Dresses for older women that are as flattering as they are fun

(Image credit: Sofie Delauw/GettyImages)

This summer might not be the one you had planned, but that doesn’t mean you can’t still dress the part.

First things first, remember there’s no upper-age limit when it comes to fashion. Dressing in your sixties isn’t about dutifully following trends, but finding your very own signature style.

And of course, you can’t go wrong with a dress.

MORE:The best dresses with sleeves

Whether you’re wearing yours to work, dinner with friends or even for a socially distanced stroll, this wardrobe staple will never let you down.

We’ve done the scrolling for you and picked out the very dresses for older women the high street has to offer – happy shopping!

Dresses for older women

Linen Checked Midi Fit & Flare Dress, £39.50

You could say the 60s shift is making a comeback, but in our opinion – it never left. The straight shape makes it one of the perfect dresses for older women, gracefully skimming your frame. This M&S beauty is ever so slightly nipped in at the waist, drawing the eye to the smallest part of your middle. Even better, it’s crafted with M&S’ patented Comfort Cool Technology to keep you comfortable whatever the weather.

SHOP NOW: Linen Checked Midi Fit & Flare Dress, £39.50, M&S

Pleated Chiffon Dress, £34.99

Light, floaty and delightfully swishy, this midi has it all. The neat round neck and pin-tucked front are really elegant, while the satin lining makes it a joy to wear. The deep turquoise shade is easy to dress up or down, depending on what you’re up to. Wear during the day with flip-flops and a straw tote, swapping for heeled wedge sandals and an embellished clutch come evening.

SHOP NOW: Pleated Chiffon Dress, £34.99, H&M

Loved&Found Numph Nubeige Dress, £99

The classic shirt dress has been given a personality-packed overhaul in this pink printed frock. A busy pattern will not only hide a multitude of sins, but takes the pressure off accessorising – just add simple neutrals like a pair of white canvas trainers and you’re good to go. The tiered ruffle and pretty-puff sleeves add extra interest, while the tapered cuffs and high neck stop the wide shape from overwhelming your frame.

SHOP NOW: Loved&Found Numph Nubeige Dress, £99, John Lewis

Belt Shirt Dress, £59.99

Effortlessly chic, a gorgeous shirt dress will work hard in your wardrobe. Wear this peachy-pink number buttoned up with sandals, or open kaftan-style over a pair of white linen trousers and a vest. It could even work as a beach cover-up if you’re lucky enough to be getting away this summer. The adjustable belt is also detachable, so you can swap it for a more statement piece if you prefer.

SHOP NOW: Belt Shirt Dress, £59.99, Mango

Ditsy Floral Embroidered Dress, £70

Monsoon know a thing or two about what makes a great dress, and this doesn’t disappoint. A deep V-neckline will make the most of a larger bust, or create the illusion of curves on petite frames. By bringing the eye downwards, it works to create a more streamlined silhouette. If the ditsy floral print wasn’t enough to win you over, the romantic embroidery will.

SHOP NOW: Ditsy Floral Embroidered Dress, £70, Monsoon

Blue Angel Sleeve Midi Shirt Dress, £35

The dress equivalent of your trusty jeans, a denim dress is a failsafe option. The neutral colour means it’ll slot easily into your existing wardrobe, while the pale blue-hue is universally flattering. This is made from a lightweight denim for extra comfort, and could easily be layered up with knitwear when the weather turns. The wide cap sleeves are great if you’re conscious about showing off the tops of your arms, simply floating over them.

SHOP NOW: Blue Angel Sleeve Midi Shirt Dress, £35, Dorothy Perkins

So which option will you choose?

Jess Beech

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.