A man who starts dating again at 55 usually does so with a wardrobe that was bought for other purposes. The suits were chosen for an office and the knitwear for weekends with a family. Very little of it was picked with a first dinner in mind, and a good part of it no longer fits the body that has to wear it.
Clothes Sized for a Previous Decade
In a 2022 OnePoll survey of 2,000 British men, 20% admitted to keeping ill-fitting clothes on the chance of getting back into them one day. Respondents also spent an average of £290 a year on clothing they never wore. A wardrobe stocked on those habits contains a large share of garments in the wrong size, and a man who has been married for 25 years has had a long time to collect them.
With age the shoulders narrow and the waist moves, so a shirt that fitted well at 45 can hang loose across the back at 60. An alterations tailor can take in a shirt or shorten a sleeve for far less than the price of a new garment.
Office Clothes at Dinner
Many men who return to dating own more work clothes than anything else, and the default is to wear them. A navy suit and a tie at a wine bar on a Saturday evening looks like the outfit of a man who came straight from a meeting. Removing the tie and replacing the suit trousers with chinos, while keeping the jacket, produces something that looks chosen for the occasion. A sports coat over an open-collared shirt is the usual middle ground for a weekend dinner, and most men already own the pieces. The opposite error is the weekend uniform of a fleece and cargo shorts. Those are clothes for a trip to the hardware store, and they look out of place at a restaurant table.
Dressing to Look Twenty Years Younger
Distressed jeans and slogan T-shirts are the usual choices of a man who wants to look younger than he is. On a man of 60 they draw attention to the age gap they were bought to hide, because the clothes and the face no longer belong to the same decade.
The woman across the table already knows his age. Anyone who agrees to a second dinner with a man of 58 has decided she is comfortable dating an older man, so clothing that pretends otherwise works against the evening. A well-cut jacket in his own size looks better on him than anything borrowed from his son’s generation.
Shoe Condition
A University of Kansas study published in 2012 asked 63 students to look at photographs of 208 pairs of shoes and judge the owners’ age, gender and income from the pictures alone. Shoes that were worn but kept spotless tended to belong to the most conscientious owners, according to the researchers.
A 15-year-old pair of brown brogues can be resoled and polished for a fraction of the price of a new pair, and new laces cost very little. Suede and pale leather show scuffs and water marks sooner than polished dark calf, so one good pair of dark brown or black leather shoes is easier to keep presentable.
Scuffed toes and worn-down heels are visible from the other side of a restaurant, and they are among the first details a date sees when he stands up to greet her.
Trouser Length and Waistband Height
Trousers that pool on top of the shoe are a common result of buying by waist size alone. Many off-the-peg trousers are sold long so that a shop can hem them, and plenty of men never have it done. A slight break, where the hem touches the shoe and folds once, is the conventional length for suit trousers. Chinos and jeans look neater with little or no break at all.
A man whose weight has moved to his stomach often wears his trousers below it, which lets the shirt bunch over the belt and makes the legs look shorter. Trousers sized for the real waist, held up with side adjusters or braces, stay at the height they were cut for and keep the shirt flat.
Fragrance Quantity
A man who has worn the same cologne every day for a decade often applies more of it than he once did, because he can no longer smell it on himself. Nose blindness, the tendency to stop noticing a familiar scent, is the usual cause. Everyone else in a small restaurant can still smell it at full strength.
A fixed number of sprays, kept the same however faint the scent seems to the wearer, solves the problem. An eau de parfum contains more fragrance oil than an eau de toilette, so a man who switches to the stronger version should use fewer sprays than before. Applying it 15 minutes before leaving the house also gives the alcohol time to evaporate.
Colour Choices
A man dressing for a date often reaches for the safest colour he owns, which tends to be navy or grey. In 2010, psychologist Andrew Elliot of the University of Rochester published research on men wearing red, with participants in the United States, England, Germany and China. Women rated men shown in red as higher in status and more attractive, and the result was consistent across the four countries. The participants were undergraduates, so the study says little about how a woman of 55 judges a man of 60.
A burgundy knit or a deep red shirt under a navy jacket is a modest way to test the idea without wearing anything loud.
Tailoring for an Ageing Frame
Men lose about 3% to 5% of their muscle each decade after 30, a gradual muscle loss called sarcopenia that becomes more noticeable around 60. The chest and arms that filled a shirt at 40 fill less of it 20 years later, and the spare fabric gathers at the waist and the small of the back.
Psychologist Ben Fletcher has written about how fast first impressions from clothes form. In one study he described, viewers who saw a man in a tailor-made suit for 3 seconds, with his face pixelated, rated him as more confident and more successful than the same man in an off-the-peg suit. The two suits differed only in small details of cut. A tailor who alters an existing jacket or shirt to the current shape of the body gets a man part of that result for much less money than a bespoke suit.
A Fitting a Week Before the Date
The most useful thing a man can do before a first date is try on the complete outfit he plans to wear, shoes included, a full week ahead. Anything loose at the collar, long in the sleeve or tight across the stomach goes to a tailor that afternoon, and most alterations are ready within a few days. The date then begins with clothes that fit the man he is now, chosen on purpose and in good repair.
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