6 Style Lessons We 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 to be learned in 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 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. From statement silhouettes to the a classic wardrobe must-have, 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 outfits going forward.

Timeless dressing doesn’t need to be boring, and in fact, some of the most statement prints are the ones we come back to time and time again–just ask leopard print. Celebrate the joy in dressing up by embracing (and even clashing) different prints for a look guaranteed to turn heads for all of the right reasons.

Style Notes: Grece shows to mix and match punchy prints by incorporating her accessories too.

Style Notes: Even in bad weather, colourful prints can help bring a little sunshine. Just pair a block colour coat with a printed dress.

This dress already ticks so many boxes, but the flattering ruching makes it that much more special.

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

It’s a toss up between spots and stripes this season, and this dress makes it even trickier to decide.

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

Having a smart shirt in your arsenal might actually be the smartest purchase you can make this season. As we head into the transitional period between high-summer and the beginning of autumn, layering is key, and some of our favourite influencers have already cottoned on to the versatility of the simple shirt. Wear loose, undone and oversized for laidback appeal.

Style Notes: Layering an open shirt over a dress is perfect for the warmer summer months when a jacket is too heavy.

Style Notes: A white shirt is versatile enough to wear with anything your wardrobe, from linen shorts to leather trousers.

Style Notes: Make pinstripes a little less boardroom with a tank top and sandals.

Lovers of colour, COS’ shirts come in a particularly good palette this season.

A clean, classic that every wardrobe should own.

Check out the clever detail on the back of this shirt, it eliminates all need for stuffing your shirt into your waistband.

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, crochet top and leather trousers, or floaty maxi dress with fringed accessories, anything that feels good, looks good too.

Style Notes: Mastering the balance of texture pairing, Lisa’s leather and knit combination is date-night dressing at it’s finest.

Style Notes: Crochet! Tassels! Raffia! This look manages to have it all without being overbearing.

You may have seen the dress version all over Instagram, but the far more wearable top is a more hidden gem.

Is it too soon to convince you of the prowess of leather? At least try cream, the more summer friendly option.

I’m not sure what I love most about this dress, the cut, the wrap detail, or the rich emerald colour.

Our obsession with raffia bags continues, and this rhinestone one just went to the top of the list.

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 that it’s worn with. 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 around the same colour palette gives the polished look of a full suit without being ‘matchy matchy’.

Style Notes: Make a blazer evening-ready swapping trousers for a slip dress, and flats for a strappy sandal.

Max Mara are known for their timeless camel coats, and this boxy blazer is the perfect seasonal alternative.

Team Who What Wear’s favourite blazer on the high-street. Or, anywhere else for that matter.

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

According to Neinman 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.

We’ve got good reason to believe that jersey maxi dresses are going to be the next big dress trend.

I can’t quite believe that you can get this dress for £50.

It’s official–wide leg trousers are overtaking jeans in the style stakes.

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

Big sleeves, big skirts and plenty of attitude, with age comes confidence, best showcased in voluminous dresses that bring the drama. And, if you aren’t feeling your most self-assured, fake it to make it. In a dress like this, you can’t help but walk a little taller–pretty, practical and not to mention comfortable, these dresses are the secret weapon of some of the most stylish women in fashion, and every woman should have an outfit in their wardrobe that acts as a sartorial “pick-me-up”.