15 Simple Ways to Wear Shirt Dresses (Outfit Ideas)





Last Updated: October 12, 2021

With the seasons changing and the weather shifting, everyone is moving toward a new dress code. Gone are the days of heavy sweaters and denim jeans. Instead, it’s time for shorts, skirts, and summer dresses, which includes the shirt dress.

The shirt dress is a garment that has been around since the 1930s, but has seen a resurgence in the past few years for its simple and casual style. It is often considered to be a more “casual” version of a dress and something you don’t have to put as much thought into when getting ready in the morning.

However, for some this trend can seem a little intimidating. Shirt dresses don’t have much of a shape and can sometimes box individuals in if they aren’t sure where to start with styling.

Though it may seem like a leap, there are many different ways to wear shirt dresses in order to fit your aesthetic and feel cute and comfortable all summer long. Keep reading to find the best shirt dress outfit ideas!

How to Wear Shirt Dresses

Wear With Heels

Though it may seem counterintuitive for a more casual piece of clothing, shirt dresses can be easily dressed up to create a more elegant, yet effortless look. Throw on a pair of heels, a bag, and a red lipstick to create an outfit for a night out that would make anyone jealous.

For a more daytime, but still dressy look, opt for a pair of booties instead of heels and throw a jacket over the dress. This look will still show effort but will be a little more calm for going about your day-to-day activities.

Note: Picking an elegant satin or silk shirt dress will make dressing it up easy!


Pair With Sneakers

For some people, comfort is the epitome of style and shirt dresses can offer exactly that luxury. If you still want to add a little bit of flair into your more casual daytime look, you can wear your shirt dress with a pair of white sneakers and some high rise socks or a backpack to finish the ensemble.

If you have somewhere to be but still want to get there in style, this is a perfect way to make a statement with your outfit.


Wear Off The Shoulder

Shirt dresses are often considered a “running errands” type of a garment, but they definitely do not have to fall into this category. Amp up the sexiness of your dress by finding one that has off the shoulder sleeves or by creating an off the shoulder effect yourself.

This little touch to your outfit will add just enough edge and spunk to show others you have a little flair while also staying simple.


Wear With A Jacket

Everybody knows a good jacket can completely make a look, and the same goes for shirt dresses. If you feel your outfit is a little too simple, throw on a leather bomber or a denim jacket to spice things up.

This option is also perfect for cooler days when you still want to rock a cute little dress.

RELATED: How to Wear a Leather Jacket – 12 Outfit Ideas


Wear With Sandals

Summer is the time everybody wishes they were at the beach, so why not act like it?

If you want to add a fun twist to your shirt dress, throw on some sandals and a cute sun hat to create a day at the beach aesthetic that would brighten up anyone’s day.


Wear Over Jeans

While some individuals may think dresses over pants is a bit too 2000s for their liking, it can be a fun way to wear shirt dresses. If you want to go for a more decades inspired feel, opt for flared or bell bottom jeans underneath your shirt dress for a more free spirited look.

However, if you want your look to feel a little more polished and put together, opt for leggings or narrow-legged jeans. This will offer you more coverage with the dress but still give you a fun, summery effect.


Wear With Combat Boots

If your style tends to lean a little more edgy than fun and flirty, shirt dresses can still be an option within your wardrobe. Throw on some accessories like combat boots, a choker, or fishnets to make your outfit stand out from the crowd.

You can also opt for a darker toned shirt dress in order to match the rest of your aesthetic and make sure your look matches the rest of your wardrobe.


Wear With A Blazer

Oftentimes, people think that blazers can only be for the work environment, but that is definitely not the case. If you want to pull together a slightly more mature look, throwing a blazer over your shirt dress and hanging a bag at your side can give the illusion that you are running all sorts of important errands.

Whether you are a busy business woman or simply just living your day-to-day life, there is no reason why you can’t throw on some more “adult” accessories. Wearing a blazer will give you an aura of confidence you never thought possible.


Put A Belt Over It

One of the most common worries with shirt dresses is that they will make you look boxy or take away your figure. Though this keeps some individuals from wearing this particular garment, it is also a fear that can be easily stopped.

If you are somebody who is afraid to wear shirt dresses due to it dropping your figure, try using a belt accentuate your shape. Wearing a belt across the middle of a dress is always a perfect way to add a little bit of personality and flair to an outfit while also emphasizing all your assets.


Roll Up The Sleeves

Some days you want to feel a little more playful and casual than others, and a shirt dress can accommodate for all of those times. If you want a more simple and casual outfit, throw on a shirt dress and roll up the sleeves to give a more “minimal effort” effect.


Choose An Open Neckline

A common misconception about shirt dresses is that they are a more frumpy version of a regular dress. While this may seem like the truth, there are many little steps you can take to make a shirt dress more appealing to those who don’t like to dress conservatively.

Open a few buttons in the front or opt for a shirt dress without a collar in order to have a deeper neckline. Play with the style to find something that fits who you are.


Pair With A Sweater

Many individuals completely write dresses out of their wardrobe once the cooler seasons hit, but it is important to remember that you can add dresses into your wardrobe even if the temperatures dip.

Throw on a sweater over the top of your shirtdress or tuck it into a pair of high waisted pants to turn it into a cute top instead that will also be slightly more weather appropriate. One of the best aspects of shirt dresses is their ability to DIY into something slightly different in an instant.


Choose A Fun Pattern

Many shirt dresses often come in fun colors or patterns which can be a perfect addition to any individual’s wardrobe, especially for the summertime.

Mix up different prints to create a look that is unique and fun but still fits your personality. Dresses can be especially easy to play around with because they are only one piece and generally simpler to style.


Pick Plaid

While many think of flannels as being only a fall time look, plaid is a pattern that can work for any season and can be used to create a fun and fashion forward look. 

Take a brown or black belt across the middle of a plaid shirt dress to add a more dressy feeling to the outfit and to also add a little more shape to the silhouette.


Wear As A Midi Dress

If you are somebody who tends to steer clear of shorter dresses, that is no reason to stay completely away from shirt dresses. There are several length options when it comes to shirt dresses, so you are bound to find something you will feel comfortable in.

Instead of opting for a mini shirt dress, try to find one that is midi length that will fall more around your knees. These can be a fun and whimsical version of a shirt dress that can offer you a little more comfort in the style.


To Sum Up

Shirt dresses can sometimes be an intimidating outfit in one’s wardrobe. Though they may seem like an easy piece to wear, there are so many ways to style them that it can almost feel overwhelming.

However, with so many options to play around with, you are sure to find ideas on how to wear shirt dresses that can suit any of your needs.