How To Dress For A Date

What to wear to make your date swoon

SHARE THIS ARTICLE:

Valentine’s Style

You’ve managed to secure a reservation at that superb restaurant, you’ve placed your order at their favourite florist and, after plenty of deliberation, you’ve settled on the perfect gift that shows just how much you care.

Now what the hell are you going to wear?

It’s surprisingly easy to leave this most important aspect of a Valentine’s date to the last minute, but it’s worth bearing in mind that failing to dress for the occasion after you’ve invested in everything from artisan chocolates to a surprise weekend getaway is about the same as pairing your knackered dirty Converse with your finest tuxedo – you’re simply not doing yourself justice.

But that’s not to say that you should be wearing your Sunday finest to your afternoon brunch date. It’s all about making sure that you dress both stylishly and appropriately for whatever you’ve got planned.

With this in mind, we’re giving you a rundown on what to wear to four common Valentine’s date scenarios.

The Dinner Date

Good choice; how can you go wrong with three courses of masterfully prepared aphrodisiacs accompanied by a few glasses of fine wine? Taking your date to dinner on Valentine’s Day is pretty much fail-safe – and if you’ve jumped the hurdles involved in securing a reservation, then you’ll want to match that same effort when it comes to what you wear.

It’s hard to beat a sharp suit in this instance. Given that you’ve opted for arguably the most traditional type of Valentine’s date, keep your look similarly classic by opting for a two-button, notch lapel style in light grey, charcoal, navy or black.

Remember: your aim here is to appear well-dressed and attractive, not upstage your date and make them feel uncomfortable. With this in mind, round out the look with a simple white button-down shirt or roll neck in a complementary colour, a pair of classic black Derbies/Oxfords and a neatly folded pocket square that sits firmly on the subtle, rather than showy, side of the spectrum.

If a suit is a little too much for you or the restaurant in question, then revert to a foolproof chino and blazer combo. Try a pair of slim- to straight-fit chinos in beige with a navy tweed blazer, blue Oxford shirt and pair of brown brogues or loafers. If you want to add a little formality to mark the occasion, consider introducing a plain coloured knitted tie.

Example Suit Looks

Men's Date Outfit Inspiration Lookbook - Suits and Tailoring - The Fancy Restaurant Date

Example Separates Looks

Men's Date Outfit Inspiration Lookbook - Tailored Separates - The Fancy Restaurant Date

Key Pieces

AUTOGRAPH GREY SLIM FIT SUIT

J. CREW LUDLOW SUIT JACKET IN ITALIAN COTTON PIQUE

J. Crew Ludlow Suit Jacket In Italian Cotton Pique

REISS SILVER MODERN FIT SUIT NAVY

ASOS SLIM FIT BLAZER IN TWEED

M&S COLLECTION PURE COTTON TAILORED FIT TWILL JACKET

M&s Collection Pure Cotton Tailored Fit Twill Jacket

REISS MULLER B FLECK WEAVE BLAZER NAVY

HE BY MANGO STRAIGHT-FIT COTTON CHINOS

REISS TULLUM HEAVYWEIGHT TWILL CHINOS GREY

Reiss Tullum Heavyweight Twill Chinos Grey

J.CREW 484 SLIM-FIT WASHED-COTTON TROUSERS

J.crew 484 Slim-fit Washed-cotton Trousers

REISS ASCOT BUTTON-DOWN OXFORD SHIRT SKY BLUE

Reiss Ascot Button-down Oxford Shirt Sky Blue

SELECTED COTTON ROLL NECK JUMPER

UNIQLO MEN EASY CARE BROADCLOTH LONG SLEEVE SHIRT

Uniqlo Men Easy Care Broadcloth Long Sleeve Shirt

TOPMAN HUDSON REYES BLACK LEATHER LOAFERS

Topman Hudson Reyes Black Leather Loafers

REISS CERRONI HAND-FINISHED BROGUES MID BROWN

Reiss Cerroni Hand-finished Brogues Mid Brown

HE BY MANGO LEATHER BLUCHER

The Cinema Date

We can’t give you advice on what to watch, but we’re more than happy to point you in the right direction when it comes to attire. A trip to the flicks may be a little more low-key than a dinner date, but that’s still no reason for you to slack on the style count.

You’ll want to aim for the smarter end of smart-casual for this one, just in case you end up going for drinks before or after. Start off with a solid pair of winter-weight fabric trousers such as beige moleskin chinos, indigo selvedge jeans, brown/burgundy cords or grey flannel trousers.

Build on your base with a plain cotton, plaid or chambray button-down shirt and a generously sized knit to ward off the chill – a chunky cable jumper or shawl neck cardigan would be ideal – then polish your look off with a pair of smart boots in brown/black.

We’re not promising anything but if this combination of textures doesn’t encourage your date to get tactile, then there’s little that will.