What to wear on a first date at 50: kept simple

Wear what you would wear to meet a friend you wanted to impress, then take it one notch up, not three. Dress for the café or pub you are actually sitting in rather than for an imaginary gala, wear shoes you have already walked half a mile in, and buy nothing brand new on the morning of the date. That is ninety per cent of the problem solved. Below is the rest: how daytime and evening outfits differ in Britain, why your profile photos matter more than your jacket, two foolproof combinations already hanging in your wardrobe, and a ten-minute checklist before you leave the house.

The one rule

You already own the right outfit, because you have worn it before. Picture what you put on when you are meeting an old friend in town for lunch and want to look well: clothes that fit your shoulders properly, a colour people compliment you on, and nothing you have to keep tugging down or unbuttoning when you sit.

For a first date, take that exact outfit and move it up one notch: the clean suede boots instead of the dog-walking trainers, the pressed linen or Oxford shirt instead of the washed-out polo, the good coat. Moving it up three notches is where people go wrong. Turning up to an eleven o’clock flat white in a three-piece suit or cocktail silk makes both of you feel as if you are conducting a job interview in Costa.

Dress for the venue, not the occasion

“A first date” is not a place with a dress code. A Tuesday morning coffee in a gallery café, a Sunday walk along a canal towpath, and a Thursday drink in a quiet pub are three real places, and you already know how to dress for all three. Find out where you are meeting first, picture the tables at that hour of the day, and dress to match the room.

Daylight meetings call for the relaxed half of your wardrobe: dark jeans or chinos or a skirt you can stride in, a soft jumper or blouse, and a coat that folds over the back of a café chair without taking up the next table. Evening meetings take the same silhouette half a shade darker and smarter, with one crucial British addition: a layer you can take off. British pubs and restaurants are either tropical or draughty, and walking back to the station in October is a third climate altogether. If you have not settled on where to meet yet, first date ideas for over 50s has sixteen daytime and early-evening options that take the pressure off.

The shoe test

Whatever pair you plan to wear, put them through a simple rehearsal the day before: walk briskly in them for twenty minutes, then stand still on a hard floor for ten. First dates involve far more standing and walking than people picture when they are dressing in front of the bedroom mirror. There is the station platform, the walk from the car park, the cobbles outside the market, and the ten-minute chat by the door when neither of you quite wants to leave yet. A shoe that only behaves while you are sitting down will ruin your concentration by quarter to twelve.

What photographs well, and what reads well across a table

Nobody takes portraits on a first coffee, though it helps to know how light behaves on fabric. Across a café table by a window, texture and colour near your face do all the work. A soft knit, a clean collar, a scarf or a shirt in a shade that brings out your eyes reads as warm and approachable immediately.

The clothes that actually get photographed are the ones in your dating profile. On a dating site, hundreds of members will judge your profile pictures long before anyone sees what you wear to a café, so if you are going to spend twenty minutes fussing over a shirt, do it on the afternoon a friend takes your profile photos. Joining and browsing cost nothing: you can make a free profile and see what people your age actually wear in their pictures.

A short checklist before you leave

Run down these five in order on the day before and the morning itself:

1. Check the venue and the rain radar. Turning up soaked because you refused to carry an umbrella never made anyone look dashing.
2. Start from your trusted friend-lunch outfit, one notch up. If you look in the mirror and feel as if you are wearing someone else's clothes, take one smart piece off.
3. Pass the shoe test the day before. Twenty minutes walking, ten standing. If you feel a pinch in the hall, you will feel a blister by the main course.
4. Wear a layer you can shed. A cardigan, blazer or light jacket over a shirt or top lets you survive both a roaring pub fire and the platform home.
5. Sit down in front of the mirror once. Café chairs are low; check that buttons, waistbands and hems behave when you are seated, not only when you are standing straight.

What not to buy

Do not buy a brand-new outfit on Friday afternoon for a Saturday morning coffee, and above all never wear brand-new shoes on a first date. New shoes spend their first two outings breaking in your heels, and stiff new collars have a habit of scratching your neck just as you are trying to listen to someone’s story. If you genuinely want a new shirt or jumper to lift your confidence, buy it a fortnight ahead and wear it twice round the house and to the shops first.

The other thing not to buy is the notion that you have to dress twenty years younger than your birth certificate. Every member on SilverSingles is at least 50 under the service agreement, which means the person walking through the café door is in their fifties, sixties or seventies too. Clothes that try to disguise your decade always look like hard work; clothes that fit you well today look like self-possession.

One for daylight, one for evening

Almost every British first date falls into one of two simple formulas you can pull straight from your rail:

For a daytime coffee, gallery or walk: dark well-cut jeans, chinos or a comfortable midi skirt; a plain shirt, Breton top or fine knit in a colour that suits your skin; a jacket or trench coat that handles a shower; and flat leather boots, loafers or clean smart trainers you can walk two miles in.

For an early-evening drink or supper: dark tailored trousers or a simple dress you already love; a crisp button-down shirt or silk-blend blouse; a proper unstructured blazer or smart cardigan; and the same tested boots or low heels.

If your first outing is an organised evening rather than a one-to-one coffee, remember that speed dating and singles events for over 50s involve two hours of moving between tables in a warm room. Dress half a notch cooler and in your most forgiving shoes.

Grooming, briefly

Wear your hair the way you normally wear it on a good day rather than experimenting with a new cut three hours before meeting. Clean fingernails, a pressed shirt, clean glasses, and one light spray of whatever scent you usually wear (not three). Twenty quiet minutes with the iron the night before does more for how you come across than any amount of shopping.

Questions people ask