On a first date, wear what you would wear on a good day, one step smarter. For most first dates in the UK that means dark trousers or jeans, a knit or a shirt that fits well, clean shoes and one good outer layer. The venue decides the rest.
Three rules for every first date
- Fit first. A plain jumper that fits beats an expensive one that does not.
- Dress for the venue, plus one step. Slightly overdressed reads as effort; underdressed reads as indifference.
- Wear something you have worn before. A first date is not the night to find out that new boots rub.
Outfits by venue
Drinks at a bar or pub
Dark jeans, a fine roll neck or a knitted polo, and Chelsea boots. Add an overshirt or a short jacket. See roll neck jumpers and jeans.
Dinner at a restaurant
Tailored trousers, a shirt or a fine knit, and a blazer you can take off. Loafers or leather boots. See blazers and trousers.
Coffee or a daytime walk
Chinos or dark jeans, a quarter-zip or crew neck over a T-shirt, and smart trainers. See quarter-zip jumpers and smart trainers.
An activity date
Bowling, mini golf or a gallery: dress as for coffee, and make sure you can move. Avoid anything stiff or precious.
A winter evening
Any of the above under a long overcoat, with a scarf. The coat is the first thing your date sees, so it is worth getting right.
Colours that work
Navy, charcoal, cream, olive and burgundy are all flattering in evening light. Keep to two or three colours in the outfit. Black is fine, but all-black can look severe in a bright café.
The details people notice
- Shoes. Clean them. Scuffed shoes undo the rest.
- Ironing. A creased shirt is the most common avoidable mistake.
- Fragrance. One or two sprays, no more.
- Hands. Clean nails; a simple watch if you wear one.
What to avoid
- Gym wear, football shirts and anything with a large slogan.
- Brand-new clothes you have not tested for comfort.
- A full suit, unless you are coming from work or the venue calls for it.
Questions answered
Should I wear a shirt on a first date?
A shirt is always safe for dinner. For drinks or coffee, a fine knit or a knitted polo is equally smart and more relaxed. See knitted polos.
Are jeans acceptable on a first date?
Yes, if they are dark, clean and fit well. Pair them with boots or loafers, not running trainers.
What should I wear on a first date in winter?
A roll neck, dark trousers, boots and an overcoat. It is warm, it is smart and it works in every venue.
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