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What To Wear On A First Date: Style Advice For Every Occasion

02 December 2025 4:20pm GMT

So you’ve organised the date and time, agreed on the location and now all that’s left to think about is what to wear. But deciding on a first date outfit can be daunting. Whether you’re a fashion obsessive or have little to no interest in clothes, everyone wants to make a good impression. But how do you do that while feeling comfortable and showing up as your authentic self?

Before you go out and buy a brand new outfit, we asked personal stylist, Helen Thomson for her top tips on choosing the perfect first-date outfit. Read on to find out more about how you can show up for your date looking and feeling your very best.

The importance of first impressions

“If you’re meeting someone for the first time, it’s important that what you wear makes you feel good and reflects your personality,” says Ms Thomson. “Whether you’re outgoing or more reserved, you can use colour, style, and pattern to give your date an insight into your life before you’ve even said ‘hello’”.

Ms Thomson adds that first impressions really do count. “The average person makes up their mind in just seven seconds about whether they like someone or not,” she says. So, while you should feel comfortable, be brave and wear something you love and feel great in on a first date.

Tips for choosing a first date outfit

1. Consider the location

“Choosing an outfit for a date is all about planning. Look up the location before you go and always check the weather for footwear options,” says Ms Thomson. “If the venue has a social media page, it’s a good idea to see what other guests have worn there before to get a sense of the mood”. Likewise, if you’re going on a more active date, don’t wear a new pair of trainers that might rub and ruin the experience for you. It’s also wise to dress in light layers so you’re prepared for all eventualities and changes in weather. This is especially important if the date is outdoors like a walk or picnic date.

Discover more tips on what to wear on a walking date

2. Pick something comfortable

When you feel uncomfortable in an outfit, it can be really distracting and also make you feel self-conscious. You can avoid this by putting on your outfit a day or so before and wearing it around the house.

Are there any gaping buttons?
Is the neckline too low and causing you to keep pulling it up?
Do you feel comfortable sitting down or is the waistband digging in?
Can you walk comfortably in your shoes?

If the outfit passes all of these tests, then you can feel calm and confident that it’ll work on the day. “You want to feel comfortable, but also the best version of yourself - it’s a fine balance,” says Ms Thomson. “If you feel good, you’ll naturally be more relaxed and happier on the date”.

3. Be yourself

“When choosing your outfit, go for something that feels special and true to you, but also suits the occasion and location,” says Ms Thomson. A walking coffee date, for instance, will require a much more casual outfit than one for an evening at the theatre or in a nice restaurant.

What’s more, while it can be tempting to try and rebrand yourself on a new date by wearing something you wouldn’t normally, if it’s not authentic to who you really are, it may stop you from forming a genuine connection with someone new. Remember, the person meant for you will accept you for who you are, not a version you think they’ll like.

First date outfit ideas

Stuck for first-date ideas? Try Ms Thomson’s expert-approved outfit suggestions that will help you feel great and exude confidence.

“For women, a fabulous dress or co-ord is a great choice for a first date, paired with flat or low-heeled sandals to keep the look stylish and effortless,” advises Ms Thomson. She adds that slip dresses that skim the body, drop-waist midi dresses, or silky top and trouser sets can also make great options for a first date. What not to wear? “I’d avoid towering stilettos on a first date and instead embrace the comfort and confidence of a flat or low heel,” she says. “Dress up your outfit with jewellery and add a statement bag to show some personality”.

What to wear on a first date for men

“For men, a relaxed shirt in a print, stripe or colour works well with tailored trousers and a loafer or stylish trainer,” suggests Ms Thomson. “For a more formal setting, a light blazer and contrasting trousers looks smart and refined when paired with a light shirt or crisp white T-shirt, depending on the dress code”. She adds that your look should feel understated and inherently stylish, while still expressing your personal style. If your look is more active, you can keep things a lot more casual with leisurewear or gym gear. Just don’t forget the smaller details like making sure your shoes are clean and that you smell great upon arrival. (Veer more for smelling fresh rather than wearing heavy cologne or perfume).

Still feeling indecisive about your first date outfit?

If you still feel unsure, consider making yourself a personal styling appointment at a department store or in your favourite retailer. A stylist can then help you choose a few capsule pieces that you can build great looks around. Having a second opinion should also take much of the guesswork out of what to wear on a first date and make you feel more confident.

How to embrace self-confidence

If you’re newly divorced or are embracing a new chapter in your life after the loss of a partner, finding your self confidence again can be tricky. Ms Thomson says that finding the right outfit, however, can have an amazing impact on your self esteem and help you show up confidently to a first date.

“The key to confidence on a first date is feeling happy in who you are and how you present yourself,” she says. “It’s amazing how transformative wearing the right colour or style can be and how it can change the way we feel about ourselves, and in turn, how others see us”. She adds that if you arrive at a date wearing an outfit that makes you feel uplifted and self-assured, you’ll naturally radiate confidence and positivity. “We all get those butterflies when we first arrive and may feel a bit nervous but put your best foot forward and remember to enjoy the experience”.

Whether you’re heading to a restaurant for an elegant lunch date, or choosing a date idea that’s something a little different like kayaking or dancing, make sure you feel comfortable and confident in the outfit you choose. The rest will fall into place and leave you free to get to know that someone special a little better.

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