While Gen Z is firmly in the throes of Y2K dressing, those of us who remember the low-slung jeans and crop tops from the first time around are looking elsewhere for some fashionable inspiration. It is a widely known fact that great style is ageless, and some of the most stylish women in fashion are in their 40s, 50s and 60s and have spent a lifetime curating their refined looks while still making current trends work for them.
There are plenty of valuable lessons in figuring out how to build a timeless wardrobe (get ready to take notes) but also how to stay true to your own personal style, as fashion is all about self-expression and what makes you feel good above all else. Having been guilty of buying into a few quick fads and whatever is trending on TikTok, I'm changing to a better approach to shopping, always bearing in mind what will stand the test of time and get the most wear in the future too.
So after looking to some of my favourite over-40 fashion bloggers and influencers for inspiration, I found some reoccurring tips for stylish dressing at any age and for every season. From statement silhouettes to classic must-haves, keep scrolling to see some pointers from the fashion bloggers and influencers who know how to dress in your 40s, 50s and 60s and are inspiring my wardrobe going forward.
1. GOOD TAILORING IS TIMELESS
There is a reason that tailoring is known as "power dressing," and getting the right fit can make you feel incredible. At Who What Wear, we are evangelical about the power of a good blazer, and whether worn as a full suit or paired with skirts and dresses, a well- cut blazer appears in the wardrobes of most fashionable women for its ability to elevate any look. Investing in a good-quality, classic blazer is a shrewd choice. You'll get wear out of it for years to come.
Style Notes: Basing an outfit on one colour palette gives the polished look of a full suit without being matchy-matchy.
Style Notes: Make a blazer evening-ready by swapping trousers for a slip dress and flats for strappy sandals.
Shop the Look:
Team Who What Wear's favourite blazer on the high street is from Arket. That should tell you everything you need to know about it's quality and price point.
Want to nail French style? A boxy blazer is the perfect nod to Parisian dressing.
2. HEAD-TO-TOE BLACK ALWAYS LOOKS EXPENSIVE
According to Neiman Marcus, "Women who wear black lead colourful lives," and there is something to be said about the sense of mystery that an all-black outfit portrays. Elegant, refined and understated, black is a reliable fail-safe for when you want to look put together with minimal effort. Well, if it's good enough for Coco Chanel…
Style Notes: This year, we're trading in the little black dress for a different LBD. The long black dress is a sweeping maxi that scores highly in the style stakes.
Style Notes: As the weather gets warmer, get creative and experiment with layers of black in different textures.
Shop the look:
I can't quite believe that you can get a crochet dress this good on the high street. Just add sandals and a slouchy tote.
No wardrobe is complete without a flat sandal in summer, and these stand out from the crowd.
A crossbody shoulder bag is always a wise investment, but it's even better in black.
3. DOPAMINE DRESSING IS ALWAYS A GOOD IDEA
So now you've mastered head-to-toe black, it doesn't mean that timeless dressing has to be boring. In fact, statement prints and acid brights are the ones we come back to time and again—just ask leopard print and Barbiecore. Celebrate the joy in dressing up by embracing (and even clashing) different colours and prints for a look guaranteed to turn heads for all of the right reasons.
Style Notes: Pink sceptics, take note. Grece shows how to mix and match clashing colours by incorporating her accessories too.
Style Notes: Bold colours can help bring a little sunshine to even the most overcast day. Just pair a bright shirt with clashing trousers and add equally fun accessories.
Shop the Look:
Everyone is talking about Christopher John Rogers and his celebrity clientele, which includes the likes of Zendaya, Lady Gaga and Beyoncé.
This sandal already ticks so many boxes, but the confident red and wearable heel makes it that much stronger.
Everything about this apple green cardigan is a winner. And trust us—you're about to see a lot more of green this season.
4. INVEST IN SMART OUTERWEAR
Having timeless outerwear like denim jackets and trench coats in your arsenal might actually be the smartest purchase you can make this season. As we head out of the transitional period and firmly into summer, coats might not seem like an obvious choice, but as soon as the sun sets, layering is key, and some of our favourite influencers have already cottoned on to the versatility of the easy light jacket. Wear oversized and undone over your favourite summer dress or linen shirt and trousers.
Style Notes: A camel trench is versatile enough to wear with anything your wardrobe from mini dresses to wide-leg trousers.
Style Notes: Take a scroll through Frann's feed and you'll find trenches in just about every colour–a testament to the coats versatility. Anything that gets the French stamp of approval must be chic.
Shop the look:
Fans of Western-inspired styling will love doubling up and wearing this jacket with jeans.
Something about this entirely sheer trench looks elegant, expensive and effortless.
5. PLAY WITH TEXTURE
One of the easiest style dilemmas to solve is how to make a simple outfit feel a bit more special. The answer? Introduce different textures. Pairing the unexpected adds a point of interest—think fine knits and satin skirts, tweed jackets and denim, or a floaty maxi dress with a suede jacket and raffia accessories, anything that feels good, looks good too.
Style Notes: Mastering the balance of texture pairing, Emma's suede-and-cotton combination is polished weekend dressing at its finest.
Style Notes: Linen! Raffia! Leather! This daytime look manages to have it all without feeling fussy.
Shop the look:
There's a reason the linen dress is a staple in every fashion editor's wardrobe.
I guarantee you won't be able to scroll through Instagram without stumbling across this bag or one of it's cute other colourways.
I'm not sure what I love most about this skirt: the versatility, the cut or the graphic take on animal print.
6. BIGGER IS ALWAYS BETTER
Big sleeves, big skirts, big shoulder pads and plenty of attitude… With age comes confidence, best showcased in voluminous dresses, skirts, jackets and knits that bring the drama. And if you aren't feeling your most self-assured, fake it to make it. In a big dress or power shoulder, you can't help but walk a little taller. Fashion forward, and not to mention comfortable, oversized proportions are the secret weapon of some of the most stylish women in fashion, and everyone should have an outfit in their wardrobe that acts as a sartorial pick-me-up.
Style Notes: An oversized bomber like this doesn't need over-accessorising. Keep jewellery to a minimum and the rest of the look simple to let the jacket do all of the talking.
Style Notes: Grece's A-line skirt is proof that you can't go wrong with a big skirt and a refined cashmere knit.
Shop the Look:
This is the perfect way to introduce supersized silhouettes into your wardrobe.
Whether you wear it with fisherman sandals or ballet pumps, get comfortable in this romantic, cotton dress, perfect for a day in the sun.
Looking for a wedding guest/party dress? Consider this your answer.
Remy Farrell is a London-based shopping editor with nearly 10 years of editorial experience covering fashion, beauty and lifestyle. After graduating with a journalism degree and working on the editorial and fashion teams for titles such as Grazia, Elle, Cosmopolitan and British Vogue, she moved into the luxury e-commerce sector, working as fashion assistant at TheOutnet.com styling for the social media channels and helping to develop the collections for the in-house brand Iris & Ink. After expanding an assisting and styling portfolio that includes shooting talent such as Gigi Hadid, Victoria Beckham and Miquita Oliver, she also branched out into beauty, creating tried-and-tested reviews and diverse beauty content.
In her role as shopping editor at Who What Wear, Remy is interested in discovering new and exciting brands to share with the Who What Wear readership and particularly loves uncovering hidden gems at affordable prices to make shopping accessible to everyone.
Born and raised in Sheffield, Yorkshire, Remy moved to London in 2014 and lives in the Docklands with her partner and pug Billie.