What should a man wear on a first date?
Dress one step smarter than the place. If everyone at the café will be in T-shirts, wear a good shirt. If the restaurant is smart casual, add a jacket. The aim is to look as though you made an effort without looking as though you are attending a meeting.
Three things do most of the work: clothes that fit, shoes that are clean, and a quiet palette of two or three colours. None of them costs much, and all of them are noticed.
What to wear, by where you are going
| The date | What works | Shoes |
|---|---|---|
| Coffee or brunch | Dark jeans or chinos, an oxford or linen shirt, or a plain knit polo | White leather sneakers or loafers |
| Dinner at a good restaurant | Tailored trousers, a crisp shirt open at the collar, an unstructured jacket | Loafers or suede derbies |
| Drinks or a rooftop bar | Dark trousers or jeans, a dark shirt or fine roll-neck, a jacket for later | Suede boots or loafers |
| Daytime walk, museum or market | Chinos, a short-sleeved camp-collar shirt or a polo | Clean sneakers |
| Fine dining or an anniversary | A suit without a tie, or a jacket and trousers in contrasting colours | Polished oxfords or loafers |
| Dinner at home | Good trousers and a knit or a soft shirt. Relaxed, but not the clothes you slept in | Clean indoor shoes or smart slides |
Is a suit too much for a date?
Usually, yes. A full suit and tie can read as nervous or as though you have come straight from work. The exception is a formal restaurant or a special evening, and even then, lose the tie. The easier move is a jacket worn as a separate: an unstructured linen jacket over a shirt or T-shirt looks relaxed and deliberate at the same time.
Jeans or trousers?
Dark, slim-straight jeans with no rips work for most first dates. For dinner, trousers look more grown up. A pleated trouser in cotton or linen, like the Cadogan, sits between the two: smarter than jeans, easier than suit trousers.
What colours work best?
- Navy, white and grey: the safe, flattering base.
- Olive, tobacco and chocolate brown: warmer, and very good on Indian skin tones.
- Soft blue and sage for daytime.
- Black for evening drinks, as long as it is not head to toe in one flat shade.
One colour can be bold. Two bold colours start to compete with your face, which is the part of you the other person is looking at.
Fit matters more than the label
- The shoulder seam ends where your shoulder ends.
- A shirt sleeve stops at the wrist bone, and a jacket sleeve shows about a centimetre of shirt cuff.
- Trousers sit on the shoe with little or no fold. Fabric pooling at the ankle makes anyone look shorter.
- A shirt should not pull across the buttons when you sit.
A well-cut ₹4,000 shirt looks better than a loose designer one. A shirt made to your measurements is the cheapest way to look expensive.
What not to wear
- Gym clothes, shorts to dinner, or flip-flops anywhere but a beach.
- Large logos and slogan T-shirts.
- Something brand new you have never worn. Test it first, so you are not adjusting a collar all evening.
- Too much scent. One or two sprays, not a cloud.
Small things people notice
- Clean shoes, and a belt that matches them.
- Trimmed nails and a tidy neckline.
- A simple watch rather than several accessories.
- A jacket in the car for a place that turns out smarter than expected.
Second dates and beyond
Keep the same level and vary the pieces. If the first date was a jacket and jeans, the second can be a knit and trousers. For a birthday or anniversary dinner, step up once: a suit without a tie, or a Nehru jacket over a crisp shirt.
Questions, answered
Not for dinner, drinks or anywhere with table service. An unstructured jacket over a shirt or a fine knit looks considered without looking like you came from the office. For coffee or a walk, leave it at home.
Yes, if it is plain, well fitted and in good condition, and the place is casual. Under a jacket, a white or navy T-shirt is one of the easiest date outfits there is.
Dark, well-fitted jeans work for most first dates. Trousers in cotton, linen or light wool are the better choice for dinner at a good restaurant.
Navy, white, olive, earth browns and soft blue. They flatter most skin tones in India and photograph well. Avoid loud logos and more than one bright colour at once.
Tailored trousers, a crisp shirt and a jacket, with loafers or suede derbies. No tie unless the restaurant is formal.
