that’s still workplace-appropriate thanks to the longer look of the dress. I loved wearing Birkenstocks when I worked with college students and had to walk across campus from my car to my office. Choose a thong style in black for a more elevated feel. A classic denim jacket is the perfect length to wear with a longer dress. Roll up the sleeves to draw the eyes to your waistline. 

Black midi dress with a denim jacket, Birkenstock thongs, and a tote crossbody bag

Dress | Birkenstocks | Denim Jacket | Bag

7. Black midi dress with blush ballet flats, a nude belt, and bag

You’ll notice that this black shirt dress is slightly more casual thanks to super soft material. This is the most comfortable dress ever to wear to work. Pair it with ballet flats and a similar-tone bag and belt and you have a cohesive and put-together look. 

Black midi dress with blush ballet flats, a nude belt, and bag

Dress | Belt | Ballet Flats

8. A striped short shirt dress with ballet flats

A light blue and white striped shirt dress is a quintessential summer look. This shorter dress has long sleeves and still works for the office thanks to its smart collar. Adding a light-colored belt, ballet flats, and bag pulls the look together. 

 A striped short shirt dress with ballet flats

Dress | Belt | Ballet Flats

9. Blue chambray shirt dress

This short blue chambray shirt dress is the best way to get dressed for work in a flash in the summer. One piece creates an instant outfit. Add ballet flats and your own belt for a more elevated feel.  Dress it up with some jewelry.

Blue chambray shirt dress

Dress | Flip-Flops

10. White shirt dress with nude accessories

A white shirt dress is crisp and summery. Since a white dress is simple, pair it with big gold accessories like earrings and a cuff bracelet to move the eye from the ears to the waist. Or choose a big gold statement ring. I swapped out the casual cloth belt for a more elevated nude belt that blends with the strappy heels and bag.

White shirt dress with nude accessories

Dress | Belt | Similar Heels

This is an Amazon Essentials dress and the pockets show through. Wearing nude bike shorts helps a bit. 

11. Black shirt dress with a brown belt, block heel slides, and a brown crossbody bag

Typically shirt dresses come with a cloth belt that creates a more casual look. For a more elevated feel, swap it out for one of your own belts. 

Here, I’m wearing a dark brown leather belt and crossbody bag. The color blends with these midnight-colored slides that have a similar tone brown block heel. I need to add another hole to the belt so that it cinches the waist tighter. 

Black shirt dress with a brown belt, block heel slides, and a brown crossbody bag

Dress | Slides | Bag (old) | Belt

How to wear a shirt dress casually

Let’s look at some casual looks that you can wear out to lunch or running around town on a Saturday. 

12. Black midi dress with a brown leather jacket and strappy ankle wrap sandals

This dress has a sweet look to it. So I love the juxtaposition of adding an edgy brown leather jacket and strappy flat sandals. Black and brown worn together add to the vibe for an interesting and intentional look that can take you from day to night.

When choosing a jacket to go with your midi length shirt dress, choose a waist-length jacket like a denim jacket or leather jacket, or a trench coat that’s the same length or longer than your dress.

Black midi dress with a brown leather jacket and strappy ankle wrap sandals

Dress | Jacket (old) | Sandals | Bag

13. Black midi dress with black platform flip-flops

Here’s that more casual shirt dress again. This time I’m wearing it with a black belt, black platform flip-flops, and a black belt bag. 

Black midi dress with black platform flip-flops

Dress | Flip-Flops | Bag | Belt

14. Black midi dress with brown slides, a brown bag, and a Breton stripe sweater

Pairing brown accessories with a black dress creates a contrast that’s very chic. If you want to create a complete color story, add a brown leather watch band in addition to brown shoes and a bag.

Black midi dress with brown slides, a brown bag, and a Breton stripe sweater

Dress | Slides | Bag | Similar Sweater

Throw a sweater across your shoulders for air-conditioned rooms.

15. Black midi dress with a denim jacket and flip-flops 

Here’s a more casual look thanks to a lighter denim relaxed fit jacket and leather flip-flops. Braided belts are back in style and I chose this one because of its deep brown tone. The braid adds texture for visual interest. 

Black midi dress with a denim jacket and flip-flops 

Dress | Similar Flip-Flops | Belt | Similar Bag | Denim Jacket

16. Black midi dress with Adidas tennis shoes and a belt bag

Wear sneakers with your midi dress for a casual look. This black Lululemon bag keeps your hands free and holds your phone and wallet right in front of you while you’re out running around. The Adidas sneakers add a fun twist to this look and an edgy vibe. 

Black midi dress with Adidas tennis shoes and a belt bag

Dress | Bag | Adidas

17. Black midi dress with white sneakers and a leather belt bag

White sneakers and a dress are perfect for a day of running errands. White sneakers have become a classic and combining a midi dress with them creates an interesting juxtaposition pairing a dressier piece with an athletic piece. Plus, your feet stay comfortable all day long. 

Black midi dress with white sneakers and a leather belt bag

Dress | Sneakers | Similar Bag

18. Black midi dress with brown sandals and belt bag

I love this dress for traveling when you want a piece you can dress up or down. I included this look in my post, 12 Easy Stylish Summer Travel Outfits + Packing List. This leather belt bag is elevated and holds your most essential items. Brown ankle wrap flat sandals are perfect for strolling the streets and dipping into museums or a cafe for a coffee or leisurely lunch. 

 Black midi dress with brown sandals and belt bag

Dress | Similar Sandals | Similar Bag | Hat

Infographic shirt dress outfit ideas

Hi, Friend. I'm Marya. I'm so glad you're here!

I’m here to help women feel good inside and out through approachable everyday style inspiration and encouragement for midlife. Once upon a time, I worked as a therapist and coach. Now, I’m a holistic style blogger studying style coaching! Be So You celebrates leaning into who we were meant to be! 

Read about my  journey to self-discovery at 40. Follow me on Instagram here and Pinterest here. Send me a quick question through my contact page here.  

Fit Note: I’m midsized at 5’6″, 160 pounds, with size 12 jeans.

You might also like...

Leave a Reply

Your email address will not be published. Required fields are marked *

Free Download - Human Design for Midlife Women

Get the Quickstart Guide to Human Design for Midlife Women

Short Description

Your privacy is important to me. That’s why I collect, use, and process your personal data only in accordance with my Privacy Policy. You may unsubscribe at any time.