By Jess Beech
The question of how to style a shirt dress or a slip dress–heck, any type of dress, will always be popular. There are no two ways about it, dresses are a failsafe wardrobe staple—whether you're heading back to school or hitting the city streets.
It’s a question that will always demand a broad answer, too, simply as there are so many different styles of dresses to choose from. There’s the romantic slip dress you might wear to a wedding, the structured denim dress that’s smart enough for both work and play, and the laid-back jumper dress for cozy, laid-back weekends - to name just a few. And each of those could just as easily work for a different occasion. The best dresses are as versatile as your best jeans, with the potential to be worn in a myriad of different ways.
This season, timeless pieces like the shirt dress and maxi dress remain popular, with square necklines, puff sleeves, and breezy trapeze shapes among the key clothing trends.
Typically, trends and sustainable fashion, the phrase on everyone's lips at the moment, don’t tend to mix. But investing in new pieces needn’t be a problem, as long as you’ve considered how to style your new purchase before you ‘add to basket’. Think about where you’d wear your potential purchase and how many existing pieces in your wardrobe it would go with. If you’re unlikely to wear it more than seven times, or don’t know what you’d wear it with, then it’s likely not worth investing in.
Would your new dress work as well in winter as it would in summer too? While there are no hard and fast styling rules, the accessories and layering pieces you choose will influence how seasonally appropriate your dress is, as well as how casual or smart it feels. To style your dress for winter, temper bright colors, floaty shapes, and barely-there cuts with the addition of base layers and knitwear in darker, moodier hues.
Mastering how to style dresses for various occasions and seasons will help max out the cost-per-wear of your new buy and feel confident every time you wear it. You can thank us later.
How to style a shirt dress
Not sure how to style a shirt dress? We've got you covered. One of the smartest dress styles around, a shirt dress is likely to have a neat collar, button-down front, and structured cuffs. For this reason, they work well for day, play and the office.
How to style a shirt dress for day
Added extras like chunky trainers, layered necklaces and a slouchy tote will all make your shirt dress feel more weekend appropriate. “Shirt dresses always work well on holiday too,” explains Deputy Fashion Editor Charlie Bell. “Wear unbuttoned over a swimsuit and you’ve got yourself a fancy beach cover-up.”
Personalised Layered Birthstone Necklace Set: £30 | Not On The High Street
With a layered necklace you can dress up a shirt dress for the weekend without making it look too formal. This personalised layered necklace will help you make a statement about yourself with the pretty dainty birthstone and customised initial pendant. You can also between silver and gold options to match your signature look.
How to style a shirt dress for evening
Play into the more formal features of your shirt dress by teaming with elegant accessories. "Button to the top and add chic court shoes for a more formal look," advises w&h's Style Editor Joely Chilcott. “Or, loosen the top buttons, add a lace camisole underneath and a statement earring for a more laid-back, yet still dressy feel.” Easy!
How to style a shirt dress in winter
"I love wearing dresses all year round and a shirt dress is so adaptable,” says Charlie Bell. “In winter, I layer shirt dresses over fine roll necks for extra warmth and pair with stompy boots.” Follow Charlie’s lead by wearing your shirt dress with a timeless pair of Dr Marten’s. An easy way to make your dresses country-walk appropriate.
Fashion Editor's picks–shirt dresses
Whistles Rowan Irregular Spot Dress
Me + Em Diamond Geo Maxi Shirt Dress
Whistles Eucalyptus Print Dress
How to style a slip dress
Silky, slinky and more than a little bit sexy, the slip dress has been enjoying a revival in recent seasons. Block colour or printed, the choice is yours.
How to style a slip dress for day
How to style dresses that are typically ‘evening only’ for daytime is far easier than you might think. The key is in layering and fabrics. So, instead of teaming with something luxe like a fur coat or velvet jacket, layer under or over chunky knits, crisp white shirts, and linen blazers and finish off with a stylish pair of white trainers. In the summer, styling slip dresses is even more straightforward, just add comfy sliders and a raffia bag.
Vegan Lighter Lace Up White Chunky Sneakers: $105 (£79) | Kurt Geiger
Make a real style statement by pairing your slip dress with these trendy white sneakers that feature a modern rosy croc finish on the heel for a dressy but daytime feel. We also love the touches of light pink on the tongue that makes these stand out a bit more—pair them with a pastel-colored slip dress for a dainty but edgy daytime look.
How to style a slip dress for evening
“A slinky slip dress can feel daunting at first but they are actually super easy to wear,” explains Charlie Bell. “Understated and elegant, the shoulder-baring style is a go-to for long summer evenings. Just team with barely-there sandals and delicate jewellery for a 90s Jennifer Aniston inspired look.” If you’re cautious about showing off your arms, a structured blazer draped over your shoulders is an easy solution. Plus, it’ll keep you warm past 10pm too.
How to style a slip dress in winter
Layers, layers and more layers! The barely-there cut of a slip dress means they’re not the obvious choice for colder months, but that doesn’t mean you need to pack yours away until spring. By wearing a cropped jumper over the top, you can create the illusion of a separate skirt. Or, if you have a fine knit or white shirt in your wardrobe, layer your slip dress over the top. Double-down with your best winter coat and a pair of cosy boots too.
Fashion Editor's picks–slip dresses
All Saints Bryony Mutare Dress
Ted Baker Fileyy Print Midi Dress
Zara Satin Camisole Dress
How to style a sweater dress
Cozy? Yes. Chic? Also yes. It’s this winning combination that gives the sweater dress the potential to become one of the hardest working pieces in your wardrobe.
How to style a sweater dress for day
“Layering is your best friend,” explains stylist and editor Hannah Eichler. “You can easily switch up the look with clever (but very simple) styling tricks - a utility jacket over the top, layer a shirt underneath so you can see the collar and cuffs or pop a polo neck under.” As for shoes, the world is your oyster. Add interest to otherwise simple knits in neutral tones with colourful, “Dad” style trainers. Chunky boots, and bags heavy on hardware (think contrasting zips, chains and buckles), will give feminine silhouettes an edge.
Hat Box Deep Shine Tea Rose Small Croc: $700 (£495) | Aspinal of London
Aspinal of London is already a favorite of the Royal Family, with Kate Middleton, Meghan Markle, the Duchess of Cornwall and even the Queen famously fans of the London-based brand—so of course it's one of our go-tos for the best designer bags around too. While they have so many stylish designer bags to choose from, we love this dainty pink offering that oozes feminine sophistication with its rosy hue but adds a hint of edginess with the croc leather. The inner compartments are also really handy for getting your bits and pieces organized.
How to style a sweater dress for evening
Think the sweater dress was only to be worn pre 7pm? Think again. Opt for a figure-skimming style in an elegant midi length for a chic evening outfit you’ll comfortably be able to eat 3 courses in. “I’d wear mine with simple jewelry and a neutral mule for a timeless look,” says Amber Jackson, Fashion Editor at ITV’s This Morning. If you’re conscious about your middle, follow Hannah’s lead and stock up on the best shapewear. “When I’m wearing jumper dresses I always pick supportive undies to make sure I feel secure. Fantastie Smoothease Invisible Stretch Briefs are hands down the comfiest I have ever worn.
How to wear a sweater dress in winter
It also almost goes without saying that the sweater dress is best suited to colder weather. So, if yours is made from wool and boasts a nice chunky knit, it shouldn’t require much in the way of extra layers to keep you snug. For days when the mercury is seriously low, add a tailored wool coat, a roll neck and 200 denier tights. Otherwise, a pair of knee-high boots and some simple gold jewellery is all you need.
Fashion Editor's picks–sweater dresses
H&M Knit Dress
& Other Stories Belted Wool Knit Polo Midi Dress
Ted Baker Holliis Easy Fit Jacquard Polo Dress
How to style a maxi dress
Easy to spot thanks to their floor-sweeping length, maxi dresses are our go-to for fuss-free dressing. If you're petite, you may need to budget for alterations, while those 5'9" or taller may find most maxis skim your ankles.
How to style a maxi dress for day
One of the best things about styling a maxi dress is that the floor-skimming length means there’s no need to worry too much about your shoes (or fake tanning your legs, for that matter). Make the most of this easy-breezy dress style by slipping on a pair of flip-flops and throwing a raffia tote over your shoulder. Summer dressing at its simplest.
How to style a maxi dress for evening
Although most often associated with long summer afternoons, the extra length means maxi’s can easily make the transition into evening wear. The addition of a belt or tailored blazer will stop floaty fits from overwhelming your frame, as will styles with a lower neckline. If your maxi boasts a busy print, keep your accessories muted in neutral shades of black, white or tan.
How to wear a maxi dress in winter
“Don't assume maxi dresses are just for breezy summer dressing, make them work for winter too,” says Joely Chilcott. “Add a thin knit roll neck underneath to introduce an extra warm layer without adding bulk and pair with chunky boots.” Adding different textures like leather and faux fur into the mix will help to lessen the summery feel of your holiday favourites.
Fashion Editor's picks–maxi dresses
Kitri Amaya Blue Floral Dress
H&M Sleeveless Maxi Dress
Next Tiered Maxi Dress
How to style a denim dress
Denim dresses have the added bonus of not feeling too far removed from your trusty jeans. And just like jeans, the darker the shade of denim you choose, the smarter and more flattering they will look. Similar in shape, much of the advice is similar to how to style a shirt dress.
How to style a denim dress for day
Effortlessly chic, the denim dress doesn’t need much styling for everyday wear. A suede ankle boot or cross-body satchel in khaki or tan will play up the utility feel of a buttoned-up design. If you did want to liven things up, consider layering a colourful blouse or striped t-shirt underneath your denim dress. Anything that you’d normally wear with your jeans, goes.
How to style a denim dress for evening
“The trick to giving daytime classics a glam spin is to play with texture and shape,” says Hannah Eichler. “A smock shape can easily be cinched in with a metallic belt to add a more fitted silhouette, a pair of fun colourful raffia wedges will give a playful feel when you’re letting your hair down with a cocktail, and there’s always a fail safe flash of red lippy which is denim’s perfect party partner. A makeup artist recently told me to mix Mac Ruby Woo and Lady Danger and I love the combo.” Forecast not playing ball? “I’d style a denim dress for an evening out in autumn or winter with a knee high, heeled boots if it was short or white ankle boots if it was midi,” says Amber Jackson.
How to wear a denim dress in winter
Thanks to the sturdiness of the fabric, denim dresses are perfectly suited to colder weather. Indigo and black washes already have the season’s typically muted colour palette covered, while lighter and acid wash denim can be made winter-appropriate with the addition of a black roll-neck or tights. Use playful outerwear to put your own spin on this wardrobe staple. Think an oversized faux fur coat, colourful beret or patterned blanket scarf.
Fashion Editor's picks–denim dresses
M&S Per Una Denim Belted Midaxi Tiered Shirt Dress
Monsoon Dolly Denim Dress in Organic Cotton Blue
Fatface Harper Denim Dress
Jess Beech is an experienced fashion and beauty editor, with more than eight years experience in the publishing industry. She has written for woman&home, GoodtoKnow, Now, Woman, Woman’s Weekly, Woman’s Own and Chat, and is currently Deputy Fashion & Beauty Editor at Future PLC.
She caught the magazine bug during a stint as Fashion Editor of her university newspaper alongside her English degree, and hasn’t looked back since. As for the fashion bug, that came as part and parcel of growing up in the 90s, but the less said about that the better!
Jess’ average day in the office is spent researching the latest fashion trends, chatting to industry tastemakers and scouring the internet to bring you this season’s must-buy pieces - as well as advice on how to wear them. Weekends are equally fashion-focused, and Jess has been known to visit no less than five Zara stores in a single day in search of the perfect occasion dress.
The only thing that comes close to a buzz of finally tracking down that much-coveted dress is the joy of discovering a new beauty wonder product or hero ingredient. A beauty obsessive, Jess has tried everything from cryotherapy to chemical peels (minus the Samantha in Sex and The City-worthy redness) and interviewed experts including Jo Malone and Trinny Woodall.
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