What To Wear On a First Date

What to wear on the first date is always a conundrum. You want to look effortless yet smart, sexy but not too available. But most importantly, you want to dress true to yourself. Because no matter how much someone might claim they never judge a book by its cover, we all do. Within the first seconds of seeing someone, we make a snap judgement based on what they are wearing, and whilst perceptions can change, it’s much easier if you’ve already portrayed the image that’s right for you. 

1. Be comfortable 


No that doesn’t mean going out wearing jogging bottoms and trainers. It’s simply about wearing something that makes you feel good about yourself. It might be a personal favourite item of clothing, or something you’ve received lots of compliments on before. Confidence is the key to style, so if you are wearing something that you feel uncomfortable in – no matter how fabulous it is – it will come across. So wear a failsafe outfit to let your inner confidence shine through. 

2. Jeans are acceptable 


Once upon a time, jeans were strictly casual attire. But with so many styles now out there, a beautifully cut pair that flatters your figure can look just as smart as tailored trousers (particularly if you choose a dark, slim-fitting pair). Jeans are ideal for nailing the ever confusing ‘smart casual’ look as they provide the perfect blank canvas to build your look around. Just add a gorgeous blouse and beautiful heels, and finish with a few statement accessories, and you’ll look both stylish yet effortlessly cool. 

3. Put the past behind you 


Heard of ‘lucky pants’? Well as mythical as it might sound, studies have shown that wearing something you have an emotional connection to can have a big psychological impact. So in the same way you should wear something that makes you feel good, avoid anything that has any negative history attached to it. It may be stunning, but you want to be focusing on the date, not recalling a bad memory every time you notice it. So steer clear of anything that might unnerve you, or could invite comment by your date (such as a piece of jewellery) so that you can remain relaxed and happy. 

4. Consider colour 


Many 50+ women gravitate towards navy, grey or black because it makes them feel ‘safe’. But you want to be showing off the best version of yourself on the date, not the safe version. So if this sounds like you, try giving colour a go. The thought of wearing colour might sound a little scary at first, but the outcome will be worth it because you’ll feel stronger and more confident. 


Need convincing? During a study on the psychology of wearing colour, a series of photos of different people were shown to a group, and the majority found those wearing red to be more attractive. They then showed the same photos in black and white to another group; the result was the same. But it wasn’t because people generally prefer red. It was because the colour had made the wearer feel more confident, which shone through in the photograph, making them more appealing. 


That doesn’t mean you should always wear red – it simply proves that wearing colour, in particular one you really love, can make a world of difference to your confidence. 

5. Show off the parts of your body you love


There can be a worry about looking like ‘mutton dressed as lamb’ if you show off too much skin, or wear something that is super clingy. But if you get the balance right by just focusing on one of your best ‘assets’ — such as your shoulders, arms or legs – you can still show skin whilst looking sophisticated. 


The key is to avoid showing off too much skin altogether – if you’re showing more on top, wear trousers or a long skirt on the bottom; or if you’re going to show off your legs, wear a more demure neckline. And if you’re wearing something tight, even less skin exposure is needed – and can actually be very alluring. That way you can keep it classy, whilst also feeling good about yourself. 

Jacynth Bassett is the founder of the-Bias-Cut.com — the first pro-age online premium fashion boutique, where ageism is never in style. Swiftly becoming recognised as one of the UK's leading pioneers of style at every age, Jacynth has written on the topic for several leading national publications, and is the monthly style columnist for several 50+ online platforms. She is also often invited to speak on panels, podcasts and radio, and has contributed a chapter on grown up style for an internationally published book.


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