What To Wear On A First Date For Men

By Rebecca Cox

3 years ago

The most important thing is to be yourself. (But the best dressed version.)

For better or worse, first impressions count for a lot in dating. You may eventually win someone over with your witty conversation or charming smile, but will you be given the opportunity if the first impression is bad? Because dressing for first dates is notoriously challenging, we’ve partnered up with Church’s Footwear, maker of first-date-worthy shoes, to bring you a guide on what to wear on your next date.

What To Wear On A First Date, For Men

Of course, what you wear will need to be occasion appropriate. If you’re going to the pub, don’t turn up in a suit, or if you’re out for dinner, flip-flops are a no-no (clue: flip-flops are always a no-no on a first date, unless you’re going to the beach, and even then, a sandal would be better). But there are several rules you should stick to when it comes to ensuring your outfit won’t be the reason there isn’t a second date.

The Right Shoes For A First Date

Let’s start with shoes. Believe us, your date will be judging your footwear. Yes, they may be willing to overlook a bad haircut, a poorly advised hat, even a badly-fitting jean, but turn up in over-shiny, tight loafers with no socks and a few inches of ankle on show and (most) will struggle to move forwards. If you’re out for dinner, a classic brogue will do nicely, if it’s a more casual affair, some stylish sneakers are called for. Pick the right socks, not novelty, not brightly coloured, but please, please, wear socks.

Logo No-Go

Avoid big slogan or bold logo tees, jackets or accessories. Dress simply but smartly in clothes that whisper understated, timeless elegance rather than scream ‘shopping problem’. And it should go without saying but there shouldn’t be a cartoon character in sight, from t-shirts to socks.

Be Versatile

If you’re not sure how dressed up or down your date is going to be, opt for a casual outfit with a smarter jacket or trench that can dress it up, or a slacks and shirt outfit that you can make casual with an army or denim jacket.


While you want to look like you’ve made an effort for your date, being too ‘done’ can be off-putting. Simple, neutral separates will look like they’ve been chosen carefully then combined carelessly with a natural, easy stylishness.

Ready to elevate your first date wardrobe (which will, hopefully become your second, third, fourth date wardrobe)? Shop our picks, below.

First Date Outfit Ideas For Men

Churchs Chetwynd Superior Calf Leather Oxford Brogue in Burgundy

For more tips, check out our guide to outfit finishing touches