10 Easy Shoe Styles To Wear With A Shirt Dress

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Shirt dresses are a great choice for a range of occasions; here’s our guide on the best shoes to wear with your dress to make the most stylish outfits!

Shirt dresses have been a long-standing classic choice of the chic women of the world. It’s pretty self-explanatory, a shirt that continues past the waist into a dress. A shirt can be difficult to style or ends up creasing throughout the day. However, a shirt dress is an effortless and comfortable way to still look put-together for formal or work-related events.

Their history traces far back to the 1920s – to a time when the Masculin Féminin style was taking the fashion world by storm. Of course, this was at a time when women’s fashion was fairly monotonous – and not as risque as now – so they were still only worn with low-heeled shoes – luckily, we have plenty more options now!  During World War II, when textiles were in short supply, simple styles, which would consume less fabric, were favored, though styles at this time looked closer to those of a uniform than a sartorial statement. 

Reformation Shirt Dress Styled with Black Strappy Flats
Get this dress on Reformation

It was only after the war that luxury brands like Christian Dior created their own take on the shirt dress, one which is still popular at the brand. Today, the shirt dress remains a popular and versatile garment. It can be found in various styles, lengths, and fabrics, catering to different fashion preferences. Its enduring appeal lies in its ability to transition from casual to formal occasions effortlessly, and from the summer to winter months, making it a wardrobe staple for many women.

These traditionally were only available in a classic cotton a-line silhouette; however, they now are available in all fabrics, colors, lengths, and for all occasions! You can find cotton shirt dresses that suit daytime formal events or silky short shirt dresses that suit a beach club party! Owed to their versatility, though, shirt dresses are really able to be accessorized to fit any occasion – which is exactly why choosing the correct footwear is of the utmost importance.

With so many shoe options available, it can be difficult to know the right shoes to match your shirt dress and how to style your outfit. But good news! As always, we’ve done the research, so you don’t have to, and below, you’ll find our list [complete with styling options] of the ten best footwear options to wear with a shirt dress.

What Shoes To Wear With A Shirt Dress

1. Flat Sandals

Flat shoes are a great option for down your shirt dress, especially when you’re on vacation or for a more casual look. This shoe style will pair very well with a linen or cotton dress for the daytime.

If you like a minimal look, a pair of tan or black sandals paired with a simple white shirt dress will make a perfect casual outfit. To dress it up or to add some shape if it lacks a defined silhouette, add a chunky belt that matches the color of the shoes.

They’re perfect for adding a casual vibe to your outfit, but you can also opt for sandals that are fancier for an effortlessly cool summertime look, like a pair which are heavily embellished or a bright color.

flat sandals we love
Prada Ciabatte Clear Flat Sandals

Ciabatte Clear Flat Sandals

At Neiman Marcus

See by Chloe Tan Hana Thong Sandals
See by Chloe

Hana Sandals

At Revolve

Cult Gaia Yellow Milo Sandals
Cult Gaia

Milo Sandals

At Cult Gaia

2. Sneakers

If sandals aren’t your thing, sneakers are a great way to keep your look dressed down and comfortable while still being sophisticated. You can opt for a pair of classic white sneakers or platform sneakers, available from all of your favorite designer brands.

Shirt dresses are often made in natural materials like linen and cotton, making them great summer dresses. Though for the colder weather, if you’re permitted to wear a pair of sneakers to work but still need to keep the overall look elevated, a trench coat is the perfect addition to your outfit and fall wardrobe!

Rag & Bone White Retro Court Sneakers
Rag & Bone

Retro Court Sneakers

At Revolve

Veronica Beard Valentina Genuine Shearling Lined Sneakers
Veronica Beard

Valentina Shearling Lined Sneakers

At Nordstrom

Alexander McQueen White Oversize  Gold Eyelet Sneakers
Alexander McQueen

Oversize Sneakers

At Nordstrom

3. Espadrilles

It only feels fitting to focus on summer styling options for the time being! Espadrilles – whether flat or wedged – are the perfect shoes to style with shirt dresses. Espadrilles date back to the times of the Romans and the Greeks and are extremely hardwearing shoes.

An iconic espadrille brand famed for making the ‘wedge,’ well, famous, is Castañer. This Catalonian brand was tasked by Yves Saint Laurent in the 1960s to make the wedge for the brand, given that the artisans were skilled with using the role-like material.

As for the rest of your laid-back look, a sun hat or bucket hat will pair well with a cotton shirt dress, whether long or short! And if it’s chilly – a denim jacket is a summer staple you need during the spring-summer months.

Chloe Piia Embroidered Logo Denim Espadrilles

Piia Embroidered Denim Espadrilles

At Neiman Marcus

Saint Laurent Signature Espadrilles
Saint Laurent

Signature Espadrilles

At Nordstrom

Larroudé Naomi Flatforms

Naomi Flatforms

At Revolve

4. Block Heels

Block heels are a good choice if you still need a shoe option for a formal event to pair with your shirt dress but need something more comfortable than the heel height of a stiletto, which though beautiful – isn’t suitable for every occasion.

Block heels can provide some stability and are suitable if you’re likely to be standing and mingling or if the event is on grass which your stilettos would sink into; we’ve learned this one the hard way! Block heels are also available in funky designs owed to the extra space on the heel – we’ve added some of our favorite crazy options!

These would be best paired with a maxi or ankle-length shirt dress, as the low heels will provide some height while not being too high and creating odd proportions.

Silver crystal slingback shoes

CC Logo Slingbacks With Crystals

At Chanel

Badgley Mischka Feisty Pearly Satin Block-Heel Sandals
Badgley Mischka

Feisty Pearly Block-Heel Sandals

At Neiman Marcus

Chie Mihara Cage Sandals
Chie Mihara

Cage Sandals

At Nordstrom

5. Ballet Flats

We’re saying ‘oui’ to the Parisian-favored ballet flats! Don’t be under any misconception; even with two left feet, you can rock these all day and night!

Ballet flats are one of the oldest flat shoes to enter the women’s garments world, with references being seen in 17th & 18th-century fashions. With the resurgence of the shoe in the recent ‘ballet-core’ micro trend, the shoe is only getting more popular!

If you prefer a super feminine look, a shirt dress can look almost regimental, and ballet flats will soften the look. You can either opt for something nude and classic if you prefer neutral colors or use the opportunity to add a pop of color.

Roger Vivier Gommettine Fringed Denim Ballerina Flats
Roger Vivier

Gommettine Denim Ballerina Flats

At Neiman Marcus

Gucci T-Strap Ballet Flats

T-Strap Ballet Flats

At Nordstrom

Christian Louboutin Mamadrague Cotton Red Sole Ballerina Flats
Christian Louboutin

Mamadrague Ballerina Flats

At Neiman Marcus

6. Knee-high Boots

Green Satin Shirt Dress Styled with Dark Brown Knee High Boots
Get this on Moda Operandi

Knee boots are great if you want to wear a shirt dress during the colder months. The silhouette of most shirt dresses means the cold winter air will likely affect you if not styled properly.

Not only are taller boots a great option during these cold months, but they also add a ‘countryside chic’ elegance to your look.

You can pair this with a classic pair of riding-style boots or the newly popular cowboy boots capturing the fashion crowd. To complete the look, a leather jacket will make this look youthful, or a camel coat to make it more formal.

Schutz Maryana Croco Stiletto Knee Boots

Maryana Croco Stiletto Knee Boots

At Neiman Marcus

Schutz Maryana Block West Boots

Maryana Block West Boots

At Revolve

Paris Texas Silver Croco Metallic Stiletto Knee Boots
Paris Texas

Croco Metallic Stiletto Knee Boots

At Neiman Marcus

7. Stiletto Heels

Stiletto heels are the perfect choice for dressing up a shirt dress. They add glamour and elegance, and a pair of nude heels can make you appear taller with longer legs!

It’s even said that wearing a pair of heels can help you stand taller with better posture, perfect for work occasions when you need to stand tall and confident.

Pair your shirt dress with pointy heels for a work event or strappy heels for a night out on the town! For a smart look, dress down your accessories. While you can wear chunky jewelry and a statement clutch for a fun, dressed-up outfit!

Amina Muaddi Begum Glass Pointed Toe Slingback Pump
Amina Muaddi

Begum Glass Pointed Toe Pumps

At Nordstrom

Gianvito Rossi Metallic Napa Ankle-Cuff Stiletto Sandals
Gianvito Rossi

Metallic Napa Ankle-Cuff Sandals

At Neiman Marcus

Alias Mae Green and Pearl Bowie Heels
Alias Mae

Bowie Heels

At Revolve

8. Combat Boots

Classic Blue Shirt Dress styled with combat Boots and White Shirt
Get this on Net-A-Porter

Combat boots are a great option for dressing up or down a shirt dress. If your personal style is edgy, but you need to look smart for a particular occasion, this can be a great way to combine both aesthetics.

Combat boots are derived from the footwear worn in combat [if that wasn’t obvious]. They were heavy with a chunky rubber sole and made to carry their wearer through the difficult conditions of the war. Later, they became associated with the punk movement in the 1970s – symbolizing non-conformance with societal norms. 

While chunky boots are a classic today, and a must-have in every autumn-winter wardrobe, consider still making them look softer by pairing them with a smart coat and light-colored shirt dress.

ALLSAINTS Black Donita Boots

Donita Boots

At Revolve

Naked Wolfe Black Sloane Leather Platform Combat Boots
Naked Wolfe

Sloane Leather Platform Boots

At Neiman Marcus

Aquatalia Black Croc Embossed Wedge Combat Boots

Croc Embossed Wedge Boots

At Nordstrom

9. Ankle Boots

Ankle boots are another great option for dressing up or down a shirt dress. They add elevation and personality to your entire look. They are also great if you need to dress up your outfit for the evening but don’t like to wear heels or aren’t appropriate, such as for a concert or music festival.

While you can wear ankle boots with any color of shirt dress, it would be a good idea to be mindful of the length of it.

If paired with an ankle-length dress, there is the possibility of the overall outfit looking frumpy and unflattering. Instead, opt for a mini or knee-length dress to show off your boots!

Jeffrey Campbell Gold Shiny Rancher Boots
Jeffrey Campbell

Rancher Boots

At Revolve

PAIGE Porter White Leather Western Ankle Booties

Porter Leather Western Ankle Boots

At Neiman Marcus

Alexander McQueen Silver Pointed Metallic Punk Buckle Booties
Alexander McQueen

Metallic Punk Buckle Booties

At Nordstrom

10. Loafers

Short Sleeve Linen Beige Shirt Dress styled with woven loafers and raffia bag
Get this on Net-A-Porter

Last but not least – loafers! These are as formal as a shirt dress and will pair very well if you have a more formal occasion or need a closed-toe shoe to wear during a hot day. 

If you were looking for a pair to wear to work, a classic pair of black loafers will be suitable for everyday wear. If you need a casual [but still chic] everyday shoe, luxury brands have some fabulous colorful loafers and moccasins.

Loafers, if styled incorrectly, can look dowdy. Be mindful of the time of day and occasion. Many color and fabric variations are now available, meaning you can find an option to pair with a shirt dress for any daytime occasion.

Rag & Bone White Sid Woven Loafer
Rag & Bone

Sid Woven Loafers

At Revolve

ST. AGNI + NET SUSTAIN macramé leather loafers

+ NET SUSTAIN Macramé Loafers

At Net-A-Porter

Gucci White Princetown Loafer Mules

Princetown Loafer Mules

At Nordstrom

We hope this style guide has helped give you some ideas about the best style shoes to wear with your favorite shirt dress!

As always, we hope to act as a guiding star rather than a fashion dictator, be sure to experiment with different combinations until you find the perfect look for you. And the most important styling tip is always to feel confident in whatever you choose to wear!

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