The Gentleman’s Guide To Dressing Up For The Big Date: Take Two

The Gentleman’s Guide To Dressing Up For The Big Date: Take Two

Still stressed about dressing up for the big date?

From a fancy romantic meal to a casual walk in the park, this no-fail blueprint will have you looking sharp and earning brownie points by the dozen. So, pay attention.

A fancy, romantic meal

The odds that you go to a fancy romantic meal on the first date might be next to nil (considering it ricochets your relationship from zero to ‘How did we get here so fast?’ in 20 seconds) but if you do, go easy on your style just like you would go easy on your wallet.

Keeping it simple is as important as knowing that you should never bring up the ex. Wear a dinner jacket with a button down and let a pocket square be the feather in the cap (Side note: there shouldn’t be any caps. Or feathers). You don’t want to look like you’re a ridiculously expensive entrée being served on a plate. Keep the garnishing to a bare minimum. Avoid jewelry – unless you are on a date with your partner of five years and two dogs, and wearing a wedding ring.

At the end of the day, you are eating a fancy meal; you don’t want to look like one.

A walk in the park

Contrary to popular belief, outdoorsy dates aren’t the sartorial wet dreams that movies make them out to be. See, you can’t show up for a hike in haute couture – because mud stains will never look good on your Italian Moschinos. Wear clothes that you can sweat in (but don’t show up in sweatpants) and stick to colours that are light (just like your conversations).

Just make sure you wear a really good pair of sneakers so that you can sprint away should things get awkward (and there’s a high chance they will. What kind of weirdo suggests going on a walking date? Oops, sorry. That would be me.)

Coffee shop

Three words: keep it casual – just like your cup of coffee (unless you are one of those horrid souls whose coffee orders are more complicated than the Advanced Physics final I took in college).

The art gallery

Like fancy restaurants, art gallery dates can be tricky – you want to look like a piece of work, but you don’t want to look like a piece of work that’s being displayed at the art gallery.

A great way to add to your savvy is to dress savvy with a casual two-button blazer—one without gaudy lapels—with a clean oxford underneath. Leave the bowtie at home, with your boring ideas on post-modern surrealism. A clean pair of suede or premium leather bucks would set this fit to menswear aficionado, which, by proxy, is a prerequisite of art appreciation. And even though you won't have a good answer for your take on whether or not minimalist art is an oxymoron, you can still look like you know what you're talking about.

Just like I do.

Essentials for every date:

Clean underwear

If the date goes well and you get lucky, you don’t want to be caught naked wearing greying (or worse, stained) underpants. Even though that’s a paradox, always wear underwear with the assumption that you are going to take a chiseled underwear model back home.

An undershirt

Nervous sweats aren’t sexy – you don’t want to be exchanging sweet nothings with your date when all he can think of are the giant pit stains under your arms. Invest in an undershirt, so that your flirting doesn’t get underplayed. Keep it white; keep it simple.

A white shirt

The white shirt is the golden ticket – it’s so versatile, it could be Meryl Streep. Pair it with khakis, pair it with jeans, pair it with a leather jacket, pair it with beach shorts if you want to – you’ve got a winner every single time. Now about your comic timing…


Have a signature scent, and dab just enough to sign off all your dates with. It’s a signature and not a full-fledged novel, so don’t overdo it.


Manners don’t make a great man, good shoes do.

Dates trust men with unpolished shoes much less than men without wallets. Always have five pairs of shoes with you – black dress shoes, brown dress shoes, a pair of brogues, one set of canvas sneakers and cute moccasins that you can fall in love with, the one off-chance you never find anyone else.

A watch

Unless you are a school student who can’t tell the time, there’s no other reason why you shouldn’t be wearing a watch on your date.

Read part one of The Gentleman’s Guide To Dressing Up For The Big Date here.

— Illustration courtesy Amrai Dua

Aniruddha Mahale