Casual outfit ideas for women over 50, selected by a 50+ fashion expert

Look great and feel fabulous in casual outfit ideas for women over 50 selected by an expert stylist

casual outfit ideas for women over 50: cut outs and street style
(Image credit: J.Crew / Getty / Boden)

Whatever your day holds, the best casual outfit ideas for women over 50 will keep you feeling comfortable and looking stylish. Wearable for everything fro meeting up with friends, to running errands, we have all the styling tips you need.

When it comes to casualwear for woman over 50 the options are endless, but it can be challenging to put together an outfit that feels both relaxed and stylish. Many women who spend their working week wearing smart office attire struggle to switch to a more relaxed dress code at the weekend. If you're looking to compile an over 50s capsule wardrobe, include a selection of flattering basics that can be combined with more relaxed piece for casual outfits that make you feel as confident as a tailored suit.

There aren't really any restrictions when it comes to casual outfits for women over 50, and the main thing is that you feel comfortable and confident in your chosen attire. As with any outfit, the first thing to do is to consider the occasion you are attending, as running errands to the supermarket, will differ from picnic outfits, or a lunch with friends. But have no fear, we've found something for every laid-back moment. Of course, the first thing to do is think about seasonality, but whether you're looking for winter or summer outfit ideas for women over 50, there is plenty of choice.

Casual outfit ideas for women over 50

It’s worth spending as much as you can afford on well-fitting basics as these will form the backbone of your casual wardrobe, for example the best straight leg jeans and timeless midi dresses. Megan Watkins, Head Stylist at online fashion destination SilkFred says “I would always recommend a classic wrap dress as they are forgiving whilst being flattering. Some well-fitting linen trousers are also a must in hotter weather for their versatility and ability to keep you cool whilst looking stylish - most tops will pair well with good linen trousers."  

And there are classic casual combinations that work whatever your age "When in doubt, I would recommend opting for a classic white shirt - collars are flattering on both smaller and larger busts - and pairing it with dark wash, boot-cut jeans” says Megan. “This outfit can be worn literally anywhere and layered according to the weather."

Megan isn’t alone in her love for a great pair of jeans, Leanne Lee, Fashion Stylist and Buyer at Blue Bungalow agrees “A well-fitted white shirt paired with dark-wash jeans is a timeless combination. Layer with a long-line cardigan or a duster coat for added sophistication. Complete the look with sleek accessories, such as a structured handbag and classic pumps or comfortable loafers."


If you work in an office setting where the rules are more relaxed on a Friday, or it has a smart/casual dress code it’s important that your choice of outfit combines a more laid-back vibe while still adhering to office rules. Here’s where a pair of the best jeans for women over 50 will work. Avoid skin-tight jeans in faded finishes or ripped styles and instead go for a high-waisted design in a mid or dark denim. Team with a striped top. This could be a classic Breton tee in the summer or a fitted jumper or cardigan in cooler months. Elevate the outfit with a smart leather tote, one of the spring/summer handbag trends 2023, and a pair of dressy flats.


You don’t have to run marathons or endure spin classes to reap the benefits of comfortable gym gear. The combination of a pair of sporty leggings and a loose-fitting sweatshirt is a great option if you have a day of chores to fulfil. The technological benefits of sportwear, innovative fabrics that wick away moisture and keep you cool, will turn your trips to the supermarket into a stylish way to up your daily step-count. And there’s nothing as comfortable as a good pair of trainers, that are equally perfect for walking the dog in the park.


The best midi dresses are a flattering option for a relaxed brunch or lunch with friends, they make a great choice for what to wear on a first date too, making them an extra cost-per-wear buy. “A versatile maxi dress can be dressed up with wedges or dressed down with comfortable sandals.” says Leanne Lee from Blue Bungalow “Add a denim or lightweight jacket for cooler days or evenings. Don't be afraid to experiment with prints, such as floral or geometric patterns, to add visual interest.”


Weekend heroes – these effortless separates are ready to throw on and go. Affordable t-shirts are a great way to add personality to your wardrobe and will give your basics a youthful edge. You are never too old for a band t-shirt. When it comes to directional trousers, a pair of cargo pants are a more trendy choice, but are also a smarter choice than sweatpants, but just as comfy, ideal for sitting on a picnic blanket or laying back with a good book. Style with canvas shoes in a fun finish.


Add a new dimension to your weekend look by switching your jeans for a denim skirt. This A-line midi has a retro '70s feel and will look great with flat mules in the summer and is an ideal way to style cowboy boots in the cooler months. Add an oversized sweatshirt and accessorise with a pretty scarf tied at the neck for a final flourish.


If you like to spend your Sunday wandering around an art gallery or plan to escape to the coast for a walk across the sand, this relaxed and easy-to-wear shirt and trouser co-ord is the perfect outfit choice. Providing just the right mix of smart/casual, the mix-and-match look is versatile too as you can wear both pieces with other basics from your capsule wardrobe. It’s one of the latest trends that suits all women, regardless of age.

How do I look fashionable at 50?

When it comes to dressing to suit your age there are no rules and you should feel free to wear whatever makes you happy. If following the latest trends is important to you then there’s nothing stopping you from wearing the most up-to-the-minute designs. The trick is to research the current trends before you go shopping so you have a more informed outlook. Check out our spring/summer fashion trends 2023 report and our autumn/winter fashion trends 2023 report for the expert’s opinion on the latest styles, colors and runway round-ups. After you have researched the latest trends you can browse the shops and experiment with new styles to keep your look current. If you prefer a classic look that won’t go out-of-date, then a minimalist capsule wardrobe with a solid array of basics that you can integrate with some newer season styles could be the way to go. If that sounds like you, keep to a neutral color palette for maximum versatility and to evoke that Rich Mom aesthetic.

What to wear casually at 50?

Leanne Lee, a Fashion Stylist and Buyer for the women’s boutique Blue Bungalow says:

“Opt for Quality Fabrics: Look for natural fibers like cotton, linen, and silk, as they drape beautifully and offer breathability. Investing in quality fabrics ensures longevity and a more refined appearance.

Play with Color and Prints: Don't shy away from colors and prints. They can inject personality and vibrancy into any outfit. Choose colors that complement your skin tone and experiment with prints in moderation, pairing them with solid neutrals for balance.

Comfort is Key: Casual outfits should be comfortable and allow freedom of movement. Choose fabrics with a bit of stretch, opt for shoes with cushioning and support, and prioritize garments that are easy to care for."

Julie Player

Julie has over 30 years experience in the fashion industry and is a regular contributor to Woman & Home, Woman’s Weekly and Chat magazines, creating engaging fashion and lifestyle content for women of all ages. She also works in the wardrobe department at ITV, dressing the presenters for Good Morning Britain. Aged 57, Julie loves seeking out the most figure-flattering fashion for every occasion. She’s a qualified sustainable fashion expert with a wealth of knowledge of planet-friendly fashion brands and ways to shop more ethically.