Ah, Valentine’s Day. The one day of the year where ideas of love and romantic expectations are at their peak. And many men crumble under the pressure. But, for those who’ve been hit hard by Cupid’s arrow, you’ve got a date, and the day’s schedule planned. And your Valentine’s gift sorted.

So, what are you going to wear? Well, that depends on a) the time of day and b) where you’re going to take your date. Above all, getting ready for a date is about making sure that you dress both stylishly and appropriately for whatever it is your doing.

From the cinema to the fine dining experience, we’ve selected five ways to dress for a date this Valentine’s Day, based on common date scenarios. But the rest – good conversation, manners and gentlemanly wit – is all up to you my friend.

#1 Fine DinerFine-Dining

Congratulations. You’ve managed to reserve a table for two at that expensive new restaurant she’s been begging to go to since it opened. With three-courses, moody music and copious amounts of wine, your date is bound to be impressed – if all goes to plan. So, it’s imperative you dress your best from the get go.

For the fine diner, you can’t fault a suit. With traditional dates like these, it’s far better to be dressed-up than down, but you never want to out-style your mate. Stick to a sharp cut two-piece suit with fashionable notch lapels and simple two-button closure. Grey (light or dark), navy and black are perfect dinner date colours as they are masculine and neutral, avoiding pinstripes and waist coats which tend to look too corporate.

Leaving your work shirt at home, slip a block-coloured top under the jacket – Chambray and light for a classic feel or a dark roll neck for something Euro. Either way, unnecessary appendages – ties and even belts – can be skipped. And then slide into a pair of tan leather shoes; brown a fresher take on business-y black.

#2 Lunchtime Lover


Whether it’s a cheese and wine picnic in the park or a shellfish smorgasbord on a sunlit deck, lunchtime dates – especially in summer – can literally outshine their nighttime counterparts.

Dress codes will drop down a belt notch, switching suits for separates or a modernised rendition of the blazer – the shirt jacket. Indigo is an on trend jacket finish, giving back a sophisticated denim look with the sleeves rolled. Paired with white chinos, cropped – and a black polo or revere collar shirt, this layered daytime outfit requires leather accessories: a braided cuff and brown penny loafers complementing the earthen hues of tortoiseshell sunglasses.

Reversing the look, opt for lightweight tailored chinos in dark tone and micro-print floral shirt – short or long sleeve, weather dependent. The button down should be a nice fit on the shoulder, but comfortable through the middle. Worn with white plimsols, keep the shirt untucked and add a metal ring or watch for a bit of hand bling.

#3 Movie Match


Movie dates tend to be low-key. So unless they’re an entertainment entree before a fancy meal – your look should feel relaxed but well kept.

Aim for the smarter end of the casual spectrum, starting off with a sturdy pair of cropped trousers or hemmed denim. Build with a plain cotton or plaid button-down shirt – untucked and done up to the neck, and layer an open cardigan in plush fabric over smart brogues – no socks.

Otherwise, switch formalities for sneakers and a plain cotton tee, sticking with the wider, pant-cut trouser for comfort in the theatre. Then, opt for a suede over-shirt or camo-print mac in lightweight nylon, giving back a textural ensemble – good enough to touch.

#4 Caffeine High


Even though cafes aren’t exactly michelin starred, a well-designed interior with a lively atmosphere and great-tasting coffee can be the perfect setting for a morning date (and then, who knows?) Despite it being the a.m., don’t snooze on your ability to dress well.

A smart pair of jeans, in a medium to dark wash, is your foundational item. In a slim to straight cut, select a (stainless) cotton t-shirt in a neutral hue – black, navy and taupe are chic date options being dark.

And then select your casual jacket of choice: a deconstructed blazer worn open or an active-inspired park or leather bomber jacket, both streamline with low-cut leather sneakers.

#5 On Home Turf


Home dates are the most comfortable and personal. Getting cosy on the couch or a sharing self-prepared meal in the yard, staying at home doesn’t mean the baggy sweats or gym shorts and singlets should make an appearance.

This is wear luxury loungewear and stylish active gear is necessary. Keeping the palette dark and neutral, opt for a light cashmere sweater or cotton long-sleeve t-shirt, ribbed on the cuff and hem for a more succinct fit. Khaki chinos or straight black jeans are perfect trouser choices, paired with a retro-inspired sneaker in suede, providing a good opportunity to inject some colour into the minimal outfit.

A graphic-print tee or sweater – in plush jersey – is an edgier, streetwear look. Best suited to the younger gents, pair the monochrome statement top with tapered jogger pants and minimal sneakers; nothing fluorescent or gym-related, please.

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