How To Style: One Dress Four Ways

The key to a successful wardrobe is versatility and with the lines blurred more than ever between work and home life, not to mention the changing nature of social events, our wardrobes need to be flexible. We needn’t think about garments as being for specific occasions so items you can style up and down are your modern wardrobe essentials.      

Helen Canning SS20 style rail close-up

The Shirt Dress

You would be hard pushed to find a brand which doesn’t have some form of shirt dress within its collection so there are always a wealth of options to choose from and it is the most versatile dress which your wardrobe is calling out for. 

This is often the item I select for my clients which initially they may feel unsure about but it’s all in the styling, with a few tweaks a shirt dress can be moulded to fit and flatter different shapes meaning they are universally flattering.

Helen Canning in Reiss SS20 shirt dress

Beginning with a blank canvas: Khaki shirt dress, Reiss 

The Dress: Your blank canvas to style

To maximise styling options I selected a khaki green shirt dress from the new collection by Reiss and I have put together four ways to wear this dress from now, into autumn and beyond…

Helen Canning Reiss dress full-length

Dress, Reiss

Styled for Summer

Let’s begin with how to wear your shirt dress right now in late summer with carefully chosen accessories to complement the khaki green hue and the simplicity of its shape. Layer a multi-chain necklace over, not inside, the neckline for a more contemporary look and opt for a tan leather tote bag that will take you from work to weekend.

 Helen in Reiss dress with accessories

Helen wears: Sunglasses, Warehouse; Necklace, Freedom; Bag, Weekend Max Mara

Style Tip: Neutral animal prints like leopard and snakeskin are a match made in sartorial heaven next to khaki and tan, look for shoes in these textures to finish your outfit.  

Layers for Autumn Days

Helen in Reiss dress layered-up

Helen wears: Top, Reiss; Necklace, Freedom; Belt, Warehouse; Boots, Reiss

When the temperature drops it’s time to bring out the long leather boots which are the ideal accompaniment to The Shirt Dress, worn with long-sleeved tops and fine-knit sweaters layered underneath. With an extra layer you can afford to open the neckline of your dress to show more of your top and introduce a necklace for a subtle glint of gold. 

Style Tip: Use a belt to add definition to your waist and add another element of colour or texture to your outfit, here I used a tan belt but you could experiment with animal prints and bolder colours too - orange looks great next to khaki.

Reiss dress belted

 Dinner Date Ready

Helen in date night look

Leather jacket, Reiss; Belt, Michael Kors; Shoes, Dune

 A leather jacket is your go-to outfit topper; it is a real wardrobe staple to grab and go, finishing outfits from jeans and a tee to floaty dresses so it’s the perfect option for your Date Night look over this dress where a blazer could feel too formal and denim too casual. At the other end of your outfit, barely-there sandals in a shade close to your skin tone will elongate your legs which, with a midi-length dress, is often a welcome styling tweak for a more flattering finish.

Helen dinner date dress look

Style Tip: Reiss and Boss are my top brands in-store for leather jackets from butter-soft classic black bikers to collarless styles in muted tones of navy and maroon.  

Think outside the dress

You have mastered layering tops beneath and jackets atop your shirt dress, now it is time to be a little more creative with your styling. It feels as though much of the year is spent in those transitional seasons where the weather can’t make up its mind and lightweight layers are essential, perhaps this is why the waistcoat has become a hit in designer collections this year. Channel this look and maximise the versatility of your shirt dress by unbuttoning and wearing as a duster jacket-meets-waistcoat hybrid.

 Helen in day-time layering look

Helen wears: Blouse, French Connection; Belt, Oasis; Jeans, Mango

Style Tip: While big sleeves are hot right now, too much volume can swamp your shape so streamline an oversized blouse with a tuck into your jeans and finish with a belt before topping with your waistcoat. 

Helen’s Shirt Dress Edit 

Four other shirt dresses stood out to my stylist’s eye view in-store which show that there really is one for everyone.

Penny Black Striped Shirt Dress 

Penny Black shirt dress

Helen wears: Dress, Penny Black; Belt, Warehouse

Try this open collar dress from Max Mara’s sister brand Penny Black and add glamour with black patent accessories or make it daytime ready by pairing with tan leather.

Lauren, Ralph Lauren Chain Print Shirt Dress 

Lauren summer shirt-dress

Helen wears: Dress, Lauren Ralph Lauren

If shirt dresses are no new thing for you - perhaps you are already a client of mine at Elys - and you have mastered the wear-it-anywhere neutral, try a bright dress. There will, admittedly, be fewer ways to wear it with its bold colour and print but it will look as at home with white trainers and a denim jacket as it will with sandals and a clutch bag.

Lauren shirt dress and sneaker combo

Trainers, Reiss

French Connection Denim Shirt Dress

Do-it-in-denim shirt dress worn by Helen Canning

Helen wears: Dress, French Connection; Belt, Topshop

We all know just how versatile denim is, so a shirt dress in denim is a top choice for your wardrobe. Treat the indigo fabric as a blank canvas to embellish with colour or pattern through your accessories.

Michael Kors Floral Print Shirt Dress

Helen in Michael Kors maxi shirt dress

Helen wears: Dress, Michael Kors; Belt, Oasis; Rings, Topshop

While florals for spring and summer may be anything but ground-breaking, choosing a dark-based floral print opens up the opportunity to wear your dress year-round without feeling like you are in the wrong season. Keep it light in the warmer months with white accessories, pick berry tones and dark neutrals for winter styling and turn to silver and gold for your add-ons after dark.

With endless styling options and a shape to suit everyone, the shirt dress is a wardrobe essential. Need help finding your style? Book a complimentary Personal Styling appointment with Helen and the team.

Remember to share your style with us @elyswimbledon and take a look at Helen’s Instagram for more style inspiration and tips.