How to style dresses for work, day and play

Everything you need to know about how to style dresses

street style models showing followers how to style dresses
(Image credit: Getty)

The question of how to style dresses will always be a popular one, in no small part thanks to their wide-ranging versatility. 

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 midi you might wear to a wedding, the structured denim shirt 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.

Much like your best jeans, Breton top, or beloved camel trench coat, dresses are a staple of almost all closets - whether yours is a streamlined capsule wardrobe or one that’s bursting at the seams.

Mastering how to style dresses for various occasions is an essential skill every woman should master. And even better, it 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 dresses

Sustainability is the word on everyone's lips at the moment, and thinking about how to style dresses before you ‘add to basket’ is a great place to start. Consider 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.

While there are no hard and fast styling rules, the accessories and layering pieces you choose will influence how casual or smart your dress feels, as well as whether it’s seasonally appropriate. To make this part a little easier, we’ve broken our advice on how to style dresses into key trends.

How to style a shirt dress

street style influencers wearing shirt dresses

(Image credit: Getty)

One of the smartest dress styles around, a shirt dress is likely to have a neat collar, button-down front, and structured cuffs. Play into the more formal features by wearing yours with elegant heels and an envelope clutch for a baby shower or fancy brunch, or dress down with chunky trainers, layered necklaces, and a slouchy tote for the weekend. Unsurprisingly, shirt dresses work well for the office, too, especially when buttoned to the top and worn with heeled ankle boots.

Get the look

Me + Em Diamond Geo Maxi Shirt Dress

(Image credit: Me + Em)

Me + Em Diamond Geo Maxi Shirt Dress

Specifications
RRP: $475/£295
Sizes: US: 2-12/UK: 6-16

Baujken Indiana Shirt Dress

(Image credit: Baukjen)

Baujken Indiana Shirt Dress

Specifications
RRP: $181/£129
Sizes: US: 2-14/UK: 6-18

Whistles Eucalyptus Print Dress

(Image credit: Whistles)

Whistles Eucalyptus Print Dress

Specifications
RRP: $259/£129
Sizes: US: 0-14/UK: 4-18

How to style a slip dress

street style influencers wearing slip dresses

(Image credit: Getty)

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. In the summer, styling slip dresses is even more straightforward, just add comfy sliders and a raffia bag. 

Get the look

All Saints Bryony Mutare Dress

(Image credit: All Saints)

All Saints Bryony Mutare Dress

Specifications
RRP: $199/£129
Sizes: UK: 2-14/US: 00-10

Whistles Dagma Twig Print Slip Dress

(Image credit: Whistles)

Whistles Dagma Twig Print Slip Dress

Specifications
RRP: $135/£89
Sizes: UK: 4-16/US: 0-12

Zara Satin Camisole Dress

(Image credit: Zara)

Zara Satin Camisole Dress

Specifications
RRP: $49.90/£29.99
Sizes: XS-XL

How to style a sweater dress

street style influencers wearing sweater dresses

(Image credit: Getty)

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. It also almost goes without saying that this style is best suited to colder weather, when it can be worn for chunky boots or trainers at weekends, and heeled knee-high boots for smarter occasions. Opt for a midi length for a sophisticated feel and accessorize with pieces in the same neutral tone. 

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& Other Stories Belted Wool Knit Polo Midi Dress

(Image credit: & Other Stories)

Specifications
RRP: $119/£85
Sizes: XS-L

Ted Baker Holliis Easy Fit Jacquard Polo Dress

(Image credit: Ted Baker)

Ted Baker Holliis Easy Fit Jacquard Polo Dress

Specifications
RRP: $295/£169
Sizes: US: 2-12/UK: 6-28

Zara Knit Dress With Buttons

(Image credit: Zara)

Zara Knit Dress With Buttons

Specifications
RRP: $49.90/£29.99
Sizes: S-XL

How to style a maxi dress

street style influencers wearing maxi dresses

(Image credit: Getty)

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). This means you’ve got more time to focus on the rest of your look. The addition of a belt or tailored blazer will stop floaty maxi’s from overwhelming your frame, as will styles with a lower neckline. To let a patterned maxi take center stage, keep the rest of your outfit muted, with classic pieces like a straw hat or satchel bag. 

Get the look

Hush Carmine Pintuck Maxi Dress

(Image credit: Hush)

Hush Carmine Pintuck Maxi Dress

Specifications
RRP: $170/£119
Sizes: US: 2-14/UK: 6-18

M&S Per Una Ditsy Floral High Neck Maxi Relaxed Dress

(Image credit: M&S)

M&S Per Una Ditsy Floral High Neck Maxi Relaxed Dress

Specifications
RRP: $69/£39.50
Sizes: US: 2-20/UK: 6-24

Next Tiered Maxi Dress

(Image credit: Next)

Next Tiered Maxi Dress

Specifications
RRP: $55/£36
Sizes: US:2-18/UK: 6-22

How to style a denim dress

street style influencers wearing denim dresses

(Image credit: Getty)

Often similar in shape to the shirt 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. All you really need to do is add a suede ankle boot or box-fresh pair of white plimsolls, but if you did want to liven things up, consider layering a colorful blouse or striped t-shirt underneath. A cross-body bag will add to the utility feel.

Get the look

H&M Oversized Denim Dress

(Image credit: H&M)

H&M Oversized Denim Dress

Specifications
RRP: $39.99/£34.99
Sizes: XXS-XL

Monsoon Dolly Denim Dress in Organic Cotton Blue

(Image credit: Monsoon)

Monsoon Dolly Denim Dress in Organic Cotton Blue

Specifications
RRP: $92/£65
Sizes: US: 4-20/UK: 8-24

M&S Denim Mini Shirt Dress

(Image credit: M&S)

M&S Denim Mini Shirt Dress

Specifications
RRP: $85/£49.50
Sizes: US: 2-20/UK: 6-24