The fashion mistakes that cause real trouble on a date after 50 are practical, and they come from clothes that fit badly, shoes that hurt and outfits chosen without the venue in mind. Shops offer little guidance. The Behaviours Agency reported in 2023 that 69% of British women aged 45 to 60 felt invisible to retail brands, and 62% said advertising rarely showed anyone they could relate to. For women over 50 choosing an outfit for a date, comfort and fit often matter more than following a particular fashion rule.
Shapeless Knitwear and Head-to-Toe Black
Shapeless knitwear and black from collar to ankle are easy to buy and easy to wear, but an outfit without contrast or definition can make the person inside it harder to see. For a woman who already feels ignored by the clothing industry, they are also the path of least effort, especially when 72% of women in that age group say advertising sets unrealistic beauty standards for them. That approach makes sense for a supermarket run and less sense for a dinner with someone she wants to see again. One piece with some shape or colour, such as a fitted jacket or a well-cut dress, is enough to change the effect without making her feel exposed.
Black and loose knitwear are not mistakes in themselves. A well-cut black outfit or a deliberately oversized knit can work just as well when the proportions suit the person wearing them.
Fabrics and Hot Flushes
Some synthetic fabrics, particularly tightly woven polyester and nylon, can trap heat and hold moisture against the skin. For a woman who has hot flushes, a heavy polyester blouse in a warm restaurant can make the evening uncomfortable. Lightweight cotton, linen and breathable moisture-managing fabrics may be more comfortable, depending on their construction and weight.
Layers help for the same reason. A jacket or cardigan over a sleeveless top or a light dress can come off at the table without any fuss and go back on for the walk home.
Size Labels
Women’s clothing sizes are not consistent from shop to shop, and buying by the number on the label is a common route to a poor fit. YouGov asked British women about sizing in 2018, and 54% said sizes varied a great deal between retailers while another 40% said they varied a fair amount. Jeans and trousers were the worst, with 65% and 63% of women reporting large differences, and at some high street chains more than 60% of women said garments came up smaller than the label suggested.
A size number remembered from years ago says little about another shop’s cut today. Trying on, and buying the size that fits rather than the size that matches the old number, avoids the outfit that pulls across the hips or gapes at the waist.
Invitations and Dress Codes
A relationship that starts later in life can quickly include other people’s events. A woman dating an established man may be invited to work dinners, charity functions or family weddings within the first few months, and each of those comes with a dress code, written or assumed. Arriving underdressed at a black-tie dinner, or in a cocktail dress at a garden lunch, is a far more visible mistake than any choice of colour.
“Smart casual” is a common source of confusion. A survey of 2,000 British workers commissioned by the workwear company Simon Jersey found that 34% did not fully understand what smart casual means as a dress code. Asking the host, or the partner who received the invitation, what other guests usually wear takes one message and settles the question before anything is bought.
Bra Fit
A badly fitted bra changes how every top and dress on top of it looks. Most of the 51 women measured in a 2013 Australian study of bra fitting in post-menopausal women were wearing a bra of the wrong size. The researchers noted that breast size tends to change after menopause and can increase even in women who lose weight, so an old fitting is an unreliable guide. A professional fitting before buying a new outfit for a date is a sensible first step, since the bra affects the fit of everything chosen afterwards.
Shapewear for a Long Evening
A dinner date with drinks beforehand can easily last four or five hours, which is a long time to spend in a tight garment. Dr Jamile Wakim-Fleming, a hepatologist at the Cleveland Clinic, has said that very tight body garments worn for long periods can press on the digestive tract enough to trigger acid reflux, and can cause bloating by trapping gas. For women over 50, she also cautioned that tight shapewear may worsen symptoms associated with pelvic organ prolapse.
Her advice on wearing shapewear was to choose the correct size and to limit how long it is worn. A garment one size too small, combined with a three-course dinner and a glass of wine, is the version most likely to make an evening uncomfortable.
Heel Height and Foot Pain
In a 2013 survey for the College of Podiatry, women said their feet began to hurt in high heels after an average of just over an hour. More than 40% of women said they would wear ill-fitting shoes for the sake of fashion, and around 28% had walked home barefoot after a night out.
A dinner date often lasts longer than that hour, and a walk between a restaurant and a bar can add another 20 minutes on foot. A lower block heel or a pair of heels already broken in at home will still look right with a dress, and it lets a woman concentrate on the conversation instead of on her feet.
Coats and Bags
The coat is often the first thing a date sees on arrival and the last thing anyone thinks about when choosing an outfit. A padded jacket bought for the school run or a raincoat worn on the commute for ten winters sends a different message from the dress underneath it, and it stays on through the greeting at the door and the walk to the table. Many restaurants will take a coat at the door, and asking about it when booking means the dress is what the date sees first.
The bag has the same problem. A large work tote full of papers and a water bottle has to go somewhere at a small table, usually on the floor or the spare chair. A smaller bag with room for a phone and keys suits the outfit and stays out of the way.
Ten O’Clock at the Taxi Rank
At ten o’clock, after two hours at the table and a short walk in the cold, the outfit that worked is the one she has not thought about since seven. The jacket is over her arm because the restaurant was warm, the shoes still feel fine, and nothing has needed adjusting all evening. Her date remembers the conversation and, if asked, the colour of the jacket, which is about as much as any outfit should be noticed.
Monica Costa founded London Mums in September 2006 after her son Diego’s birth together with a group of mothers who felt the need of meeting up regularly to share the challenges and joys of motherhood in metropolitan and multicultural London. London Mums is the FREE and independent peer support group for mums and mumpreneurs based in London https://www.londonmumsmagazine.com and you can connect on Twitter @londonmums
