First impressionism

How you dress on the first date can dictate whether there’ll be a second.

For many women (and a few of the fellas), there is nothing sexier than catching sight of a dirty, muscled tradie or construction worker making his way home from a hard day at the al fresco office. But you can be sure as day turns to night that if he has a missus she makes him head straight for a shower and change of clothes once he walks in the door.

The same principle applies to first-date dressing. No matter how appealing something might be in fantasyland it’s a whole other kettle of fish once you’re faced with the reality. When it comes to the early stages of wining and dining, you’re expected to kick things up a notch in the clothing and grooming departments. Of course, a dazzling personality and rapier wit can be intoxicating, but prospective partners might find it hard to get past the stained T-shirt and car-washing shorts combo to discover how awesome you really are.

In the end it all boils down to respect. If you make an effort you’re showing that you’re interested in this person and want to make a good impression. Phone it in and you’re effectively saying, “Sure, you’re worth an hour of my time – a man’s gotta eat! Now, how do you feel about booty calls?”

Here are a few helpful pointers to consider when prepping for your first time.

Formal affair

If it’s a dinner date at a nice restaurant or a trip to the theatre then dress accordingly. No one is asking you to pop on a top hat and tails, you still need to be yourself – albeit the best version of yourself that you can be. Apart from your wedding day, if you’re into that scene, when else can you be expected to look your best? You don’t need to wear a suit, though no one looks bad in a well-fitted one, a blazer jacket worn over a crisp, clean shirt and dark jeans will do just nicely. You might even want to slip on a tie if the mood takes you.

Shoes are also important. If you’re booted then make sure they’re polished (use a Sharpie to cover the scuffs in a pinch), and while you’d be selling yourself short by wearing trainers to somewhere super-fancy a dark-hued – and clean! – pair are totally acceptable elsewhere. See above re: being yourself.

Keeping it casual


It’s no longer the 1950s and, as such, no one is expected to be all old-timey and dress to the nines when heading out for a casual date. Besides, meeting someone’s father straight off the bat would be awkward and somewhat creepy. But just because you’re going to the movies or for a stroll around town doesn’t mean you shouldn’t dress to impress.

Dress pants, chinos or tailored shorts are a dapper look, but jeans are also a safe bet. Even if you’re not a fan of shirts put one on. Leave the T-shirts and polos for date three. When it comes to trainers, again, make sure they’re clean. And whatever you do, don’t wear actual running shoes; they didn’t work for Jerry Seinfeld and they’re not going to work for you. Also, no leather shoes with light-coloured jeans – just no.

A nightcap

Most long-term relationships gradually slide into a gentle coma of neglected back hair and going to the bathroom with the door open, but you still have a few years before you can let yourself go if you see that as your prerogative. Granted, not all dates end with a little bedroom action, but, like a boy scout, it’s best to be prepared.

First up is underwear. As a grown man you should hopefully have figured out what brand and cut work well for you, perhaps even one that makes you look more “manly” when you’re in a relaxed state. Go with these. The only hard and fast rules in this area are: no holes and no stains.

I covered the body-hair conundrum a couple of weeks back and the only thing I’ll add is if you’re new to manscaping do it a day or two before the date. This way you can deal with any redness and address odd trimming shapes. And don’t dab any aftershave or cologne down there.

Lastly, remember to clip your toenails. Nothing quite says mood-killer like rummaging around the bathroom for a bandaid because you’ve inadvertently sliced your bed-buddy with a yellowing toenail.

Have you ever found yourself (or your date) way under or over-dressed for the occasion?