How to Dress in Your Late 40s and 50s: Style Advice from Women Who Get It
Hey there, Wardrobe Warriors! Hil here, co-owner of Wardrobe at The Cross, and today I’m tackling the billion-pound question: how on earth do we dress when we’re in our late 40s and 50s? I’m 48 myself, and Sue—one of my best friends and co-owner of our gorgeous shop who originally met my husband at university way back in the 80s—is 59. So, believe me when I say, we understand what it’s like to navigate the ups and downs of dressing at this stage of life.
We’ve both been on the same journey as you: the menopause rollercoaster, changing body shapes, and fluctuating confidence. Sometimes I wake up and look at myself in the mirror and think, ‘hold on, is that actually me?’ I don’t look how I expect to look (identical twin of Jennifer Anniston, obvs) because I feel about 22, not 48. Although, full disclosure, some days my knees creak like a 90 year old’s.
But here’s the good news: you don’t need to change your body—you just need to change how you dress it! It’s all about feeling confident in yourself, and ready to tackle whatever comes your way from heading into work to going to the pub quiz. PSSST the pub quiz is Sue’s fave Thursday night distraction, but don’t say I told you. She cleans up every time… that woman has a brain like a razor…
At Wardrobe at The Cross we have amazing customers of all shapes and sizes – take a look at our google reviews, those customers have a lot to say about how fab our shop is – and our exquisite, hand picked clothes from sizes UK 8 to 20.
So, let’s dive in, and I’ll share my fashion tips for over 40s and 50s, with a dash of ‘Hil’ humour, some personal insights, and hopefully, a few lightbulb moments.
Fashion Principles for Women in Their 50s
As we enter our late 40s and 50s, the principles of dressing start to shift. It’s not about blindly following trends – because if you did that you would be wearing ridiculously oversized blazers and cycling shorts – but focusing on what makes you feel fantastic and comfortable. Here are some key styling principles we keep in mind when styling customers in store or virtually.
- Prioritise Fit Over Size
Forget the number on the label. I’ll say it again for those at the back. IGNORE the size in the label. It means nothing. I have pieces in my wardrobe that range from a size 8 to a size 16 and they all fit me. Right now. The UK high street appears to know nothing – I’m looking at you Zara, H&M, M&S – about the consistency of sizing.
I am a size 10 or 12 in most shops, but that doesn’t mean that I care what is on the label. In fact, most Scandinavian brands (our shop is chock full of ‘em) work in numbers that start at a 34 and go up to 42. 34 is a size 8, and I usually fit into a 36 or 38. But sometimes I am in the 40, and I do not care a jot. Because I want the piece to fit and flatter. Here is an example to show you what I mean:
These are the best low-key, i’m-having-a-casual-day-but-I-want-to-look-stylish trousers I have ever worn. I have them in the navy (Total Eclipse) and the black and I take a size L/40 in both. Not a Medium, and not a chance am I getting into the Small. Why? Because these amazing trousers come up neat and I want to be able to eat a large sandwich and a chocolate bar at lunchtime. Size L? L is for LIFE, I tell ya!
In your 50s, your shape will change, and that’s perfectly normal. I got to 44, started an appalling peri-menopause and noticed that any semblance of a waist I did have had ‘left the building’. The building in this instance being my care-worn, twice-pregnancied, cellulite ravaged body.
But, if you invest in pieces that accentuate your best features and perhaps skim over the areas you feel less confident about (yes tummy, that’s you!) then you have a great starting point.
- Quality Over Quantity
In your 50s, your wardrobe should be more about having fewer, high-quality pieces that you can mix and match. This is also far better for Mother Earth too. She has a stake in the game called ‘fashion’ for obvious reasons. Invest in well-made, classic items like a divine denim jacket made from soft-as-a-kitten fabric or a perfect pair of jeans. They’ll elevate your style without chasing trends. This denim jacket (see below) is one of our perennial favourites. It can be worn over so many outfits, winter and summer and the fabrication is second to none.
In fact, as you’ll see in this blog, the brand My Essential Wardrobe is exceptionally well suited to us women ‘of a certain age’ because the fits and fabrics are to die for. No skimpy finishes here, NO SIR! And all the sweat pants (see above images) and tees have moisture wicking properties due to their bamboo fabrication. Joyous for times of hot flushes……. The joggers and tees are super soft to the touch too. I’ve two customers who come in simply to stroke them! Each to their own, ladies, each to their own. This is a judgement free zone x
- Embrace Colour and Texture
As we age, our skin tone can change, so experimenting with different colours can do wonders. Jewel tones, soft pastels, or rich earth tones can brighten your complexion and give you that natural glow. Sue is a fully trained colour analyst – the London College of Style is THE place to study for this qualification and she got top marks – and she has helped me so much with understanding colour and how it can be transformative when thinking about dressing in your 40s and 50s. For example, initially I was sceptical about this stunningly bright chartreuse blouse below but she showed me how it illuminates my face and eyes. I wear it very regularly now both with jeans and black trousers.
For a better understanding of how colour analysis and personal styling can be totally and utterly change-making then read more about Sue’s services.
Wardrobe Essentials for Your 50s
Building a solid foundation is key to dressing confidently in your 50s. Here are a few wardrobe essentials every woman should have:
- A Great Pair of Jeans
Finding the perfect pair of jeans is a must. My personal favourite? TOXIK jeans. They’re high-waisted with plenty of Lycra for stretch, and they hug in all the right places. I’ve even been known to do lunges around the store to show how stretchy they are! Whether you prefer skinny (still fashionable despite what the powers-that-be at Vogue might have you think!) or wide-leg, these jeans will be your go-to. I have them in every wash and every fit – Sue gets sick of the sight of my newly pert behind in these bad boys!
Fear not if you think these look a little bit ‘ankle swingy’ on the amazonian model above – rest assured if you’re like me, at five three and three quarters (!) they are the PERFECT length with a chunky trainer and I LIVE and DIE in them. In fact, you heard it here first, BURY me in them. Just not yet. I have a shop to run……
Don’t forget to add the perfect belt, though. And boy do we have one; waist-cinching and very designer-inspired if you (nudge, nudge..) catch my drift.
- The Perfect Blazer
A structured blazer is a fantastic addition to a peri/postmenopausal wardrobe because it provides shape and definition, particularly around the shoulders and waist. As hormonal changes can sometimes lead to a loss of waistline or softer tummies and arms, a well-tailored blazer helps create a balanced, flattering silhouette.
The sharp lines give structure without feeling too rigid, allowing you to feel polished (who doesn’t want feel polished, I ask you?) and confident. A blazer can easily dress up an outfit, making it both versatile and timeless. Pair it with jeans or tailored trousers for effortless chic that celebrates your shape in all the right places.
The quintessentially perfect blazer is, yet again from My Essential Wardrobe and it fits like a glove. I wear the 38 in this perfectly proportioned piece and manage to look at least a stone lighter, even when I am hormonally bloated. You can thank me later wardrobe warriors….
- Versatile Dresses
Look for dresses that have a bit of structure, like our Onjenu range. These dresses and jumpsuits feature double-layered-power-mesh waistbands that create a waist even if you don’t naturally have one (that would be me…) and they’re flattering on all shapes. They’re perfect for day-to-night wear and make you feel fabulous every time you slip into their silkily soft jersey folds. Some of our customers think there is actual magic and wizardry involved so good is the fit.
Onjenu is a truly brilliant brand, designed by women, for women, with a deep understanding of how clothes should make you feel. Created by a London-based designer who, after having her baby, struggled to find dresses that suited her changing shape, the brand is all about empowering women of all shapes and sizes.
The luxurious Italian fabrics feel as good as they look, and the jersey dresses are simply stunning—effortlessly draping over the body to create a supremely flattering silhouette. I wear a size 12, Sue a size 8, and we both love how these pieces work beautifully for every occasion keeping you warmer in winter with tights or cool in summer with sandals or wedges.
Whether it’s a busy workday, a special event, or just an easy-going day with trainers, these dresses and jumpsuits tick every box. They celebrate inclusivity, style, and comfort, answering the real needs of real women.
- The Standout Piece
Having a standout piece in your wardrobe becomes even more important when you’re post-50. It’s not just about looking good; it’s about feeling fantastic and confident in what you wear. By this stage in life, you know who you are and what you love (and if you don’t then do come in and try our in person styling, or contact us for one-to-one virtual styling…) , so having that one piece that really speaks to you can make all the difference.
A beautifully made, standout item—whether it’s a stunning skirt, a unique dress, or a show-stopping accessory—gives you a sense of pride every time you put it on.
It becomes a conversation starter, something that draws people in and gets them talking. After all, why blend into the background when you can shine? You deserve to wear something that expresses your individuality and style, a piece that reflects the vibrant, interesting person you are.
Personally I am loving this sequinned skirt from Soaked in Luxury, right now. In fact the eponymous brand is also known for offering solution dressing for women over 50 who may struggle with body confidence issues. It offers flattering, effortlessly chic designs that enhance confidence. Their sumptuous Scandinavian collections focus on stylish, well-tailored pieces that celebrate every body type, embracing curves without compromising comfort. With soft fabrics and versatile silhouettes, Soaked in Luxury’s pieces are timeless, making our customers feel beautiful and empowered. This brand understands that fashion is about feeling good in your skin, and their clothing helps mature women express their personal style while providing a boost of self-assurance in every outfit. Genius, non?
- Layering Pieces
Layering is key, especially when it comes to elongation of silhouette and also arm coverage. Yup, the dreaded and much feared ‘Bingo Wings’. We know many of you prefer to cover the tops of your arms as skin elasticity changes. At Wardrobe at The Cross, we stock a wealth of of lightweight knitwear, tops, and blouses with three-quarter sleeves or longer to give you comfortable and stylish coverage.
The Casey Puff Cardigan is one of our O.G bestsellers for a reason. It’s an absolute winner for mature women who simply need the ‘piece de resistance’ layering piece. Feeling hot one minute and freezing the next? This lightweight layer is your new best friend – throw it on when the chills hit and shrug it off when the heatwave (aka menopause ‘glow’) strikes. Plus, those fabulous puff sleeves give you a bit of drama while keeping the tops of your arms stylishly undercover. It’s perfect for when you want to look effortlessly chic but also be ready for whatever your hormones throw at you. Style and comfort – sorted.
Dressing for Your Body Shape & Lifestyle in Your 50s
Understanding your body shape and dressing accordingly is crucial in your 50s. Whether you’re curvier, petite, or somewhere in between, there are ways to dress that will enhance your figure and suit your lifestyle. Sue and I are experts in this and we love nothing more than helping our customers find the perfect piece for an upcoming occasion or the perfect fit for date night.
🍎 For Apple Shapes:
If you carry weight around your tummy, opt for high-waisted trousers like the My Essential Wardrobe Black Knit Pants and to create definition at the waist. As someone with bigger boobs and a short waist, I find V-necks to be my best friend for elongating the torso. I wear the Black Colour V Necked Faye Top all the time because the neckline is super-flattering and the gentle ruching hides a multitude of sins!
And don’t underestimate the power of a good French tuck. It’s basically the lazy girl’s answer to looking fab without trying too hard! You just tuck the front of your top or blouse in and let the rest hang loose—easy peasy. For women over 50, it’s an absolute game-changer because it gives you a waistline without screaming, “Look at me, I’m tucked in!”
Plus, it sneaks in some leg-lengthening magic while giving you a bit of belly camouflage. So, you can feel put-together and still rock that comfy, cool vibe. It’s the cheat code to looking effortlessly stylish—who doesn’t love that?.
Sue and I like to think we introduced the French tuck to Neston—our humble gift to the world!
🍐 For Pear Shapes:
Balance out fuller hips by drawing attention to your top half. Tops with detailing around the shoulders and boobs like boat necks or ruffled collars work beautifully. I recently styled one of our newest customers in this stunning Saint Tropez Lilja Ruffled Blouse and was amazed at the balance it lent to her silhouette. I love it when that happens. She practically did a whoop of joy right there in the fitting room.
⌛ For Hourglass Figures:
Hourglass figures like Sue’s benefit from styles that emphasise the waist. Here again, Onjenu Dresses & Jumpsuits come into their own. These pieces are a dream for hourglass figures because they know how to work with your curves, not against them! With their cinched waists and drapey, flowing fabrics, they hug all the right places while skimming over the bits you want to keep under wraps.
The brand loves a good wrap or belted style, which perfectly highlights an hourglass figure’s natural waistline. Plus, the bold prints and stretchy fabrics mean you’ll be comfortable while looking like a total knockout. Basically, Onjenu pieces are like a love letter to your curves—flattering, forgiving, and fabulous.
Navigating Fashion Trends in Your 50s Without Losing Your Personal Style
While trends can be tempting – believe me, I have tried ski pants and it wasn’t big and it certainly wasn’t clever – but it’s all about choosing the right trends and incorporating them in a way that aligns with your personal style. In your late 40s and 50s, you want to stay current, but not feel like you’re trying too hard. Here’s how:
- Adapt Trends to Suit You
If cropped trousers or wide-leg jeans are in, consider how they work with your body shape. Rather than jumping headfirst into every trend, take inspiration and tailor it to your wardrobe. For instance, if you love brights and they truly lift your spirits, but you don’t want to feel overwhelmed, try incorporating a bright scarf or accessory. It’s a gentle, experimental nod to something with which you might go further and it’s a way of testing the waters.
- Stick to Timeless Pieces
Classic cuts and styles will always serve you well. Things like a well-fitted dress – dare I mention Onjenu again? – or a great pair of black trousers are your wardrobe warriors. They go to battle on your behalf. By all means, experiment with trends, but keep your wardrobe rooted in timeless, fabulous pieces.
Fashion Faux Pas to Avoid in Your 50s
While there aren’t strict “rules,” there are some common fashion missteps we tend to see in women’s wardrobes as they get older. Here are a few things to avoid:
- Oversized or Baggy Clothing
While comfort is key, clothes that are too baggy can actually make you look bigger than you are. Instead, opt for tailored pieces that fit your shape without clinging. I recently styled an amazing customer who is a gorgeously proportioned UK size 16 but she was covering her fabulous figure in oversized sweats and leggings. Not purchased from Wardrobe at The Cross, I hasten to add.
During our session, we built her a capsule collection of 6 pieces that, when pulled together or worn with existing pieces from her wardrobe, really gave her back a sense of how extremely amazing she looked.
- Over-Accessorising
We love a good statement necklace or bold earring like the Emerson Drop Earrings, but it’s important not to overdo it. Less is often more, and the right accessory can elevate a look without feeling too heavy.
Coco Chanel famously said, “Before you leave the house, look in the mirror and take one thing off.” This advice is all about avoiding over-accessorising and keeping your look chic and elegant. Chanel believed in simplicity and balance, reminding us that less is often more when it comes to fashion. I’ll be honest with you, Sue does have to remind me of this famous aphorism because I can go OTT (over the top) with the jewellery if I’m not careful.
- Outdated or Ill-Fitting Bras
This one’s key—if you haven’t updated your bra drawer in years, now’s the time. The right bra can make a massive difference to how your clothes fit. In fact, it’s the foundation of your entire wardrobe! We don’t stock bras in our boutique but we know exactly where to get the very best underpinnings and we do hold a good selection of sucky-in-knicker-shorts and slips from Coster Copenhagen.
How to Find Your Signature Style in Your 50s
In your 50s, it’s the perfect time to hone your signature style—the look that makes you feel the most “you.” Here are some tips for finding your personal style:
- Take Stock of What You Love To Wear
Go through your wardrobe and figure out which pieces make you feel amazing. Whether it’s a certain cut of dress, a fabric, or a colour that makes you glow, build your wardrobe around those pieces.
- Don’t Be Afraid to Try Something New
Even though you’re focusing on signature style, it doesn’t mean you can’t experiment! Try on things you wouldn’t usually gravitate towards—you might be surprised at what works for you.
- Trust Your Instincts
At the end of the day, you know your body and your style best. If something doesn’t feel right, don’t wear it. The key to looking great is feeling confident in what you have on.
Dressing in Your 50s is About Empowerment, Not Rules
Ultimately, dressing in your 50s is about feeling empowered. Sue and I have worked with women of all shapes, sizes, and ages, and one thing we’ve learned is that fashion should make you feel good—not restricted by arbitrary rules.
We’re here to help you embrace your body as it is now, with clothing that fits beautifully and helps you feel fabulous, no matter what life throws at you.
I hope you’ve found these tips helpful and maybe even had a giggle or two. I know that I did writing this blog. In fact, I nearly wet myself at one point when I got up too fast mid snort of laughter. Just another perimenopausal peril, ladies! #tenaisyourfriend
Dressing in your 40s and 50s doesn’t have to be a headache, and it’s certainly not about hiding away. Whether you’re an apple, a pear, or an hourglass, you can dress in a way that makes you feel confident, stylish, and totally you.
Pop into Wardrobe at The Cross, or book a personal styling session with Sue or me. Let’s get you feeling your best, and don’t forget—style has no age limit, and neither does a good pair of jeans!
