The Men’s Guide: What To Wear On A Date

By Shane C. Kurup

9 hours ago

Fretting about what to wear for your big date? Take some style cues from our cheat sheet guide and dress to impress


Ever since we first swaddled ourselves in animal skins, mankind has obsessed about dressing for the occasion – and there are certain occasions where making the right impression with what you wear can be a make or break affair. As if the assault course of modern dating wasn’t enough of a minefield, deciding what to wear for your romantic rendezvous can cause you to break a sweat before you’ve even put your card down for the reservation. You want to dress to impress, but not like you’re trying too hard. Shane C. Kurup shares some sartorial inspiration to strike the right balance, wherever your date takes you.

The Men’s Date Style Guide


The Pub Lunch Date

The rustic setting of a country pub doesn’t tend to lend itself well to starchy collars and cufflinks, so a rugged yet refined look is a better fit for the backdrop. Instead of the ubiquitous waxed jacket, score some extra style kudos with a slick leather iteration and pair it with some well-cut velvety cords, which will also be useful for disguising any stray spots of gravy that might land in your lap. A pair of sturdy, tread-sole Derbies will keep you grounded if you decide to take a post-lunch stroll across the village green to digest all that hearty grub and if there’s a roaring fire going, a rich, woody scent will play on the smokiness as you sip a dram or two by the hearth.

READ MORE: Where To Get The Best Roast Dinner In London

Tweed cap | men first date style

Purdey

Small Check Baseball Cap in Clay, £225

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Leather jacket | men first date style

Zegna

Padded Full-Grain Leather Field Jacket, £9,350

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Check shirt | men first date style

COS

Checked Pima Cotton Shirt, £85

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corduroy trousers | men first date style

Oliver Spencer

Orsman Trousers Deakin Cord Grey, £210

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Watch | men first date style

Seiko

King Seiko ‘Forest Green’ 6L 1969 Re-Interpretation, £2,750

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Fragrance | men first date style

Lalique

Encre Noire Eau de Toilette, £79

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Brown shoe

Crockett & Jones

Denver Dark Brown Rough-Out Suede, £520

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The Dinner Date

A dinner at a highbrow establishment in town calls for a bit of spit and polish, so leave the sweats at home (even if they are cashmere) and slip into something a little more tailored. A strong-shouldered velvet jacket will not only make you stand out for all the right reasons, but the plush, texture-rich fabric will leave your date with a warm, fuzzy feeling if they happen to brush your arm. Level out the tailored fit of your jacket with a pair of wide-leg trousers that will give you room to breathe when you hit the third course. While the jury is out on whether sneakers are acceptable at a swanky restaurant, a pair of monkstrap loafers strike the perfect balance between off-the-clock and refined – and won’t offend either your date or the maître d’.

READ MORE: The Most Romantic Restaurants In London

Velvet blazer

Thom Sweeney

Velvet Single Breasted Peak Lapel Dinner Jacket, £1,995

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Striped tie

Turnbull & Asser

Navy Broken Shadow Stripe Silk Tie, £205

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Black trousers

Girogio Armani

ASV Cupro Basketweave Single-Pleat Trousers, £1,100

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Watch

Piaget

Andy Warhol Watch, £49,600

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Silver signet ring

Dunhill

Signet Armorial Silver Ring, £495

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Black loafer

Edward Green

Horton, £,1250

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The Active Date

If your romantic interest prefers to get physical on a date (easy tiger), then you’ll need to dress for the activity at hand. Perhaps it’s a brisk hike over a tor, a rock-climbing session or a round at the archery range. Chances are, you’re probably going to end up outdoors, which comes with its own set of hazards – the fickle British weather, for one. So make sure you come prepped with a decent waterproof and sturdy clodhoppers to tackle any sudden downpours or slippery terrain. You’ll also want a watch built for rugged pursuits, so you can make it to the pub in good time before the kitchen closes. And while a compass might seem archaic, not only will it lend you a touch of nerdy allure, but you’ll be able to impress your date with your orienteering skills should you get lost – and not just come off as a Gorpcore poser.

READ MORE: Lovely Walking Routes That End At Cute Country Pubs

Green jacket

ThruDark

Vanguard Jacket, £350

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Watch with green strap

Breitling

Super Avenger B01 Chronograph 46 Night Mission, £8,050

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Black shorts

Dubarry

Imperia Mens Technical Shorts, £129

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Pocket compass

Dalvey

Pocket Compass, £284

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Walking boots

Moncler

Peak Rubber-Trimmed Leather Hiking Boots, £780

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Black backpack

Montblanc

M-Lock Backpack, £ 1,500

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