The thought of a first date is almost always intimidating, whatever your age. However, there can be a different layer of uncertainty if much of your previous dating experience was before the rise of dating apps.
On the one hand, dating apps offer more ways than ever for people to meet and connect. But they can also make first dates more daunting if you don’t have a clear idea about who you’re meeting. So, it’s worth doing what you can to feel confident and prepared.
Wearing something you feel good in can help you appear more comfortable from the outset – which is important for making a good first impression. It can also be a fantastic way to show a bit of personality.
With that said, from outfit ideas to accessories and personal grooming, here are nine first date outfit tips for men.
1. Classic always works
If you’re unsure what to wear on a first date, a classic look is always a safe bet. You may be familiar with the idea of a capsule wardrobe, and this can be a fantastic place to start.
Capsule wardrobes are a small collection of essential, high-quality pieces that can be mixed and matched, and are suitable for various occasions. Creating a capsule wardrobe full of reliable pieces that you look and feel good in can mean you’re always set for a first date.
The other great thing about classic clothing is that it’s often suitable for just about every setting – whether a café, a pub, or a modern brasserie.
Examples of capsule wardrobe items for men include a well-cut white or chambray shirt, quality denim jeans or chinos, a casual but smart jacket, and a pure wool jumper. Shoes like leather trainers, brogues, or slip-on moccasins also have a classic, stylish appeal.
It’s worth thinking about the fabric too. Certain fabrics, such as merino wool, linen, and pure cotton are all quality, natural materials, which can make clothing look more luxurious and flattering. Retailers like Uniqlo are a great place to shop for items for a capsule wardrobe. They have a fantastic collection of polo shirts, jumpers, and jackets.
Check out our article, 10 timeless and versatile wardrobe essentials for men, for inspiration.
2. Firm up your plans before the date
When planning an outfit, it’s helpful to know what you’re dressing for. So, to avoid any last-minute panics over what to wear, it’s best to firm up your date plans in advance.
For example, are you going to the theatre? Meeting for a game of tennis? Grabbing a couple of drinks at the pub? Or, if you’re going to a restaurant, what’s the dress code?
Changeable weather can make it difficult to pin down outdoor plans so, if you’re worried about having to alter plans last-minute, it might be worth choosing an activity that isn’t weather-dependent.
3. Black makes a great base
Many of us tend to gravitate towards wearing black clothing on a first date – and for good reason. There’s an element of sophistication to black outfits, and it’s long been celebrated for its flattering qualities.
Black also provides a solid canvas on which you can build other hues and accessories. The same goes for other darker colours like navy, charcoal, and dark brown.
4. Equally, don’t be afraid to wear colour
While many people feel more confident wearing darker colours like black, brown, and navy, this isn’t the case for everybody. And there’s nothing to stop you from wearing a colourful outfit, should you wish to.
Colour is an excellent way to communicate personality and research shows that it has various effects on mood too. For example, people generally feel more upbeat and happy when exposed to it which, on a first date, is always a good thing.
If you’re after an in-between look, why not consider wearing a darker base and layer with some colour? This could mean arriving to a date wearing a non-neutral jacket or jumper that you could then remove during your get-together. This can be particularly useful if you’d rather not wear colour for the entirety of your date.
Accessories such as scarves, pocket handkerchiefs, ties, and bright socks are another great way to add a pop of colour to your outfit. For example, news anchorman Jon Snow has been recognised for combining his sober suits with colourful socks and ties.
5. Think about the fit
While it’s important to feel comfortable on a first date, it’s also worth thinking about how clothing fits. Loose or baggy clothing can risk looking scruffy or unkempt – and you don’t want your date to think you’ve not made an effort.
Equally, you don’t want to go too far the other way either and wear clothing that’s too tight. Clothes that hug or skim your body tend to flatter without constricting. Make sure you can sit comfortably and can move your arms freely.
Ideally, your sleeves shouldn’t ride up to expose too much of the wrist, and your ankles should still be mostly covered when you sit down. Think slim-fit shirts, straight-leg trousers or jeans, and tailored jackets.
6. Stick with what you know
You might be tempted to buy a new outfit for a first date, but often, it’s best to stick with what you know.
The main reason for this is comfort. You don’t want to buy a new outfit and realise halfway through a first date that you feel uncomfortable, as this could be distracting.
That said, if buying something makes an occasion feel more special and you’d like to treat yourself, it’s worth choosing something that still fits within your core ‘look.’ For example, you could upgrade an existing item by buying a new shirt or a smart new belt.
7. Personal grooming goes a long way
There’s something about a well-groomed man that communicates style and respect – so it’s a good thing to think about before a first date. Plus, research suggests that men who take care of their appearance are more likely to be confident and self-assured.
If you have facial hair, you might like to check out our articles, 6 beard care and grooming tips for men and 16 of the best beard and moustache styles to try, for tips.
Some men also use a signature scent to finish off their look. If you’re yet to find yours, why not try one of these best aftershaves and colognes for men in 2024? Other grooming tips that go a long way include keeping your nails well trimmed and your skin moisturised.
8. Accentuate your features
When planning a first date outfit, it can be helpful to focus on what you’d like to highlight rather than what you’d like to cover up. Not only can this turn a negative outlook into a positive one, but it can also make picking an outfit more fun.
For example, you could choose clothing that accentuates your hair or eye colour. This guide to wearing colours that suit you from King and Allen offers some helpful tips.
9. Don’t forget, accessories are for men too!
We tend to think more about female accessories, but there are plenty of stylish add-ons for men that can level up any outfit. This includes everything from hats, belts, and bags to gloves, rings, and braces.
One of the best things about accessories is that they can provide a subtle indication of who you are and where your interests lie, without shouting about anything. They also add a sense of intrigue by hinting at various facets of your personality that may leave your date wanting to know more.
For tips and ideas on accessories to try, check out this ultimate guide to accessories for men from Trend Him.
10. Shoes complete a look
Last but not least: shoes. As the age-old expression goes, “shoes maketh the man”, and are the key to any outfit.
Undoubtedly, wearing trainers on a first date would’ve once been frowned upon or seen as making too little effort. Now, however, a nice pair of trainers is perfectly acceptable in many situations – even stylish.
And, since they’ve become such a key fashion item, some men find it useful to set aside a pair of ‘date trainers’ that never see the inside of a gym but are reserved for those smart-casual meet-ups. Dune has a fantastic selection of stylish trainers, as does Oliver Sweeney, if you fancy a browse.
Alternatively, if you’d like to go for a more traditional look, boat shoes, brogues, or classic boots are solid options.
Final thoughts…
First dates can be nerve-wracking, no matter where you are in your dating journey. But one way to help ease the butterflies is to wear an outfit you feel comfortable and confident in. Not only can this help you make a great first impression – but it’s also a way to tell your date a little bit about who you are.
That said, regardless of the advice above, the most important thing is to present the best version of you – not an imaginary version of who you think you should be. Your personality is a bigger asset than anything that can ever be hung in a wardrobe, so try not to be afraid to let it shine through.
Do you have any other first-date outfit tips that you’d like to share? We’d love to hear from you in the comments below.