Comfort first
What to Wear on a First Date: Easy Outfit Rules
Wear what you feel good in, fit it to the plan and the weather, and stop second-guessing the mirror.
Wear something you already feel good in, one notch smarter than the place you are going, that suits the weather and the plan. Fit and comfort beat fashion. Shoes you can walk in, a layer for the cold and a light touch of scent are the details that matter most.
Rule one
Comfort and confidence come first
The best first date outfit is one you have already worn and felt good in. Time Out London’s first-date style tips, written with the fashion site Lyst in 2015, make the same point: wear styles you already feel at home in, and if you fancy something new, make it an accessory. You are less likely to fidget with a bag or a piece of jewellery than with a new top.
If you keep adjusting it, it is the wrong outfit.
Try the sit-down test before the day. Sit, bend, reach and climb a flight of stairs in the whole outfit. If you notice it, change it. Confidence is hard to fake in shoes that pinch.
Rule two
Dress for the plan and the weather
Aim one notch smarter than the venue. Not sure what you will be doing? Hedge. Time Out London suggests the middle ground, such as a shirt and a nice pair of jeans, and nothing too restrictive: stumbling round a mini-golf course in stilettos is, in its words, “not cute”.
- Coffee or a walk. Smart jeans, a good top and shoes that can manage a mile.
- Pub or bar. One notch up: a good shirt or top, dark trousers, clean boots.
- Gallery or market. Light layers, because indoors and outdoors rarely match.
- Anything active. Clothes you can move in. Ask what the plan is.
Then look outside. The Met Office calls autumn often unsettled and stormy and summer the most thundery season, while spring is often calm and dry, so a waterproof earns its place in more months than you might think. Check the forecast the day before and again that morning.
Your wardrobe
What should men, women and everyone else wear?
Most advice splits by gender. These cards split by what you actually put on, so take the one that fits your wardrobe.
Shirts, knits and trousers
A shirt that fits across the shoulders or a good knit, with chinos or dark jeans and clean boots or leather trainers. Iron it, roll the sleeves if it is warm and skip the novelty slogan.
Dresses, skirts and tops
Choose a dress or skirt you can walk, sit and climb stairs in, with tights or boots when it is cold. Unsure of the plan? Time Out London says trousers are probably the safer option. Wear heels only if you wear them often.
Anything that is yours
Wear whatever feels like you on a good day. The same rules apply: fit, comfort, weather and plan. You do not have to look like anyone’s idea of a date.
Fit and colour
Colours and fit that flatter
Fit does more for you than a price tag or a label.
- Fit beats price. A cheap shirt that fits looks better than an expensive one that does not. If something pulls, gapes or slides, leave it at home.
- Wear a colour you have been complimented in. It will make you stand a little taller.
- Start neutral, add one bright thing. Time Out London says a bright colour or bold pattern is fine if you are at ease in it.
- Mind the stains. A white shirt and a bowl of pasta are a risky pairing, which is one more reason to skip dinner.
- Check it in daylight. Bedroom bulbs flatter nobody and lie about colour.
Quick rules
Do this, skip that
Do
- Wear shoes you can walk a mile in.
- Bring a layer for the way home.
- Iron or steam what you wear.
- Keep scent subtle, or leave it out.
- Pick one detail that feels like you.
Skip
- Brand-new shoes you have not broken in.
- A strong scent in a small room.
- Anything you keep tugging or tucking.
- A slogan that starts an argument.
- Dressing for a different date from the one you are on.
Plain English
Dress-code words, decoded
Wikipedia itself calls smart casual “an ambiguously defined Western dress code”, so treat these as guides, not laws.
- Casual
- Clothes you would wear to the shops: jeans, a jumper, trainers. Fine for a walk, with a clean top and tidy shoes.
- Smart casual
- The safe default for a first date. Neat and fitted, with no sportswear: dark jeans or chinos, a shirt or good knit, clean trainers or boots.
- Business casual
- A work code: a collared shirt or blouse, trousers or a skirt, closed shoes. A bit formal for a first date unless you are coming from the office.
- Dressy casual
- A step above smart casual. A dress or a blazer, still no tie. Right for a nice bar or an evening at a gallery.
- Cocktail attire
- Evening dressing: a cocktail dress, or a suit with or without a tie. It is for a party invitation, not a first coffee.
- Venue rules
- Some places set their own rule about trainers or sportswear. Check the venue’s website before you go.
Before you leave
The last-minute checklist
- Phone charged and a way home sorted.
- A layer or an umbrella, per the forecast.
- Shoes clean and comfortable.
- Teeth brushed, mints in a pocket.
- Scent light, or none.
- Keys, card and tissues in your pockets.
- Nothing you will keep adjusting.
- The place and time shared with a friend.
Still choosing where to go? Our first date ideas and daytime date ideas help, and the date ideas hub leads to city pages, such as date ideas in Birmingham, that name real places. For the safety side, see how Forget Dinner keeps things safe.
First date outfit questions, answered
What should I wear on a first date if I do not know where we are going?
Go for the middle ground: dark jeans or tailored trousers, a good shirt, knit or top, and shoes you can walk in. Add a layer that works indoors and out. That combination suits a coffee, a pub, a market or a gallery without looking over- or under-dressed.
Is it okay to wear jeans on a first date?
Yes, if they fit well and are clean and unfrayed. Dark, plain jeans with a smarter top pass for almost any first date short of a formal restaurant. Skip ripped, faded or very tight pairs, because you will be sitting, walking and reaching in them.
What colour should I wear on a first date?
Wear a colour you have been complimented in. Mid-tones and deep shades hide small stains better than white or pale colours. If you want to stand out, add one bright piece rather than a whole outfit of it.
What should I wear on a first date in my 40s?
The same rules apply: fit, comfort and clean shoes. Dress for the person you are now, in cuts that move with you, rather than chasing a trend. Good basics in colours you like will do more for you than anything fashionable this season.
How dressed up should I be for a first date at a pub?
One notch above the pub. A good shirt or top and clean shoes will do. You want to look as if you made a small effort, not as if you came from a wedding or the gym.