What You Should Wear On a First Date

Last updated: February 13, 2022

Appearances are not everything, but when it comes to going on a date – well, let’s say that the contribution that your looks add to the first impression you make is quite important.

It is easy to spot a guy on a date who has so obviously made some wardrobe mistakes.

It’s not only your date who you will embarrass if dressed shabbily, but everyone around you will look at you and think, “He’s on a date… Wearing that?!?!”

So it’s clear that picking the right outfit for a romantic evening or daytime outing is way more important than dressing adequately for the weekdays.

So here are a few tips on how not to make any of the rookie mistakes:

If it’s a casual date during the daytime…

Taking him or her out for coffee or brunch are generally safe choices for even a first date, so you don’t have to overthink this.

Try to pick lighter colors, because they will make you look fresh and energetic.

Khakis and button-down shirts are classics – they even work great with a darker overcoat that balances the effect.

White sneakers and the right canvas will further add to the casually chic appearance.

The thing to pay great attention to is that your shoes and watch should be in any case – darker or lighter. These pieces will determine the overall tone of your appearance, so make sure they fit perfectly.

… or an afternoon beer…

For even more casual occasions that involve hitting a pub or just chilling in the city, first pick your boots and base everything else on that.

Dark washed jeans are the perfect compromise between formal and laid-back, and as usual, button-down shirts will not let you down.

Try to complement this outfit with a knit sweater or a slightly darker overcoat. It is nice to have wear stuff that if needed, can smartly transition into an adequate nighttime look.

…or even hitting the club…

Whether it’s a dinner, a dive bar, or any clubbing activities, the key here is versatility: you need an outfit that can work well wherever the night takes you.

A light oxford shirt and dark jeans will give the perfect base for the rest of your clothes.

Add a grey sweatshirt or a leather jacket, and put on some shoes that look stylish yet are easy to clean – or dancing shoes, if it’s that kind of a night –  and you are ready to be on the go.

…the main thing is confidence

(and smelling good…pick the right scent).

These are just the bare bones of what generally work in the above situations.

If you have your own set ideas for certain garments, or if the occasion requires a specific look, the above guidelines can be added to and bent to best suit your purpose.

This is because the most important thing on a date is to give out a cool, confident vibrance – you need to look good of course, but you also need to look confident and sure of your style choices and wear what you picked with ease – that will get ‘em surely.