6 Winter Style Lessons I Learned From Fashionable Women in Their 40s and Beyond

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 wardrobe 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 winter outfits going forward. 

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. 

Team Who What Wear’s favourite blazer on the high street—or anywhere else for that matter. 

Isabel Marant is known for its classic French style, and this boxy blazer is the perfect nod to Parisian dressing. 

The tie-waist belt makes this jacket look so chic. 

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 cooler, get creative and layer up in black in different textures. 

It’s official: Wide-leg trousers are overtaking jeans in the style stakes. 

I can’t quite believe that you can get a leather dress this good on the high street. Just layer up and belt the waist. 

No wardrobe is complete without a classic wool coat for autumn and winter. 

A black shoulder bag is always a wise investment, but it’s even better if it’s Gucci. 

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: Even in bad weather, bold colours can help bring a little sunshine. Just pair a bright coat with equally fun accessories and a simple shirt. 

This coat already ticks so many boxes, but the flattering double-breasted fit and confident fuchsia makes it that much stronger. 

Everything about this emerald green cardigan is a winner. And trust us—you’re about to see a lot more of long cardigans.

Everyone is talking about Christopher John Rogers and his celebrity clientele, which includes the likes of Zendaya, Lady Gaga and Beyoncé. 

Statement knits don’t get more eye-catching than this. 

Having a trench coat in your arsenal might actually be the smartest purchase you can make this season. As we head out of the transitional period between summer and autumn and firmly into a chilly winter, layering is key, and some of our favourite influencers have already cottoned on to the versatility of the easy trench. Wear oversized and undone for autumn, and opt for a heavier, leather version for winter. Just add a cosy knit. 

Style Notes: Layering a leather trench over a sleeveless knit is perfect for the cooler months when wool coats are too heavy. 

Style Notes: A black trench is versatile enough to wear with anything your wardrobe from knit dresses to wide-leg jeans.

A classic, faux-leather trench that you’ll wear for years to come. 

Fans of cowboy boots will love this Western-inspired coat for its uniquely cool detailing. 

Something about this burgundy colourway makes this leather trench look elegant, expensive and effortless. 

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 a chunky knit and satin skirt, tweed jacket and leather trousers, or a floaty maxi dress with a faux-fur coat and woven accessories, anything that feels good, looks good too.  

Style Notes: Mastering the balance of texture pairing, Emma’s tweed-and-denim combination is polished weekend dressing at its finest. 

Style Notes: Lamé! Pompoms! Satin! This evening look manages to have it all without being overbearing. 

There’s a reason the tweed blazer is a staple in every well-dressed Parisian’s wardrobe. 

I’m not sure what I love most about this dress: the versatility, the cut or the rich, seasonal colour. 

Is it too soon to convince you of the prowess of a cloud soft faux-fur coat? It’ll add a touch of luxury to even the simplest outfit. 

We mean it when we say a Saint Laurent bag is always a smart investment. In fact, we even rounded up 16 of the best.

Our obsession with Loewe accessories continues, and this mohair scarf just went to the top of the list. 

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: A boxy blazer like this doesn’t need over-accessorising. Keep jewellery to a minimum and the shoes and bag 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. 

If you aren’t already familiar with Poetry’s well-crafted, staple pieces, this is the perfect introduction to their classic silhouettes.  

Tuck this jumper into a skirt, or wear it loose and easy with wide-leg trousers. However you wear it, get comfortable in the oversized, relaxed fit. 

An influencer and editor favourite. 

Looking for a wedding guest/party/Christmas/New Year’s dress? Consider this your answer. 

Up Next: We’re in Our 40s and 50s—These Are the Top 5 Trends We’re Wearing This Summer