For a first date, wear clean, well-fitting clothes that suit the venue and feel like you. A decent shirt with good jeans works for many relaxed evenings; a smarter restaurant may call for a jacket. Comfort, grooming and a little effort beat an outfit that makes you feel as though you're playing another man.
The trouble with getting dressed for a first date is that the wardrobe suddenly becomes full of clothes you've apparently never seen before.
That shirt? Too dull. The other shirt? Too loud. The good jeans have developed a mysterious crease. The expensive jacket now looks as though it belongs to your uncle, the one who owns three sports cars and refers to himself in the third person.
Before long you're standing in your bedroom wearing one shoe, wondering whether a man can be romantically disqualified for choosing the wrong shade of blue.
Gentlemen, it's time for a little order.
What to wear on a first date depends on where you're going, the weather and the version of yourself you're happiest presenting. The goal is to show that you've made an effort without looking as though you've been kidnapped by a menswear catalogue.
A well-chosen outfit can help you feel at ease. It cannot manufacture chemistry, replace manners or compensate for spending dinner explaining your entire investment portfolio. Clothes have their limits, however beautifully pressed.
Find out where you're going before deciding what to wear
A woman agrees to meet you for coffee on a Sunday afternoon. Excellent. You arrive in a dinner jacket. She arrives in jeans and a jumper. Both of you are now wondering whether you've come to the same event.
Start with the venue. Is it a casual café, a smart restaurant, a pub, a walk through the countryside or an activity where somebody might have to bend over, climb a wall or throw an axe?
Check the restaurant's dress code if there's any doubt. If the plan includes walking between places, think about the shoes and coat, not just how you look under flattering indoor lighting.
Being appropriately dressed tells her you have understood the occasion. More importantly, it gives you the freedom to concentrate on the person rather than on whether you'll be refused entry or fall into a flower bed.
You don't have to buy a single new thing. In most wardrobes there's an outfit waiting to be rescued from poor combinations and a shirt that desperately needs an iron.
For coffee: relaxed, tidy, and definitely not dressed for bed
Coffee dates tend to be informal. That's part of their appeal. You can sit together for an hour, discover whether you get on and escape before either of you feels trapped in a three-course commitment.
For most men, a clean, well-fitting T-shirt under an overshirt or casual jacket works nicely with dark jeans or chinos. Alternatively, a fine knit jumper looks quietly put together without trying too hard.
As for shoes, tidy trainers can be absolutely fine in a casual café. Clean is the important part. Those old white trainers that have turned the colour of weak porridge after three winters of abuse might deserve a rest.
Avoid dressing so carefully that you're frightened to sit down. A pair of trousers that requires you to exhale before fastening them is not a romantic investment. It's a health and safety concern.
The impression we're after is simple: you usually look after yourself, and today you've bothered to do it properly.
For drinks at the pub: smart-casual with a bit of character
The British pub is a splendid first-date setting because it lets a gentleman look well dressed without resembling a junior minister arriving to announce funding for the bypass.
Try a good Oxford shirt or textured knit with chinos or dark denim. Chelsea boots, neat leather shoes or clean understated trainers can all work, depending on the place.
A lightweight jacket can make an otherwise simple outfit feel considered. A suede-style bomber, a smart overshirt or an unstructured blazer has more personality than an anonymous black coat dragged from the hallway.
Don't obsess over whether the shirt should be tucked in. If it is cut like a casual overshirt, leave it as intended. If it is a dressier shirt with a long curved hem, tucking may look better. Try it before you leave rather than adjusting it continuously beside the bar.
And if the pub is the sort of place where everyone wears walking boots because they've come straight off a hill, let the surroundings guide you. Looking appropriate is more charming than looking expensive.
For dinner: raise the standard, not the volume
A nicer restaurant is the moment for a little polish. Not peacocking. Polish.
Well-fitting tailored trousers or dark, smart denim, a crisp shirt or elegant knit, and proper shoes create a strong foundation. An unstructured blazer adds something if the restaurant calls for it. A plain shirt in white, pale blue, deep navy or a flattering earthy shade is often more useful than a complicated pattern trying to stage a fireworks display across your chest.
If you're wearing a jacket, check the shoulders and sleeves. The buttons shouldn't pull when you sit. The collar shouldn't bunch behind your neck. The trousers shouldn't pool in fabric around your ankles as though the tailor has left spare material for future generations.
A tie is rarely necessary unless the venue's rules make one appropriate. If a restaurant is smart enough to demand formalwear, dress for it. Otherwise, a sharp shirt and excellent fit usually carry you further than decorative extravagance.
One last thing: if you're meeting after work, don't assume your office outfit has survived the day with its dignity intact. Give it a quick inspection before heading out. Lunch is remarkably good at leaving evidence.
Walking and activity dates require common sense
A woodland walk demands something rather different from cocktails in Mayfair. Wear shoes that can cope with the route, layers appropriate for the weather and clothes you can move in comfortably.
If you're going bowling or playing mini golf, a smart casual combination is usually fine. If you're rock climbing, hire the appropriate equipment and wear clothes that move with you. There's no prize for being the best-dressed gentleman halfway up the climbing wall while unable to lift his knee.
For a summer outdoor date, breathable fabrics and a sensible light layer can help. British weather remains committed to the element of surprise, even when the forecast has sworn it will behave.
Don't choose new shoes for a long walk just because they look wonderful in the box. Blisters are an appalling third wheel. Wear something you've already tested.
The most stylish outfit in the world is a failure if you spend the date fidgeting, shivering or trying to hide the fact that you can no longer feel your toes.
Fit matters more than the label inside the collar
Here is one of menswear's kinder truths: you don't need to spend a fortune to look good.
A modestly priced shirt that fits your shoulders, chest and waist will generally look better than an expensive one hanging from you like a spare bedsheet. The same applies to trousers. They should allow you to sit comfortably, fall neatly and give your shoes a fighting chance of being seen.
Try your full outfit on before the date. Sit down in it. Walk around. Lift your arms. Check it under ordinary daylight as well as the forgiving glow of your bedroom lamp.
If the sleeves are too long or the trousers need a simple alteration, a tailor may offer more benefit than an entirely new purchase. But don't embark on a wardrobe reconstruction the afternoon before dinner.
And don't copy a fashion photograph without considering your own proportions, personality and the climate. A linen shirt worn open over a vest may look marvellous on a man posing beside the Mediterranean. Outside a Yorkshire pub in February, it can suggest a lost holidaymaker in urgent need of help.
Grooming: the small details people actually notice
Your clothes can be excellent and still be let down by the simplest things.
Clean fingernails. Fresh breath. Hair and facial hair cared for in your usual style. A shirt that doesn't smell of damp laundry. Shoes that haven't been used to excavate the garden.
Nothing revolutionary. Just the signs of someone who pays attention.
If you wear fragrance, keep it restrained. One person's lovely scent is another person's migraine waiting to happen, particularly in a small restaurant. Your date should notice you before the perfume arrives at the table.
Don't debut an adventurous new haircut or shaving routine five minutes before leaving. It is a first date, not an experimental dermatology conference.
And put something in your pockets without ruining the outline of your trousers. A wallet, keys and phone are enough. You do not need to carry an emergency warehouse of miscellaneous objects in your jacket.
Show some personality, but avoid becoming the entertainment
This is where a man can have a little fun.
Perhaps you wear a brilliant watch inherited from your grandfather, a colourful scarf, a distinctive jacket or boots with a bit of character. A single interesting touch can make an otherwise simple outfit feel genuinely yours.
If bold clothes are already part of your personality, don't suddenly disguise yourself in beige to satisfy imaginary dating rules. On the other hand, don't wear something flamboyant purely because a stranger on the internet promised it would make you irresistible.
A woman is meeting a person, not a carefully constructed costume. If you always dress in beautifully cut dark clothes, wear those. If you're happiest in good denim and a cheerful shirt, find the smartest version of that combination.
Wear the outfit rather than allowing it to wear you. You should be able to laugh, lean back, walk through the door and forget about the clothes for a while.
That is when style becomes genuinely attractive: when it stops demanding attention every twelve seconds.
Five-minute check before you leave
I appreciate that no gentleman wishes to conduct a military inspection in his hallway, but a quick glance saves a great deal of unnecessary embarrassment.
Check that the clothes are clean and fit as they should. Check the shoes. Check whether the venue is smarter than you first thought. Look at the weather. Make sure your phone is charged and your pockets contain what you'll actually need.
Then stop fussing.
There is a point at which repeated mirror inspections achieve nothing except making you late. If you've chosen appropriately, made an effort and can move comfortably, the job is done.
You've dressed for the evening. Now go and have one.
Monty's verdict: she should remember the man, not his shirt
Your best first-date outfit is not necessarily your most expensive, fashionable or daring. It's the one that suits the occasion, flatters you and leaves you comfortable enough to be present.
Match the venue. Respect the weather. Pay attention to fit and grooming. Include a little individuality. Leave the costume department to the theatre.
Then forget about the buttons, seams and shoe leather and concentrate on enjoying the woman you've come to meet.
Because if the evening goes splendidly, the loveliest thing she might say afterwards isn't, “What a magnificent pair of trousers.”
It's, “I'd really like to see him again.”