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Whether you’re in a long-term relationship or you’re single and ready to mingle, there’s no escaping the fact that Valentine’s Day is just around the corner. And with it comes the tricky problem of what to wear (or what not to wear as the case may be).

“Second to weddings, how to dress for dates is probably the most commonly asked request from my clients,” says Thread stylist Freddie Kemp. “I suspect that a lot of guys default to going too smart and can end up looking too formal for a date.”

That’s right. Unless you’re going to a really, really fancy restaurant, showing up to your Tinder date in a suit can – somewhat counterintuitively – look lazy. Why? Because it looks like you just rocked up from work and didn’t even bother to get changed. Instead, you should be aiming for an in-between sweet spot that is neither too casual nor too dressed-up, but allows you to feel confident and comfortable.

After all, they say the most attractive thing a man can wear is self-confidence.

Convey your personality

Freddie’s first piece of advice is to make sure your outfit says something about who you are, but not in a ‘look at me!’ way. Whether you realise it or not, the various decisions you make when you’re getting dressed can give little clues into your personality. Don’t believe us? There’s a whole lot of data that shows correlations between certain fashion brands and personality traits such as openness, conscientiousness, extraversion, agreeableness and neuroticism.

But putting brands aside, there’s also a lot that someone can assume about you from the types of clothes you choose. Someone who wears an oversized jumper with dropped shoulders is probably more experimental than someone wearing a v-neck navy sweater. Granted, that’s more of an extreme example, but the reason the outfit we've photographed works is because each of the product categories allows for personalisation without going too off-piste.

“You want your date to think ‘he looks great, he dresses well’,” says Freddie. That doesn’t necessarily mean that they need to be able to recall every single thing you wore. In fact, if they remember your clothes more than your chat, then you’ve done something wrong.

Take inspiration from this look and try a smart-casual jacket (be it a bomber or a Harrington), a well-fitted shirt, tailored wool trousers and leather shoes.

Boyfriend material

Have you heard the one where a guy points at his shirt and asks a potential date what material it’s made from? The answer: boyfriend material. If that was the first time you’d heard this pick-up line, then consider yourself lucky. Yet, for the purposes of this article, we’re going to concede that there might be a kernel of truth in the joke.

Obviously, there’s no fabric you can wear that will turn you into Ryan Gosling. But there are some materials that just beg to be touched. Try wearing a cosy, tactile knit on your next date and see if your companion snuggles closer.

“Texture is always effective in an outfit,” says Freddie. “It’s also easier to wear than pattern, but it gives that same effect. Basically, it makes your look feel less ‘clinical’ or ‘sharp’ and a bit more inviting.”

Another tip, try picking clothes that are more interesting in terms of cut and texture as opposed to just thinking about colour. “Too much colour can lead to you being remembered for the wrong reasons,” says Freddie. “Going for neutrals alleviates that burden, but here, the scarf adds a pop of colour and character.”

Don’t be a peacock

Freddie tells his clients to avoid ‘peacocking’. If you’re not sure what the term ‘peacocking’ means, then pat yourself on the back. That means you haven’t read The Game (a handy, misogynist’s guide to picking up women). In the book, the author tells men to wear excessive jewellery and statement hats in order to lure women closer and kickstart a conversation.

But Freddie’s advice is to stay true to your normal dress code. “Don’t betray who you are with too much bravado in the outfit,” he says. “Your clothes should complement your personality, not be a stand-in for it.”

Lastly, as Freddie points out, you never know where the evening might end up – in a bar or taking a leisurely stroll. As such, you want an outfit that has enough versatility to cover all bases.


Words: Theresa Harold
Photography: Jon Cardwell
Styling: Freddie Kemp