The Gentleman’s Guide To Dressing Up For The Big Date

The Gentleman’s Guide To Dressing Up For The Big Date

Can I wear sandals for brunch? What if I wear a vest at the tiki bar? Will a two-piece suit look too much for a movie? What if I don’t find matching socks and I am already late? Should I go commando? Should I not go at all?

Sartorial choices can always be stressful, even more so when you want to make that great first impression that you hear about in dog-earned romance novels. Want to shine bright (without wearing a sequined jacket) on your fabulous first date?

Brunch, a quick movie, drinks or dinner, don’t stress — here’s how you dress:

1. Late night movie

The movie might be critically acclaimed, but that doesn’t mean your outfit should be too. Keep it casual – a Henley and jeans – and you won’t be surprised to find more than one happy ending when the curtains close.

If you feel a little bare, it’s probably a good idea to carry a jacket along – that way, if you get drinks after; you have something to hold your seat with (side note: not unless you are holding on to your date).

 2. After-work drinks

Change out of your suit, unless you want to look like you are attending a sales convention in a city far away from home (and your wardrobe). Instead, wear a dress shirt with fitted jeans, and you’ll find your way into your very own Hallmark movie – that way, the cocktails (happy hours, if you want to make the most of it) won’t be the highlight of the night anymore.

Going straight from work? Trade in your blazer for a casual dinner jacket or a sports coat – one that says ‘Hey, I made the effort of going home and changing for you. That counts, doesn’t it? Do you want to buy me my first drink?’

If nothing else works, go all black. Black can never go wrong (although Donald Trump would not agree).

3. A casual dinner

Is it dinnertime already?

Skip t-shirts with a message (yes, even your Homer Simpson tee) and go classic with jeans and a collared polo that’s not too loose (or at least, less loose than you were in your raging single days) – that lessens your chances of looking straight out of an Ed Hardy catalogue. Go casual, go clean, and go crisp.

PS: if you avoid the fedora, there’s a high chance you’d be a part of the doggy bag that goes back home.

4. Sunday brunch

Sunday brunch is the king of great first dates — unlimited alcohol, breakfast items and the only plausible excuse to wear sunglasses when you are out with someone you are romantically interested in. All in all, it’s the bumper prize at the end of a horrible week (or life).

Stressed about what to wear when you should instead be stressing about how many glasses of champagne you can down without leaving a bad impression? It’s simple. Opt for a well-fitting polo shirt or a button down with khakis, and you are good to share Bellinis and brioche on toast with your future plus one.

Wear shorts only if your brunch is at your friend’s backyard barbecue. In which case, there won’t be a second date, so you should probably stock up on those hot dogs while you can.

— Illustration courtesy Amrai Dua

Aniruddha Mahale