Comfortable shoes for women over 50 - recommended by a 50+ fashion editor

A 50+ fashion editor recommends the most comfortable shoes for women over 50

comfortable shoes for women over 50: trio of shots - A brown knee high boot, a silver sling back, a bronze heel
(Image credit: Jones the Bootmakers, Vionic, Aldo)

The most comfortable shoes for women over 50 are achievable across all footwear categories. While you may have been willing to suffer for style a decade ago, there is no reason to wear unsupportive, rubbing shoes and the footwear market has really moved on, injecting trending styles with comfort technology. 

While 'comfy' footwear used to be seen as a bit of a euphemism for frumpy, in 2023, that analogy couldn't be further from the truth. As production and shoe technology has developed, so too has the realisation that comfortable shoes can look good too. Look out for specially designed footbeds, padded sides (goodbye bunion pain) and sturdier straps and heels that will ensure you get all the support you need. 

Podiatric surgeon Trevor Prior explains. “The older we get, the more important it is to choose a well-fitting, supportive shoe that is comfortable and holds your foot firmly in place, giving you adequate support. Feet can start to show signs of aging at any age, but it is generally more common from the age of 50 onwards. As we age, feet may get wider and our skin may lose elasticity. Our feet may spread and widen and we often lose padding on the cushioned layer of the balls of our feet, all of which can be painful. Different types of footwear can impact our feet, which may lead to problems in later life.” Trevor continues “Shoes which create pressure on the balls of the foot, such as high heels, can lead to problems as women mature, as they don’t just alter the way your foot functions, they can also affect your body mechanics - how you walk and stand. Pain may be quite mild to start with but, in the long term, the pain may be more chronic.”

How to find the most comfortable shoes for women over 50

Of course, trainers, when it comes to comfortable shoes for women over 50 are the obvious choice, and while this sporty style, particularly the best white trainers are now more common place as a smart-casual shoe option, sometimes a smarter or dressier option is needed.

“Comfort is key but there’s no need to compromise on style,” says personal stylist Jemma Cotterrell. “If you’ve always loved a heel then start thinking about adding a platform sole so you are still retaining the height but looking after the ball of your foot. With flat shoes try to avoid completely flat styles as these make your Achilles tendon work harder and offer no support for your arch. Instead look for a cushioned foot bed, and preferably rubber soles.”


Finding comfortable high heels for women over 50 might feel like a tall order, but this is one area of the footwear market that really has improved in recent years. A heeled evening shoe is key to finish off the best cocktail dresses and other occasionwear attire. Search out shoes that come with additional comfort features like extra padded insoles and arch support to ensure you can stay on your feet for longer. 


To get the most comfortable flat shoes it's all about considered design details. Ideally your flats will have arch support. “Opting for comfort doesn’t mean that 50+ women have to forsake style, as there are several shoe brands which specialise in supportive, fashionable footwear’ says Trevor Prior. “Orthotic shoe brand Vionic has VIO MOTION™ technology built into every shoe, leaving you feeling balanced and supported.” 

Fashion Stylist Jemma Cotterrell agrees that flat doesn’t mean frumpy. “Mary Janes (a flat style with a strap across the vamp) are really having a moment, try to find styles with a small heel and soft leather uppers rather than patent as these will be more comfortable.” As leather has a certain level of natural stretch that will mould to your feet.


When shopping for comfortable knee high boots for women over 50 it’s important to consider the calf width options along with the shape and size of the footbed of the boot. If you are looking for the best wide fit boots, specifically those for wider calves, try brands that offer a selection of width options that will guarantee a comfortable fit. Opt for a soft leather that will provide a degree of stretch and invest in classic shapes that will work well under the best midi dresses or over the best skinny jeans.


When it comes to the most comfortable short boots for women over 50, the main concern is regarding the footbed and the width of the foot of the boot. Styles that come in varied width fittings naturally give you greater control on the final comfort level and is particularly important for those with wide feet. Look for cushioned insoles or side panels to help soften the impact on your feet and sturdy soles. 


“Your shoes should be roomy enough, particularly if you intend to wear them for work every day,” says Trevor. ”Choose quality materials that allow your foot to breathe and which will stretch to accommodate your own foot shape.” is also important as our feet can swell during the day, especially if they overheat..

Personal Stylist Jemma Cotterrall recommends investing in the best loafers for women for a work-wear option. “Chunky track soles offer comfort and height and give us the illusion of slimmer ankles. Slimmer styles with a small heel are great for our natural alignment. The classic penny loafer is sleek, but we are also seeing tassels, studs and embellishment,” for a more directional twist explains Jemma.


When deciding what to wear for a winter wedding it’s important to consider your footwear, especially if you're looking for outfits for mother of the groom or bride. Being on your feet for most of the day and dancing all night requires a high level of comfort combined with a smart aesthetic. If you have additional problems for example a bunion, it is worth spending a bit extra on shoes designed to specifically relieve the associated problems. 

“A bunion is a painful bony bump that develops at the big toe joint, most commonly occurring in adulthood and although (it) can be hereditary,” explains Trevor Prior, “it may also be the result of repetitive trauma, possibly from wearing heels with a narrow toe box. In most cases, bunion pain is relieved by wearing wider shoes with adequate toe room and using other simple treatments to reduce pressure on the big toe".

Specialist brands, including the likes of Sole Bliss - popular with everyone from the Queen Camilla to Helen Mirren, have comfy, style staple shoes for all occasions that are specifically crafted to tackle the bunion issue.

"While I don't have a bunion," explains woman&home fashion editor Rivkie Baum, "I do struggle to find occasionwear shoes that account for my wide feet. I recently purchased a pair of high heeled Mary Janes from Sole Bliss for my a family wedding and was amazed that I could wear them for 12 hours+ straight. The additional side cushioning was a real gamechanger for me".

Our panel of experts:

Trevor Prior
Trevor Prior

A practicing podiatrist in the UK for more than 25 years, Trevor Prior specialises in sports injuries, biomechanics and gait analysis, orthoses, diabetic foot complications and foot surgery - all topics he has lectured on nationally and internationally. Trevor is a Senior Clinical Lecturer in the Sports Medicine department, at Queen Mary University London and is director of Premier Podiatry Limited, a clinic specialising in the assessment and management of foot-related conditions. He has worked extensively with elite and professional athletes in a wide range of disciplines including football, rugby, cricket, hockey and badminton. He is a past Dean of the Faculty of Podiatric Surgery, Royal College of Podiatry, and is a consultant expert in the innovation lab at Vionic Shoes.

Jemma Cotterrell in a blue and white dress in front of a rail
Jemma Cotterrell

A personal stylist and Instagram influencer who has always been obsessed with fashion and clothes and the way they can make you feel. She graduated from the London College of Style with a distinction in personal styling. Prior to this she worked in the designer footwear industry for 20 years, heading up the footwear offer of brands such as Lulu Guinness, Nicole Farhi, LK Bennett and See by Chloe.

Rivkie Baum
Rivkie Baum

With over fifteen years' experience, Rivkie is an accomplished fashion editor, writer and stylist. Covering international fashion weeks, and styling photoshoots all over the world, Rivkie loves translating the trends in an accessible way to make fashion available for all budgets. 

While finding the most comfortable shoes for women over 50 may have felt like an impossible task a decade ago, the movements in technology and the outlook of the industry as a whole has really pushed brands to up their comfort and fit offering. Style and substance should be the norm, not the exception and trying on shoes and being sure of the fit - even if at home is important to ensuring foot health long term as badly fitting shoes will only lead to more aches and pains. Whether you want the best new in boots, smart heels or elegant flats, don't compromise on fit this season.

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.