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Shirt dresses are a wardrobe staple that you can pull out, throw on and always trust in when it comes to creating the perfect outfit. Since the 1950s, they have been one of the coolest pieces, and they are now a timeless must-have for all fashionista. They are also very versatile, so they can be used as a transition piece from your usual work attire to a more formal look.

Although they are usually considered summer perennial, there are many ways to style your shirtdress even in the coldest season. You can finally use your favourite dress every time you want to!

We are here to show you the many ways to rock your shirtdress whatever the weather and make each piece in your wardrobe a versatile ally for all your looks.


What Is A Shirtdress?

A shirtdress is a type of dress that resemble men’s shirts. These pieces include a collar, cuffed sleeves and a button front. Besides, they are usually made up in cotton, silk, or denim, just like standard shirts.

Shirt dresses have a looser fit, and they are cut without a seam at the waist. You can make them more tight-fitting, for an extra slimming effect, with a simple waist belt.

Although these dresses are very cute and stylish, they might not be particularly flattering for certain body types. Curvy girls or those who don’t feel comfortable with oversized and bulky looks should avoid these dresses or only style them with more accessories.

The History of Shirt dresses

Shirt dresses made their appearance in the 1950s, and they were originally known as shirtwaist dresses. Allegedly, the first model was created by Christian Dior as part of his “New Look” couture design. The first shirt dress was made of a full skirt held up by a crinoline.

In 1957, Life magazine featured the first picture of a shirt dress for sale. The look immediately became iconic, inspiring streetwear designers and all fashionistas around the world.

The shirt dress even inspired the “T-shirt dress”. As the name suggests, this is an elongated version of a T-shirt, which is intended to be more casual than a shirt dress.

How do you wear a long shirt dress in the winter?

Shirtdresses are usually a summery piece, but you can still rock them in winter. For example, you can top your shirtdress with a coat or even a fur coat. Make sure to use different lengths, especially if your dress is particularly long.

How to wear a shirt dress to work?

Wearing a shirtdress to work can be the perfect idea to rock a unique office outfit. To make it look great, you can add some sneakers or sandals, and a comfy big bag. Black dresses are usually perfect for looking chic but not overdressed.

Dark Shades Are More Wintery

We tend to associate dark colours, such as black, to the cold weather. This means that you can wear a dark shirtdress even when it is snowing out there. This is how you could style it:

  • A black leather jacket.
  • A woolly baker hat.
  • Some suede over the knee boots.

Long Coat, Long Dress

If you are a tall girl and you like to play with different lengths, then you should definitely try this look:

  • A long shirt dress in a nude colour.
  • A patterned and colourful coat. It should be shorter than your dress, ideally hitting the wider part of your hips.
  • A matching wintery bag and some loafers.

Also Read:

What to Wear with An Overall Dress in Winter (Women’s Edition)

How to Layer A Turtleneck or Pullover Under Your Dress Outfit Ideas (Women’s Edition)

How to Wear A Combat Boots in Winter – Outfit Ideas & Styling Tips (Women’s Edition)

Total White Style

White is the colour of snow, so it makes perfect sense to wear it to welcome winter. Total white shirt dresses might be tricky to wear, so we recommend pairing them with only a few accessories and wearing them as they are. If you don’t feel comfortable with wearing white, you can experiment with other nude shades.

Full-Length Pieces

Yes, tights are great and cosy in winter, but you don’t necessarily need to wear them to keep your legs warm. For example, you can rock a floor-skimming shirt dress, which will cover your skin and protect you against the cold wheat. Wear some heeled shoes to elongate your silhouette.

Layer It Up

Have you ever worn your trousers under a shirtdress? This combination may sound odd, but this is one of the most trending styles among celebrities.

  • Make sure your dress colour matches your trousers
  • Ideally, you should opt for skinny leather pants
  • Wear a formal pair of trousers for a contemporary workwear outfit.

Denim Is Cool

Denim is a cool fabric, and it is very versatile. Although many prefer to wear it in spring or summer, you can definitely style it even if it’s snowing. For example:

  • Wear a midi denim shirtdress, with long sleeves to keep you warm.
  • Wear some tights if you want.
  • Add some suede ankle boots to make the whole look more wintery.

Welcome Winter with Some Accessories

Accessories can really change your look, even if you are wearing a simple shirtdress. For example:

  • Beanies, fedora hats and baker hats are perfect for any cold season
  • Drape a lightweight jacket over your shoulder for an autumnal outfit
  • Wear a bulky scarf for a statement look

A Jacket Can Save Your Day

Sometimes, all you need is a transitioning piece to wear your shirtdress and still be prepared in case the weather turns too cold. No worry, you can always rely on your jacket!

  • Suede and leather jackets are perfect in late spring or autumn.
  • If you are feeling bold (and cold) wear a teddy coat.
  • The jacket shouldn’t be longer than the dress.

More Layers Are Better Than One

Layering more clothes is always the best secret when it comes to wintertime outfits. For example:

  • Wear a sweater over your shirt dress.
  • Opt for contrasting colours (for example, black and white).
  • Match your accessories to the outfit’s colour palette for the best result.

Over the Knee Boots

If you don’t want or need to wear a jacket, there are other ways to make your shirtdress more wintery. One of our favourites is over the knee boots. These shoes are perfect to keep your lower body warm, and they look great with all styles.

Oversized Turtleneck Sweaters

Turtleneck sweaters are some of the most beloved wintertime pieces by many fashionistas. To play with these tops, you can:

  • Layer an oversized turtleneck top over your shirtdress.
  • If you decide to stick to a single colour or shade, add a touch of colour with some stylish thighs.

Oversized Shirt dresses

Since they are long and bulky, oversized shirt dresses are usually considered adequate wintery outfits. However, you should avoid these pieces if you prefer to create a thinner and slimmer silhouette. Otherwise, you can try them with:

  • A pair of combat boots
  • A small bag or other minimal accessories


Black leggings are a must-have for all wintertime wardrobes. Ready to style your leggings with a shirt dress?

  • Try a pair of black full-length leggings with a white shirt dress.
  • Add a bright accessory, such as a yellow waist belt.
  • Match your shoes with your leggings.
  • Add some oversized sunglasses to protect your eyes.

Shirt dresses And Jeans

Just like leggings and other pants, jeans work perfectly with a shirtdress, especially if they are skin-tight. Our words of advice:

  • Feeling bold? Match a pair of jeans with a denim shirt dress!
  • Oversized dresses also work beautifully with this style but don’t forget to add a few accessories.
  • Avoid boots or any type of chunky footwear.

About The Author

May is totally crazy about the 80s and everything the decade inspired! Having grown up in a household that was totally taken over by 80s music and fashion its only natural that May lives and breathes the 80s!

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