H’s guide to first-date prep

H’s guide to first-date prep

First date

You’re gearing up to take out <<insert potential love interest’s name here>> for the first time. Make a better first impression – and give her something nice to look at – with my tips for what to wear on a first date.


This isn’t rocket science, mate. Women like men who have gone to some effort – taken some time – to look nice. A neat, smart appearance shows her a degree of respect and that you care about the impression you’re making on her.

A nice outfit can work to your advantage in other ways, too. Take it from the old song: You’ve got to accentuate the positive and eliminate (or at least cover up) the negative; clothes are a great way to emphasise your best features (strong biceps, broad shoulders) and hide your flaws (that slowly encroaching beer gut).

Investigate the sartorial situation

But before you know what to wear, you need to know where you’re going. In my experience, most initial get-togethers are coffee meetups or dinner dates. If you’re taking her to dinner, do both of you a favour and check the restaurant’s dress code. (And be sure to let her know what you find out.) For a nice casual restaurant with good ambience, I recommend a goldilocks approach: not too overdressed, not too underdressed … just right.

Don’t sweat it

No matter how much predate research you do, you’re still bound to be a bit anxious the night of the date. And often when men are nervous, we sweat. But don’t fret the sweat. Instead, double-up on the deodorant and wear a white button-down shirt, which won’t show the perspiration the way blue or other coloured dress shirts can. And be sure to invest in a new one, as white shirts that have been around a while can look tired and dirty. A fresh one is clean, crisp, and smart-looking. Plus, it matches everything.

Remember: you’ll start to feel more confident if you look confident.

The comfort factor

In the past, I’ve said that a first date calls for new shoes. I’d like to slightly amend my advice: You want nice, clean shoes, but new footwear is often be stiff and uncomfortable. There’s enough discomfort on a first date without your feet hurting, too. If you do buy a new pair of shoes, make sure you break them in for a week or so before the date, or the blisters may be what you remember from the evening – not the stimulating conversation or the unexpected goodnight kiss.

Also, if you opt for brown shoes or boots, wear a matching brown belt. Likewise, black shoes or boots, black belt.

Factor in comfort for your choice of trousers as well, or, dress-code-permitting, wear a dark, slim-fit pair of jeans.

Take it up a notch

Though I wouldn’t recommend a suit on a first date (see goldilocks reference above), a trendy sports jacket can be a nice touch. For one thing, sports coats are very flattering on most men (remember the accentuate-the-positive point, also above?). Plus, if the night gets chilly, you can give your jacket to your date – major brownie points!

Whatever the outfit of choice, be sure to try it on before you go on the date. That way, you can make any necessary tweaks. (This is when the well-dressed man’s essential helpers can come in handy.)

As for accessories

Keep your accessorising to a minimum. A nice watch is often all you need. A female friend of mine says she loves men’s watches – they draw attention to men’s hands (something she also loves), and there’s just something masculine and strong about them. Also, because watches are usually very personal items, they often give just a little hint of your personality and style.

Finally, I always recommend that men carry a hanky … for those just-in-case moments.

Do you have any first-date tips you’d like to share? Comment here or on our Facebook page.

Cheers for reading. H

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