How to style a shirt dress by celebrity stylist Gemma Sheppard

Working out how to style a shirt dress will help to add versatility to your wardrobe

Gemma Sheppard and a model in a shirt dress: How to style a shirt dress
(Image credit: Gemma Reynolds / Future)

With summer is in full swing, learning how to style a shirt dress should be high up on your agenda. A wardrobe essential that can be worn day-to-night, beach-to-bar. It’s the perfect item to reach for on “I don’t know what to wear” days.

The earliest shirt dresses date back to the Victorian era when they were then known as shirtwaist dresses (shorthand for what we now know as a blouse) but it was Christian Dior who made shirt dresses iconic when, in 1947, he brought a ‘new look’ to womenswear - a more feminine version of a man’s shirt (standard collar, button front, sleeves) and by the 1950s, the shirt dress was a fashion staple across the world. 70 years on and the style is as popular as ever, with the likes of Meghan Markle just one of several stars nailing how to style a shirt dress on multiple occasions. 

Shirt dresses are the perfect addition to your capsule wardrobe and straight-to-market stores such as Cos, Zara and Mango bring out variations in different fabrics and patterns every season, so you’ll always find a style that suits you. Whether you’re creating an outfit for the office, lunch with friends or sightseeing; you’ll find a shirt dress in an array of colors and patterns to meet your brief. While the trappings of the best shirt dresses might change with seasonal trends, the fundamentals of the design remain the same, making it one of the best dresses to invest in. 

How to style a shirt dress 

Celebrity stylist Gemma Sheppard takes you through how to style a shirt dress this season. From weekend casual to smart work attire and everything in between, whatever your size or height we've got a shirt dress for you. 

1. How to style a shirt dress for work

three women in work appropriate shirt dresses

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When it comes to summer outfits for work a shirt dress should be top of your list. The shirt design gives your look added polish, thanks to the tailoring aspect, while the dress silhouette adds a more feminine feel to your overall look. Opt for linen and cotton iterations as they're two of the best fabrics to invest in when deciding what to wear in the heat

A sturdy investment piece, while shirt dresses are ideal for the spring and summer season, they'll work in cooler months too. On chillier days layer a cardigan or your best blazer over the top of your shirt dress, or wear a slim fit, fine knit or roll-neck under your dress for a cozy but smart finish.  

2. How to style a denim shirt dress

three women in denim shirt dresses

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Denim aficionados will know that the denim trends 2022 hailed the return of the denim dress and the shirt dress was at the forefront of the look. As effortless as your best jeans, denim shirt dresses manage to combine cool and casual with just a hint of androgynous styling for an outfit that will always look directional. While darker denim iterations will add polish to your look, light wash and light weight designs will err on the side of more casual.

3. How to style a shirt dress for weekend casual

three women in casual shirt dresses

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Thanks to its more tailored design, learning how to style a shirt dress for the weekend is something of an artform, the key, however, is all in the accessories. Lean into a more relaxed look by opting for a shirt dress that's slightly looser - mimicking a man's shirt. To draw attention back to your silhouette, add a slim tie belt, that feels more nonchalant than a buckled design. Opt for classic accessories such as a pair of trainers or a summery pair of espadrilles to get you weekend ready. 

4. How to style a shirt dress for an occasion

three women in occasionwear shirt dreses

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Still searching for what to wear to a wedding this summer? Shirt dresses make for some of the best wedding guest dresses as they pair together tailoring and femininity for a flattering finish. To learn how to style a shirt dress for an occasion, look for luxe fabrications and great prints that will elevate the style from everyday wear to party-ready attire. Investigate how to wear a hat with your shirt dress if your event this season requires one.

5. How to style a shirt dress with trousers

shirt dresses with trousers on three women

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Another way to wear your shirt dress is over loose-fitting trousers. An ideal look to pack for a summer vacation, this chic pairing is a winning holiday outfit idea as it adds versatility to your existing wardrobe and helps to create a capsule edit when traveling abroad. 

To style a shirt dress with trousers, layer your shirt dress over a vest top or camsiole and wear the dress completely unbuttoned (like you would a kaftan). Tuck a slouchy bag under your arm and add a kitten mule for an effortless day to evening look.

You can also forgo the vest top and wear your shirt dress buttoned to the waist, before leaving it undone and worn over a pair of wide-leg or palazzo shaped trousers. This style works particularly well with linen and cotton designs and the shirt dresses should be relatively straight in cut and ideally midi, midaxi or maxi length. 

6. How to style a shirt dress as a beach cover up

three women at miami swim week on the beach runway for Acacia fashion

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One of my favorite ways to style a shirt dress is as a beach cover-up! Smart enough that you won’t feel out of place if you go for lunch or a post-beach cocktail, a button through shirt dress done up fully or partially is a great option for chic poolside style. Look for less tailored silhouettes, or oversized designs so that it feels relaxed and effortlessly thrown together. 

7. How to style a maxi shirt dress

three women in maxi shirt dresses

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Maxi lengths conjure up instant glamour, with big silhouettes the name of the game when it comes to this style. Taking its lead from the Fall 2022 fashion trends - full skirts are back and this shape is balanced almost entirely by an emphasise on the waist. Make sure your maxi shirt dress features a dramatic A-line and high- waist cinching belt to nail the look. Remember, to add polish to your outfit, swap self-fabric belt designs for wide, wrap obi iterations, or statement buckle belts to really highlight your curves. 

8. How to style a plus size shirt dress

three women on the runway: Christian Siriano / Lane Bryant / Addition Elle / Melbourne Fashion festival

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When it comes to the best plus size dresses, a shirt dress is a great cut for a fuller figure. While you can go for oversized fits, these can have a tendency to add bulk to your frame, where as A-line and fit and flare variations are some of the most stylish dresses to hide a tummy, as they contour your frame, nip in at the waist, before flaring out over a midriff.

As a shirt dress will have a button front, make sure to really consider fit, as the last thing you'll want is buttons that gap and leave you tugging at your clothes. A smart and tailored design, look to the best plus size clothing brands that will accommodate larger bodies. 

9. How to style a shirt dress for petites

three women in petite shirt dresses

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If you’re petite, to ensure a shirt dress doesn’t swamp you, choose a shorter length that can be cinched at the waist. Petite ranges are designed for women who are 5”3’ and smaller so the cut will be shorter on the torso and arm length - giving you a better overall fit. For the best petite dresses, it is always worth looking at department stores or online sites that stock petite specific categories. 

Keep your accessories smaller too. Instead of a huge handbag, which will look will out of proportion, an on-trend mini bag will fit the essentials without overpowering your look. When choosing footwear, a flatform will give you extra height whilst ensuring maximum comfort.

Gemma Sheppard's must-haves

Gemma Sheppard is an international fashion stylist with a successful consultancy business working with luxury and high street fashion brands. Resident stylist on Channel 5’s award-winning makeover show 10 Years Younger in 10 Days, Gemma is a TV regular and frequently dominates the news headlines.

Gemma’s ability to defy trends and shatter expectations means her extensive roster of clients stay at the forefront of style conversation. Whether a platinum-selling pop star, a talent show judge or award-winning, prime-time TV presenter, Gemma’s fashion-forward styling gets her clients noticed for the right reasons.