Dress to impress: what to wear on a first date

Dress to impress: what to wear on a first date

3 JULY 2018 • 11:09AM

We all know Crocs and trackie bottoms are out of the question on a first date – but which wardrobe items are guaranteed to stir up romance? We investigate…

Most people looking for love today are well versed in the art of online dating. Whether you’re a Tinder aficionado or a regular on the Telegraph Dating website, you’ll be familiar with the process: find a profile that appeals to you, strike up conversation, plan a date and cross your fingers and toes that they’re as appealing in real life.

The nerves of course, go both ways. It’s normal to worry about how you’ll come across on that crucial first meeting, and to be fearful that your date will walk away disappointed with how the evening turned out.  

Luckily, there are a few things you can do to boost your confidence before that daunting first meeting. One of the best weapons in your arsenal is to plan a fool-proof outfit that combines contemporary fashion trends with your own unique sense of style. 

And don’t worry – if you’re lacking in the fashion sense department, there’s still hope. Read on for our guide to nailing that date night look.

Make the most of your existing wardrobe

Preparing for a first date can be the perfect excuse to hit the shops and pick out some choice new items. But there’s no rule that says a first date outfit has to be completely new. In fact, there’s a lot to be said for raiding your existing wardrobe to come up with the perfect look.

Two rules to initially bear in mind when you’re planning that first date outfit are: 1) look like yourself 2) be comfortable. With these rules in mind, your existing collection of clothing is the perfect place to start.

If you aren’t sure which of your clothes look good on you, ask yourself the following questions. Which items tend to get you compliments from friends and co-workers? Which items do you wear time and again because they make you feel good when you stand in front of the mirror? And which would be the first in your suitcase if you were going on a weekend away? The items that tick these boxes are a good place to start when planning that outfit.

If your old favourites still make you feel great but are getting a little worn out you can hit the shops to find a decent replacement. But don’t forget that a lot can be achieved with a good steam iron, a smart coat and some well-chosen accessories.

Pick up some perfect new wardrobe items

Maybe you’re seeking a new skirt to go with that favourite date night top, a brand new tie that will complement your guaranteed-to-impress suit, or simply some new hair product. Whatever you’re looking for, a trip to the shops before your big date is an inevitability.

Not all of us enjoy shopping, but heading to the high street is a better option than ordering items online when you’re planning for a date. This is because visiting shops in real life lets you try items on before you buy. It’s best to go with an idea in mind but don’t be afraid to try something new and exciting – all that matters it that you feel great in it!

On a practical level, go for items that will be comfortable in a date environment. That means breathable fabrics, garments that don’t restrict your movements, and shoes that don’t need to be worn in.

If you’re still short on inspiration at this point, keep reading! We have some ideas to get those fashion juices flowing.

The perfect outfit for a day date

Day dates can be a wonderful thing, but they pose their own set of challenges. Not only are you less able to rely on Dutch courage to get you through those lulls in conversation, you’ve also got to put together a look that will impress away from the flattering low light of a bar.

The good news? Day date outfits are, by nature, more casual and comfy, which will make you feel more at ease in your skin. You’ll want to tailor the exact look depending on the activity, but suggested items include comfy shoes – so you can go for an impromptu stroll – and a smart jacket or coat (depending on the season).

For women, it’s hard to go wrong with a pair of well-fitting jeans, a blouse and a chic trench. Finish up the look with some leather loafers, subtle silvery jewellery and light natural makeup.

For men, smart jeans or khakis are also a good choice for a day date outfit. Pair with a polo shirt or checked shirt and some box-fresh trainers.

You’ll be set for pretty almost any eventuality.

The perfect outfit for for an evening date

When it comes to date night outfits it’s all about striking a balance between sex appeal and practicality. You want to look and feel your best, but not at the cost of your comfort, bank balance or ability to eat!

Though an evening date tends to be more straightforward than a day date, you should still tailor your outfit to the activity. If you’re hitting the pub for a pint before getting a curry at your favourite takeaway Indian, a suit or cocktail dress won’t be the ideal choice. An upmarket bar and chic restaurant, on the other hand, will demand a little more care and attention in the wardrobe department.

For women, a classic date dress is hard to beat. Ignore the hot fashion trends of the moment and instead focus on finding something that fits you like a glove, shows off your best features, and puts across your signature style. Pair with comfortable heels or embellished flats, a pair of statement earrings or a chunky necklace, and an appropriate outer layer. Makeup-wise, try to keep things simple and don’t attempt anything you haven’t tried before! As a note, you’ll usually want to choose between a bright lip or a bold eye – both at once can be overwhelming.

For men, it’s the toss-up between a suit or something more casual. In a more laidback setting, a white shirt with smart jeans and brogues can be the perfect look. If you’d rather go formal, wear a well-fitting suit and a smart shirt, with or without a tie. Details can come in the form of a pocket square and colour-matched belt and shoes. 

Last but not least…

Whatever you end up wearing on that important first date, just remember these rules:

  • If you’re not buying new, make sure your clothes are freshly washed and pressed. Get suits and formal dresses dry-cleaned, and take the time to properly iron shirts and blouses!
  • Polish your shoes
  • Make an effort with your hair – if it’s looking in need of TLC get a trim before your big night
  • Clean and trim your nails (and toenails)
  • Avoid those baggy grey pants and go for some undergarments that are a little easier on the eye – you never know where the night may lead you!

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