What to Wear on a Date as a Man Over 40

Dress one step above the place you are going, make sure everything fits you, and drop anything that is ten years out of date. At 40 and beyond you want to look like a man who has his life together, not like a teenager and not like someone who stopped updating. A dark pair of jeans or trousers, a good shirt or knit that fits, and clean shoes cover most dates. That also answers what to wear for date night: the same pieces, one notch sharper.

a dating coach describes two kinds of older man. One is worldly, successful, and put together, and the other has only gotten older. Your clothes are among the first things a woman reads. You want her to place you in the first group.

That does not mean spending a lot. It means choosing clothes that suit your age, your build, and the place you are going. My advice is to dress in a way that is elegant, stylish, and appropriate for a successful, sophisticated, slightly older man. It also means two things you can control without any shopping: do not dress like a 20-year-old, and do not wear clothes from a decade ago.

Look at where you are going and then dress slightly above it. A casual coffee shop is a good reason to wear a clean knit and nice jeans, not a faded t-shirt. A bar or restaurant is a good reason for a collared shirt or fine knit and a jacket if you have one.

Why one step: a woman who walks in and sees you dressed as if you made an effort feels that you took the date seriously. Over-dressing by a lot makes you look stiff, and under-dressing makes you look careless. One step above sits right.

A cheap shirt that fits at the shoulders looks better than an expensive one that does not. Check these:

• Shoulder seams sit at the edge of your shoulders.
• Sleeves end at the wrist, not over your hands.
• Trousers and jeans have a clean break at the shoe, without a pile of fabric.
• Nothing pulls across the chest or stomach.

A tailor can fix most of these cheaply, and it changes everything you wear. If you spend money before a date, spend it there.

For most men over 40, a short list works best:

• Daytime or coffee: dark jeans or chinos, a plain shirt or a crew or quarter-zip knit, clean shoes or boots.
• Drinks or dinner: dark jeans or trousers, a collared shirt or fine knit, a jacket or blazer that fits, leather shoes or clean minimal sneakers.
• A nicer evening: tailored trousers, a good shirt, a jacket, and polished shoes.

Choose solid colors that suit your skin and hair, such as navy, gray, olive, white, and black used with care. Skip loud logos and busy prints. They pull attention from your face and age quickly.

Go through your closet and cut the things that mark you as stuck in an earlier time:

• Clothes with worn collars, stretched necks, or faded color.
• Baggy cargo shorts, graphic tees, and sports jerseys.
• Shoes that are scuffed, worn at the heel, or noticeably old.
• Jeans with the wrong cut or the wrong fade for your age.

You do not need a new wardrobe. Replace the worst few pieces with three or four good ones you can rotate.

Clothes will not fix grooming. Before a date:

• Get a haircut you like, and keep it fresh.
• Trim your beard cleanly or shave, and tidy your eyebrows and nose hair.
• Keep your nails clean.
• Wear a light scent, not a heavy one.
• Brush your teeth and carry mints.

coach also makes the plain point that your shape matters. A man who looks 45 at 45 is better off than one who looks 65. Training a few times a week and sleeping enough will do more for how your shirt hangs than any shopping trip.

If you are unsure, ask a well-dressed friend or a female friend whose taste you trust. A department-store stylist or a tailor will help for a small cost, and many men find a single hour of help is enough to change their whole closet.

She is not scoring your brand. She notices whether you look clean, comfortable, and like you made an effort for her. Wear what makes you feel relaxed and sure of yourself, because a man who is not thinking about his clothes pays better attention to her. Get that right and everything else on the date gets easier.