Dating. It’s a minefield. If you’re not getting flack for buying her the same shoes her BFF already has, she’s laying into you for choosing a restaurant where the music’s too loud. Or the lighting’s too low. Or where they don’t take substitutions so she has to break the raw diet she’s been sticking to religiously and it’s all because of YOU – you lazy, inconsiderate, good-for-nothing…

But take heart. Because we’re arming you with the insight to make any date memorable – whether you’re on your first or celebrating your 25-year anniversary. These are, according to some of menswear’s most formidable women, the rules to getting it right.

Relax (Your Threads)

“I like a man to be clean, but preferably not too fragranced – and he should look as if he has good taste, but in an effortless way,” says Jane Shepherdson, Chief Executive of Whistles. “He should never be overdressed; in fact a shirt and jeans (nothing too shiny or glittery, mind) are usually fine.”

Nadyia Dunston, Senior Stylist at River Island Style Studio Oxford St. – and a woman who spends a good deal of her time steering men towards sartorial success on dates – agrees: “Keep it simple. Girls love a man that has made the effort, but a suit might be a little over the top for a date. Mix it up with some well-fitted tailored separates – slim trousers, a roll neck jumper or Oxford shirt and a sharp blazer is a fail-safe look when combined with a classic brogue or Derby shoe.”

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Relax, But Still Give A F**k

“The current trend among many men seems to be stuck deep in streetwear basics, which is perfectly acceptable when it’s done right. But there’s a thin margin of error between a casual sweatshirt-and-sweatpants combo and looking like you really don’t give a hoot,” says Ana Kinsella, Editor at Bon magazine and freelance fashion journalist. “Good fit and attention to detail are key here in walking that fine line.”

“If you’re a streetwear guy – be a streetwear guy,” says Dunston. “Just go for an ‘upgraded’ version of your day-to-day look; so instead of wearing a longline T-shirt and bomber jacket with your trainers, try a cropped smart trouser and button-down Oxford shirt.”

river island Selected Homme Jeans 2014 Gant Rugger AW14 asos

Confidence Is Key

“If you try to wear something that you’re not comfortable in, it will show,” says Dunston. “And one thing that’s more attractive than any item of clothing is confidence.”

But Nobody Likes A Show-Off

“While it can be tempting to disclose any recent successes in dating, remember that nobody likes a show-off – and the same rule applies to your wristwear,” says Muhaddisa Fazal, Fine Watch Buyer at The Watch Gallery.

“Massive showpieces with overt branding and an abundance of diamonds may earn kudos from a Mayfair bouncer, but you’ll get little from a discerning date. Keep things simple and geared towards the classic – you can still channel a prestige brand without peacocking.”


Stop Copying Footballers’ Haircuts

“If your only frame of reference for looking good is whichever footballer is most zeitgeisty right now, please consider getting a second hobby,” suggests Kinsella. “I think some men think copying an athlete’s thing is an easy way to look cool, but to me it implies that he’s trying too hard to look current, which can seem pretty sad in the long run.”

Instead, play it safe by sticking to a cut that suits you and pay your barber a visit ideally the day before the big night to ensure your barnet’s on point.

It’s All In The Fit

“Wear well-fitting clothing,” says Elena Renaudiere of online men’s personal shopping service “A few inches here and a couple of inches there can make a huge difference to both your overall appearance and the way you feel during your date.”

You know the drill, if it doesn’t already sit right, then take it up with your tailor to ensure a glove fit.

Scentual Healing

“The way to a girl’s heart is through her nose,” says Amber Siegel of design duo Baartmans & Siegel. “The way you smell can be even more hypnotic than your touch or appearance. If Play-Doh created a fragrance, for example, I’d be hooked – that warm almond smell is heaven!”

Siegel suggests finding a signature scent that taps into your date’s olfactory tastes. “Look for perfumeries that create bespoke fragrances,” she says. Visit Jermyn St.-based perfumers Floris for a bespoke service that lets you bottle exactly what you’re about, or try layering the existing contents of your bathroom cabinet to create a scent that’s more than the sum of its parts.

Shoes Maketh The Man

“Make sure you have a fitting pair of shoes for the occasion and, most importantly, make sure they’re in good nick,” says Dunston. “There’s nothing worse than your significant other turning up looking HOT from the ankles up, only to let themselves down by donning a pair of scuffed up old brogues that are doing that weird ‘duck mouth’ thing at the front.”

It’s all in the (pristine) presentation: “If you’re wearing a hard shoe, it should be clean, freshly polished and in good condition. It doesn’t have to be a formal style, mind. If you are wearing trainers though, they must be clean.”

…But The Logos Do Not

“Ultimately, a man should recognise which items suit him and which don’t,” says Renaudiere. “And it has nothing to do with a logo on your clothes, but the way you feel wearing them instead. A well-dressed man respects brands for their quality and fit, but won’t buy something purely for the sake of a name.”

As For The Date Itself?

Arrive Early, Not On Time

“Arrive five minutes early,” says Lauren Luxenberg, Social Media Content and Community Manager at

“Women will more than likely arrive five minutes late, but it shows you’re chivalrous if you’re already there to greet your date and you’ve chosen a spot to sit at.”

Experience Is Everything

“For me, it’s less about expense, more about the experience,” says Dunston. “It’s not about pouring money into a date at a fancy place, but how unique the date is as an experience.”

“Do your research, take an interest in what she likes and plan something around that. Make memories. Apps like Dojo help you find cool places that might be date-worthy – from rooftop cocktail bars to street food stalls to boutique restaurants.”

Step Away From The Smartphone

“One of the most important things on date night is to show that your attention is devoted to the person you’re dating,” says Luxenberg. “The worst thing you can do is constantly check your phone. Just put it in your pocket, and forget about it.”