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Stepping into the waters of dating can be daunting at any age, but perhaps more so as a mature woman. After all, our dating lives began before the advent of social media and apps – so our early experiences of meeting people were different from what people experience today.
The number of ways in which people can meet has expanded considerably. Alongside online dating, there are work, leisure activities, mutual friends, and chance encounters.
While this makes it even more possible that your dating life can get started, it also raises questions about what to wear on a first date.
Initial impressions definitely count. What you wear can speak volumes about your personality, so, understandably, we want to set the right tone and send the right message on a first date. Most importantly, you should feel great in what you’re wearing. Confidence is the most attractive thing of all, so it’s best to wear something that helps you exude self-assurance.
Whether you’re stuck on what to wear on a first date or need fresh inspiration, check out these nine tips.
1. Be sure you know the plan for the date
Surprises are lovely, but less so when you’re not dressed suitably for the occasion. First dates can be butterfly-inducing enough, so it’s important to feel good in your outfit – not only in terms of how it looks but also how appropriate it feels.
For example, if you’re expecting a cosy pub lunch but find that a muddy woodland walk forms part of the arrangements, you may regret wearing your stylish flats.
A dinner date can raise similar issues, so settle upon a restaurant together. This way, you can be sure that you can get home easily, that the cuisine is something you enjoy, and that you’ll feel comfortable and attractively dressed in the setting.
Try to make plans a few days beforehand so you have time to try on various outfits. If you’ve figured out what to wear, you’ll be more relaxed and not racing around, tearing through your wardrobe at the last minute.
This approach also allows you time to get your items washed, ironed, or dry-cleaned before the date if needed.
2. Take food and drinks into consideration
Many first dates involve sharing a meal, which is a lovely way to get to know someone. Food is a universal language. And, eating opposite one another allows for direct eye contact, with time to look down at your plate and avoid any awkwardness.
Whether you’re nervous or not, spills can happen – and while this usually feels like something you can laugh about with a trusted friend, it can feel embarrassing on a first date.
For this reason, you might like to consider darker colours, at least on your upper half. This doesn’t need to be black, which many people find looks harsh against the skin. Why not try navy, forest green, or a pattern to help disguise any splatters?
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3. Avoid the temptation to buy a brand-new outfit
Most of us have shopped for clothes for an occasion such as a wedding, birthday, or work Christmas party. As fun as it is to buy something new, it might not be the best idea when you’re going on a first date.
The reason? This is a time to feel confident and comfortable, and sometimes that confidence and comfort are best gained from outfits you’ve worn before (and have had people compliment you on).
That said, it’s always nice to treat yourself, especially when you’re nervous, so why not splash out on just one or two things to put that extra spring in your step? It could be refreshing an existing item, such as a dazzlingly new white T-shirt from a quality brand like MUJI.
Alternatively, consider investing in a knock-out accessory, such as a stylish scarf or statement bag, to elevate your look. Osprey has a fantastic and relatively affordable range of bags to choose from.
4. Remember that classic is always a good idea
Some wardrobe staples work in almost any setting. Well-cut jeans can be worn time and again, and dressed up or down.
Paired with a crisp white-collared shirt, like this Levi’s example, or a luxurious cashmere or merino wool jumper, jeans can look elegant, particularly if you choose a stylish pair of shoes, such as ballet flats. Another idea is trainers with some kind of design detail, such as the leopard-print stripe seen on these from AND/OR.
This outfit is perfectly suited to everything from a quick coffee to a casual dinner. If you dress the look up with statement jewellery and beautifully manicured nails, you’ll be ready for just about anything.
The same goes if your date is a little less informal. If you’re headed to a fancy restaurant, a classic look will serve you well – you could trade your denim jeans for tailored black trousers and, if you’re comfortable walking in them, add a pair of heels.
A white shirt will still look elegant in this setting, but many people worry about looking like they work there. Fabric can make a big difference, so you might like to choose a top with a satiny, silky sheen, no matter the colour.
Another classic is a black dress. If you have this capsule item in your wardrobe, it’s bound to serve you well on an upmarket first date. This midi dress from Nobody’s Child is utterly timeless.
5. Embrace colour
Above, we’ve spoken primarily about black, white, and denim, but don’t be afraid to wear colour on a first date – brights can boost your mood and that of those around you. They can also help you be more confident and energised, all of which bodes well for a first date.
If you have a favourite colour, wearing it will likely make you feel good. Though if you’re unsure what colours suit you, try holding various shades up to your face to see their effect on your complexion. Do they make you look washed out or vibrant?
You can also take tests with an app such as Colorwise to get a better idea of which colours work well with your skin tone. Many consultants offer the service for a fee, too.
However, try not to be discouraged if it turns out that your favourite colour doesn’t suit you best, as you can still incorporate it into a different part of your outfit, a little further away from your face. If you like what you’re wearing, you’ll appear more relaxed and happy, which is far more important than what colour ‘rules’ decree!
For more tips, check out our article on how to dress with colour and confidence.
6. Choose comfort and style
Being comfortable is key to how you feel in almost any situation. Few things are worse than constantly adjusting a strap or pulling down a skirt.
A first date is a time when it’s doubly important that you don’t feel self-conscious, so choose your outfit according to not only the setting but also what fits your body well. It’s almost impossible to have a nice time when a tight waistband is digging into your stomach or shoes are pressing on your toes.
If you’re uncomfortable – or, even worse, in pain – it will be difficult to relax and have a good time. It may even show on your face, and your date might feel that you’re not having a good time.
The word ‘comfort’ often brings to mind baggy, oversized clothing. And while oversized looks can be chic, it’s helpful to pay attention to fabrics and choose ones that drape well, such as cashmere, linen, and silk, all of which combine quality with style.
For example, wide-legged trousers, like these ones from Marks & Spencer, fall beautifully, largely because they are pure linen. Similarly, these silk tops from John Lewis can look more elegant than some synthetic ones.
7. Highlight your best physical attributes
Let’s face it, we all have areas of our body that we’re not so keen on – but, equally, we have parts of which we’re rather fond. Advice about what to wear too often focuses on covering up, rather than showcasing, which can feel quite negative.
Is it an elegant neck and graceful shoulders? Consider a boat-neck top, like this one from Poetry, or a cold-shoulder dress, such as this lovely number from M&S. Is it a neat waist? Accentuate your shape with a belt. Shapely ankles? Try a pair of cropped trousers.
By showing off whatever it is that you like about your physical appearance, you’ll not only feel more attractive but also more confident that your date’s attention is being drawn to those attributes.
Comfort You Can Trust, Value You’ll Love
Discover Chums where everyday clothing, footwear and home essentials are designed with comfort and ease in mind.
Enjoy trusted quality, great value and a wide choice, all made to help you feel comfortable at home and out and about.
Get 20% off with code RSLS20^.
^Excludes items over £150 and those in clearance. £30 minimum spend. Valid until 30.08.26 at 23:59
8. Think about height
Above, we mentioned heel height regarding comfort, although there’s another reason you might like to consider a flat shoe or low heel. If this is a first date with someone, you might not know their height.
Of course, in a longer-term relationship, there’s no reason why women should feel awkward about wearing heels when their partner is smaller in stature. On a first date, however, it may help you both feel more at ease if height differences aren’t highlighted.
9. Harness the power of accessories
It’s perfectly normal, on a first date, to be more restrained in your outfit choices until you get a sense of what the other person is like. After all, clothing isn’t that different from storytelling – as you become more relaxed with someone, you reveal more of yourself and your past.
That hot pink jumpsuit you wore on a night out with the girls a few weeks ago might feel like too much of a statement when meeting someone for the first time. But, even so, it’s important to be yourself. Whether your usual attire is sporty, sassy, flamboyant, classic, or boho, you can use the power of accessories to indicate your clothing personality.
A croc-skin belt, for example, like this one from ME+EM, adds a touch of rock chick to a pared-back look. Alternatively, you could tie a leopard-print scarf to your handbag – this one from Marks & Spencer is the perfect size.
The same can be said for colour. If you don’t feel quite at ease in all-out colour on a first date, why not go for pink suede heels, like these from Linzi? Red statement shoes are always a great look, too – how about these low-heeled ankle boots from Lotus?
You could also elevate your look with jewellery, stacked bangles, and an eye-catching bag. There are many ways to boost your outfit’s personality without going all-out. The devil is in the details.
Final thoughts…
The idea of a first date can be nerve-wracking, but armed with an outfit that boosts your mood and increases your confidence, your chances of making a great first impression are high.
This is not only because you’ll look your best, but because feeling your best will help you to exude that feel-good glow.
Most importantly, dress to suit your own style. Your clothes say a lot about you, so don’t try to be someone you’re not – let your personality come through. Being yourself is always the best way to increase the chances of a first date going well, and that applies just as much to what you wear as to how you behave.
Have fun!
Do you have any other first-date outfit tips to share? We’d love to hear from you in the comments below.
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