What to Wear on a First Date

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Most people start agonising about what to wear the minute they’ve written First Date in their diary.

Guys worry that a t-shirt is too casual whereas a suit might be too smart while the female sex debate long and hard over whether they should wear a sexy revealing dress or stick with a pretty blouse and longer length skirt.

(Then of course there’s the accessories … high heels or not, lots of jewellery or a simple chain, tights or stockings ….. it can take a while to figure it all out.)

And while there is no single right answer to what to wear on your first date, there are some factors that certainly help in making your choice – starting with the venue.

If the date is taking place in a pricey French restaurant, then chances are you won’t be considering a t-shirt or sweatshirt and similarly, if you’re going bowling then a figure-hugging mini dress is obviously not the best option.

Next, you need to take into account the person you’ll be meeting and the time of day.

So, let’s start with the girls ….

First, check out your date’s profile and picture if you’ve arranged the date through an agency or website. Does he seem like someone who would be at ease in a pinstriped suit and gleaming brogues or the casual outdoorsy type?

(Obviously, if he lives in joggers or jeans, you’ll look an odd couple if you turn up dressed to the nines.)

Okay, you haven’t met him yet but his profile should give you some clues. For example does he say he’s looking for a sexy dance-floor partner or mention that he’s looking for a homey type who likes curling up on the sofa to watch a movie?

Next, where will you be meeting? A stylish silk dress might be perfect for a late night rendezvous in a restaurant but you could well feel just a bit overdressed if you’re meeting at lunchtime.

The most important piece of advice for any first date is to wear something that you will feel confident and comfortable with. Four-inch stilettos may make your legs look longer but if you don’t normally wear them, then you won’t feel at ease.

Do you usually wear outfits that show off a lot of skin – mini skirts or low-cut tops for example?  If not, then don’t try to be something you are not. Of course that doesn’t mean you can’t make an effort to look your best – after all, this is a first date!

So if it’s a lunchtime drink, you could opt for smart casual – black jeans and a stylish top set off by pretty shoes and a little jewellery. You won’t look overdressed – but it will be clear that you’ve put some thought into how you look.

This might also be a good outfit choice for a Drinks-then-Cinema date where you want to look good but don’t want to be stuck in an impossibly tight dress for two hours during the film.

If the date is an upmarket restaurant, then it’s time to iron that little black dress – or a variation of it at least. Smart, pretty but not overly revealing or party style.


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Other Top Tips

  • Unless this really is your usual style, make sure you avoid outfits that make you look tartish or slutty.
  • Don’t suddenly decide on a new hairstyle at the last minute – that’s inviting disaster
  • Choose an outfit that makes the most of your best features – a colour that brings out your eyes or a shaped skirt that shows your trim figure
  • ALWAYS have a dry run before the big day – you don’t want to find a missing button, broken zip or laddered stockings when you’re getting ready

A friend of mine always draws a little picture in her notebook of the “full look” to make sure she hasn’t forgotten anything. She has little arrows from each item to a description at the side where she puts details of everything from the main outfit to intended nail colour.

It’s a great idea because that way, she knows exactly what she’ll need by way of tights, nail polish, hair combs etc. (If you don’t have an artistic bone in your body, it’s still a good idea to make a list of everything you’re planning to wear.)

Finally, always aim for colours that you know work for you and styles that flatter your shape.

Don’t buy a brand new dress in a style you’ve never worn because you’ll feel self-conscious the whole time.

Now for the Guys …..

I know, girls think you have it easy – no difficult choices between short/long dress or trousers, nail colour or heels but the truth is that many guys still spend hours debating what they should wear to impress.

Again, your outfit will depend on the venue, time of day and the person you’re meeting.

This should help you to decide between a classic long sleeved shirt, preppy style or a more casual polo or t-shirt top. Teamed with stylish jeans or canvas trousers, this last one would be good for the bowling alley or a picnic in the park.

But if you’re meeting in a swish restaurant or playing the tables at a casino then you’d probably be better going for smart dark trousers and the classic shirt or even a well-cut suit.

(You can easily remove the jacket as soon as you get inside.)

If you hate the idea of a smart jacket, there’s a lot of stylish knitwear around at the moment and that’s a good choice for colder weather.

Similar to the advice for women – don’t buy clothes for a date that you aren’t likely to be comfortable with so if you’ve never worn hipster jeans, this isn’t the time to try them out.

And if you’re a little older, don’t suddenly go shopping in a trendy shop. There’s nothing worse than mutton dressed as lamb whatever your sex!

Finally make sure that shoes (and socks!) are a good match for the outfit and that your hair is neat and tidy. Have a close shave or trim any beard and then splash on a little of your favourite aftershave.

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