How Older Men Can Dress for Dates With Fashion Conscious Women

In January 2022, Jeff Goldblum closed Prada's men's show in Milan at the age of 69. He walked the runway in a long dark overcoat with a fur-trimmed collar, part of a collection that Miuccia Prada and Raf Simons built around sturdy outerwear and work clothes, cast with actors the designers described as real men and recognized figures. The coat suited his age and was current at the same time. A man over 50 dressing for a date with a woman who follows fashion can aim for the same result, clothes that fit the man he is now and still look as though they were bought this decade.

Fit and Proportion

Weight and posture change after 50, and clothes bought for an earlier body show it. The shoulder seam of a jacket should be at the edge of his shoulder, and the sleeve should leave a little shirt cuff visible. Trousers should touch the shoe with little or no fold, and a shirt collar should close without gapping or squeezing, since the neck is in view across a table all evening. A shirt that pulls across the stomach or billows at the back looks worse than a cheaper shirt that fits. Taking in a jacket waist and hemming trousers are routine jobs for a tailor, and they cost a fraction of what a new garment would. Asking the tailor to check the jacket while he wears the shirt he plans to wear on dates gives a more accurate fit. A woman who follows fashion will notice the result even if she cannot say what changed. A man who has worn a large shirt for 20 years may now need a medium in the shoulders and a different cut through the middle, and trying on two sizes of the same item in the store settles the question faster than relying on habit. Trousers should be checked too, since a waist that has to be held up with a tightly cinched belt bunches the fabric and makes the whole outfit look borrowed.

Age and Current Style

Some men over 50 keep wearing the cuts they bought in the 1990s, and others borrow the wardrobe of their sons. Women who are open to dating older men often cite maturity and stability among their reasons, and clothes copied from men in their twenties undercut both impressions. Current cuts in classic forms avoid both mistakes. A trouser with a slight taper and a jacket that ends at the seat are current cuts that men of any age can wear. Heavy logos and distressed denim are the first items to retire. Frames for glasses bought ten years ago date a face quickly, and an optician can suggest current shapes in a single visit.

Color Choices for a First Date

Across seven experiments led by Andrew Elliot at the University of Rochester, women in the United States, England, Germany, and China rated photos of men. A man pictured in a red shirt was rated more attractive, more sexually desirable, and higher in status than the same man shown in white, gray, green, or blue. Red did not make him seem more likable or kind, and the women did not appear to notice the color's effect on their judgments. Elliot said the findings suggest that the link between red and sex also applies to men, which gives an older man a simple reason to wear red on a date in small amounts. A burgundy knit or a dark red pocket square adds the color in a small dose. Navy and charcoal remain dependable base colors for an older man, since both work with gray hair and most skin tones, and a woman who follows fashion will see a navy jacket over a burgundy sweater as a deliberate choice. A small check or fine stripe on a shirt adds interest up close, while a large bold print looks loud across a dinner table.

Jackets and Made-to-Measure Suits

Tailoring changes what people assume about a man within seconds. In a University of Hertfordshire study, more than 300 people viewed images of a man for three seconds each, with his face hidden. When he wore a made-to-measure suit, viewers judged him more confident, more successful, more flexible, and a higher earner than when he wore a similar off-the-peg suit. The research was carried out with a tailoring firm, which gives the result a commercial sponsor. The two suits differed only in small details of fit, and an older man on a budget can reproduce most of those details through alterations. An unstructured navy jacket from a good retailer, adjusted by a tailor at the waist and sleeves, gets most of the way there and works over a shirt or a fine sweater. A wool or wool-blend jacket keeps its shape through an evening better than a polyester one. In cooler months, a plain wool overcoat in navy or camel is the first thing she sees at the door, so it is worth buying one that fits over a jacket.

Shoes and First Impressions

Researchers at the University of Kansas asked a group of students to judge people by their shoes using photos alone, and the students guessed the owners' age, sex, and income better than chance. A survey commissioned by the shoe brand Allen Edmonds found that 64% of women judge a man's fashion sense by his shoes, a figure that comes with an obvious commercial interest.
Brown suede or leather loafers and desert boots suit most date settings, and a minimal white leather sneaker is fine for coffee or a gallery visit if it is spotless. Scuffed toes and worn-down heels are the details a fashion conscious woman sees when she glances down, and a cobbler can replace heels on a good pair for far less than a new pair costs. Socks should match the trousers or add one quiet color, and no bare shin should show when he sits down.

Grooming and Fragrance

Rachel Herz, a Brown University cognitive neuroscientist known for her research on the psychology of smell, published a 2002 paper with Michael Inzlicht on the importance of smell for women in choosing a partner. In their survey of 198 college students, women ranked body odor as more important for attraction than looks. Natural scent mattered most, so cologne should be light, one or two sprays applied well before he leaves the house. A fresh haircut and trimmed eyebrows cost little and are noticed at a dinner table, where she will spend an hour about three feet from his face. Nose and ear hair should be gone, and nails should be clean and short, since his hands are in view for the whole meal. Gray hair looks intentional when it is cut shorter at the sides and trimmed every few weeks.

A Saturday Dinner at Eight

He arrives at the restaurant five minutes early in a navy jacket taken in at the waist, an open-collar white shirt, dark trousers that touch the tops of polished brown loafers, and a single spray of cologne applied an hour before. She sees the fit first, then the shoes, and by the time the menus arrive neither of them is thinking about his clothes.