Impressing your online date with your fashion choices

Look, we’ve all been there; even though some of us will vehemently deny it. I’m talking about trying to impress someone, a date specifically. It used to be a tricky thing, especially if it’s someone you’ve just met in a club or a café. A good first impression can literally make or break your future chances; if you do badly, you won’t get an opportunity to make a second one.

Fortunately, this has become easier in the era of online and phone dating. Whether you’re using a website, an app or a chat line service. So, in order to save you from another lonely night, here are some tips on what to wear (and how to figure it out) when you’re meeting someone you’ve met online for the first time.

Do the research

You’ve been talking to that person for some time, presumably (well, you’ve at the very least exchanged a few texts and you’ve seen their picture). So, you should have at least a vague idea of what they like. You may even know their name, in which case you can do some cyberstalking and find out more. Just be subtle about it, no one likes being snooped upon.

There you have your starting point. If you’re a chameleon you can just dress un in the way most likely to elicit a positive reaction. If you actually want to stay true to yourself, then just modify your style a little bit in the way your date would appreciate. If you don’t want to change anything about yourself… why are you even reading this?

Without further ado, here are some tips for your first date that you should pay attention to.

Be casual, but not too much

There are few people who go super formal or stylish for a first date, so keep it casual. The only thing you have to worry about is the degree of casualness. Keep in mind though, going casual doesn’t give you a license to be a complete slob; put at least some effort into it.

You can’t really go wrong with a nicely-fitting, button up shirt. Get a solid color and pair it up with a pair of loose khaki pants. Alternatively, you can just grab a stylish polo shirt and a nice pair of jeans. Both of these options are relaxed but show you have at least an ounce of fashion sense.

Glam up

There is a chance your prospective date will like something a tad fancier. If that’s the case get yourself a nice blazer over a button up shirt and you’re good to go. Well, note entirely; make sure your blazer fits you properly. Clothing should embrace you just gently enough. If it’s too tight or loose, just pick something else, you don’t want to be suffocated or look like you’re wearing a sack.

If you expect to go to a nice fancy restaurant, you’ll need to kick it up a notch. A suit is a perfect choice; you can’t really go wrong with navy for that suave and stylish look, you can even skip the tie. Same as with the blazer, make sure your suit fits right.


No outfit would be complete without a nice pair of shoes. Be careful here, though. And make sure you have figured out your date’s preferences. People into the alternative scene prefer sneakers and the relaxed footwear. However, if you think they might prefer a more chic look, opt for a nice casual pair of leather shoes instead.

Of course, your belt should match your shoes; the devil is in the details, so make sure the Old Scratch is on your side.

There you are, some basic guidelines on how to dress up for a date you’ve arranged online. Just make sure to follow them and use your common sense. You can thank me later.

Cole Matheson

Cole Matheson is a professional writer and fashion enthusiast. He writes for various fashion and lifestyle blogs and is always ready to give a helping hand to the sartorially challenged.

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