8 Shoes to Wear With a Shirt Dress
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  • Writer's pictureBrenda

8 Shoes to Wear With a Shirt Dress

Updated: Feb 13

A shirt dress is one of those clothing items I turn to when I’m either PMS-ing, bloated or unsure of what to wear that day. After my myomectomy, I was living in shirt dresses for the first few weeks because they were so easy to slip on, hid my belly and did not rub up against my scar.

I think you could say I became somewhat of a shirt dress expert during the two months I was recovering at home as I knew which shirt dresses to wear at home, which ones to wear to my doctor’s appointments and which ones were best to wear on a walk.


A lot of women tend to wear shirt dresses when they want to feel most comfortable or if they are trying to hide their belly (which could be due to weight gain or a baby bump). No matter your reason for wearing a t-shirt dress, it’s always great to know how to style it depending on where you’re headed to.

For today’s blog post, I would be sharing different ways to style a shirt dress for different occasions. You’ll come to see just how easy it is to put together a chic shirt dress outfit using pieces you most likely already own. The styles would be similar to those mentioned in my post on how to wear a high-low dress.

One of the things I love the most about shirt dresses is how they tend to come in one size fits most. This allows me to wear the same shirt dress for years, regardless of weight fluctuations.

Another characteristic of t-shirt dresses which I love is how easy it is to style them up or down. Most times, a belt and a pair of high heels are sufficient to take your shirt dress from dog park to date night.

Before I jump into the various outfit ideas you can use as a guide, I would like to share some of my favorite shirt dresses currently for sale which you need to check out if you’re looking to add a couple to your wardrobe.

*Disclosure: This post may contain affiliate links, which means that I get a small commission if you decide to make a purchase through the links, at no cost to you.

Types of shirt dresses to own

- Corporate shirt dress

I’m a firm believer in having multiple types of shirt dresses and the first on this list is this poplin shirt dress which you could be a great option wear to the office. You could wear it with a pair of leggings underneath and with or without a trench coat for a complete corporate look. I love how the model’s look was styled with a scarf around the neck and so you could use the same style tip.

- A fitted white shirt dress

There’s something so feminine and sexy about a white shirt dress that’s more fitted at the waist. Not only would it give you a more hourglass figure and flattering waist, but it’s also very easy to style. You don’t need much to complete your look except for a pair of shoes and a small purse. This long-sleeved shirt dress is an excellent choice to easily do the trick.

- A shirt dress in a bold print

You can make your shirt dress stand out by opting for one in a bold print. This works great for a night out where you don’t want to wear tight clothing but still want to look stylish. This zebra print shirt dress for example would loke great with some ankle boots or open-toe heels.

- A short sleeve shirt dress

Short-sleeved shirt dresses make for the base of a great laid-back look. You could style these with flat sandals or a pair of white sneakers for a quick grocery store run. What’s great about them is you could pair them with a pair of thigh-high boots and a jacket to create a look worthy for date night at the movies.

This Lululemon shirt dress comes in various colors and would be a great way to achieve this classic style.

- A dressy shirt dress

I love how shirt dresses now come in very elegant style that you could wear for a formal event. I’ve been eyeing this balloon sleeve midi shirt dress. Style it with strappy sandals and an evening clutch for either a birthday dinner or formal gathering. The front ruching on the dress is also very flattering on women with a little extra weight in the mid-section.

Now that we’ve gotten our core shirt dresses down, let’s talk about styling them in different ways. Regardless of your body type, you would be able to pull off multiple if not all of these looks. You can click on the images as well to shop these looks if you’re interested in purchasing any of them.

1) Shirt dress with sneakers

A pair of white sneakers are the perfect shoes to go with a casual shirt dress. You know how much I love my white sneakers over any other color because they just make any look appear fresher without trying. You could try this look with either a mini or maxi white dress to achieve the same look. To make this look more formal, add a pair of black leggings, a belt and a pair of heels.

Get the look HERE

2) Shirt dress with ankle boots

During the cooler winter months, a shirt dress could be layered upon to create a warm and chic winter look. Consider wearing a light sweater or tank top underneath your shirt dress and then adding a pair of leggings as well for extra warmth. Next, you could add a plaid shacket or cardigan in a neutral color on top to complete your cold weather look.

If it’s still early fall, you could just wear a denim jacket on top of your shirt dress and you’ve got yourself a cool Fall look.

Get the look HERE

3) Shirt dress with over-the-knee boots

I love a good knee-high or thigh-high boot in the Fall and wish I could pull it off more but unfortunately my larger calves will not allow me to live my best high boots life. A great way to rock a shorter shirt dress during the colder months is by adding a pair of higher boots and even a black leather jacket to your dress.

If your shirt dress is really short, feel free to add a pair of black skinny jeans or leggings underneath for a great look. You can also opt for an oversized sweater look like this one.

Get the look HERE

4) Shirt dress with combat boots

Although combat boots are a type of ankle boot, I wanted to give them their own shine because they could be worn to create a more casual look. I find them to lend a more youthful vibe to any outfit and so I encourage you to try them with your shorter shirt dresses. You could also wear a shirt sweater dress with some combat boots and you would be rocking a cozy yet stylish Fall outfit. I’m loving the chocolate shirt dress below.

Get the look HERE

5) Shirt dress with flat sandals

A more casual look you can rock during the warmer months is a shirt dress with flat sandals. This could be worn for a day on the beach, a trip to the coliseum or to a local café on a warm Summer day. Flat shoes are always a good choice when you don’t feel like struggling with a pair of heels. A midi, mini or maxi dress could work with this type of shoes. Just accessorize with a shoulder bag and you’re all set.

Get the look HERE

6) Shirt dress with strappy sandals

Strappy heels are the perfect way to elevate a shirt dress. They’re the best shoes to really work that dressy shirt dress when you’re styling it for a special occasion. If you want to flaunt your legs, opt for a shorter type of dress. Feel free to play around with colors as there are only two main items in your outfit – the shirt dress and your heels.

You could definitely go with a shirt dress in a neutral color and even create a monochrome look by matching your heels to your dress.

Get the look HERE

7) Shirt dress with mules

Mules and shirt dresses make for a perfect match because they’re easy to slip on while making your legs appear longer. That’s why I recommend wearing them with your shorter shirt dresses. They help to create a more formal look without the hassle of strapping anything on.

Get the look HERE

8) Shirt dress with flats

A pair of ballet flats can be worn with a shirt dress for either an office look or for everyday wear. A great way to create a cute casual outfit with the shirt dress trend in mind would be to pair a denim shirt dress with a pair of ballet flats and a tote bag. Black shoes would work great with this outfit thanks to their neutral color but you could also try white shoes if you’re feeling a little bright.

Get the look HERE

As you can see, it’s incredibly easy to style shirt dresses and they truly come in different styles and lengths. If your shirt dress is oversized and you’re feeling lost in it, add a belt on top to emphasize your waist and some chunk jewelry to bring attention to your face rather than your body.

The kind of shoes you choose to wear with your shirt dress depends on the look you’re going for. The best shoes to go with shorter dresses are taller boots, high heels and mules while longer shirt dresses look great with ankle boots, heels, flats and wedge heels.

If you enjoyed this post, I recommend you check out my post on how to wear a high low shirt.

I also have a post on 5 ways to wear a high low skirt, which can be styled in similar ways to a shirt dress.

Looking for what to wear for Easter? Check out my post: 10 outfits to wear to stand out this Easter.

Until the next post,



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