5 Fashion Tips for Men on a First Date

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Is a suit too much?

Don’t get us wrong, there’s nothing more impressive than a smartly dressed chap in a sharp suit. But in the dating world, it’s all too easy to signal that you’re trying too hard, especially if your outfit looks out of context in a casual atmosphere. Unless you’re really pushing the boat out by taking your date to a night at the opera, the tuxedo or three-piece is best left at home. Don’t worry, there’ll be plenty of occasions in the future to bring these much-loved classics out of the wardrobe. Find the happy middle ground by mixing textures and combining a fabulous statement blazer with neutral trousers, for a sophisticated — yet altogether more relaxed — alternative to a matching two-piece suit. Subtle checks and herringbone designs always work well and provide a rich contrast to plain trousers and a bright shirt.

Avoid clever clothing

‘If found, please return to the pub’. Plastered across a T-shirt, this might get a few laughs from your mates, but it sends a very clear message that at least part of you is still trapped in your student lifestyle. And immaturity is not something you want to convey during a first meeting. At this stage in the relationship, chances are you’re not entirely sure what his or her sense of humour is. Avoid second guessing or even offending your date by ditching humorous slogan clothing until you know them better. If you’re most comfortable in a T-shirt, choose a versatile polo that can be dressed up or down, depending on the setting. Pick something with bold stripes or a statement pocket to avoid your outfit verging on the wrong side of casual.

Let your personality shine through

Your first date outfit should never overpower your personality. You want your date to pay attention to you and the conversation you are making — something you’ll struggle to do if they are constantly distracted by the words on your T-shirt or your overwhelming dress sense. The same applies for eye-catching accessories like oversized watches and excessive jewellery. Don’t wear them if there’s a risk they will become the main thing that someone remembers about you. If you’re worried that your ensemble it too drab, inject some personality with a brightly coloured pair of sock. This is a subtle addition that achieves the happy middle ground between keeping things sophisticated and showcasing your sense of style.

The perfect finishing touches

Once you’ve selected the perfect outfit, the rest of your preparation is simply housekeeping. Visit the barber’s a few days before the date to neaten things up and indulge in a luxurious Turkish shave. It’s also an idea to treat yourself to a new aftershave; little touches like this will fill you with confidence and anticipation for what could be the exciting new beginning of a relationship. Nobody likes to be overwhelmed by powerful aftershave, which is why you should opt for something subtle, spicy and sensual. Like an overpowering piece of clothing, a strong scent will eclipse the impression you make, so subtlety and light application is key.

Put on your dancing shoes

As the saying goes, you only get one chance to make a first impression. Your shoes can say a lot about you, so opt for clean and stylish footwear for your first date. We say relaxed brown leather boots for an afternoon museum visit or a stroll along the coast, and polished black brogues for an evening dinner or a show. Trainers and flip-flops? Generally a no-go area, unless you’re doing something highly active for your first encounter — and that doesn’t mean a salsa class!


We know that finding a meaningful relationship isn’t all about looks. But when you’re embarking on a first meeting with someone, appearances make a massive contribution to that all-important first impression.

With that in mind, we’ve asked the experts at British men’s fashion label Guide London to offer their advice on the crucial first date outfit. These five handy tips are by no means steadfast rules and might not work for everyone — after all, your outfit should showcase your personality. But if you’re deliberating whether your comfy trainers are suitable or it’s really a good idea to wear that slogan T-shirt that always gets a laugh down the pub, we’re here to guide you along the way.


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