Text Less.

Join us in discovering an exciting
and visual way to date

First Date Fashion

  • by

You’re about to go on the first date with your Chekmate match, but before you can decide how to break the ice or introduce yourself, you need to figure out what you’re going to wear.

Depending on the location, your outfit should be fitting to the scene, in general, most first date outfits should exude a level of elegance with a generous dash of casualness.



For ladies, wearing something that compliments your figure but still leaves some mystery to the eye is the best way to go. It is important to balance the clothing to skin ratio. Too much skin may cause your date to make the wrong assumptions. Too much clothing may cause your date to think that you are too stern or conservative and closed off from the date.

In this picture the young lady is wearing a pair of knit trousers that hugs at the waist, showcasing her figure in a subtle way. At first, you might think her outfit is a tad to serious but then you see that she is wearing a graphic tee. This combo of the trousers and the graphic tee is a perfect balance of elegance and edge. To wrap the entire outfit together, she wears a bright pink blazer that unapologetically implies a sense of playfulness.



For men, the same thing applies: a balance between sophistication and relaxation. Fellas, do not wear a tux you would wear to your sister’s wedding on the first date! Your date will feel overwhelmed either because they think your rushing them to commitment or because they think you’re way too into yourself. At the same time, you also don’t want to be too casual.

In the picture of the young man, he is wearing a pair of dark joggers with converse, a graphic tee, and a jean flannel. For a first date, this is probably too casual and may cause your date to think that you aren’t taking this serious enough. What would have made this outfit perfect for a first date would be if he wore a pair of black skinny jeans or slim, black dress pants, along with changing the shoes to a pair of suede Chelsey boots and removing the cap.

Online dating today can be very frightening, but when you are confident in how you feel and what you are wearing you’ll feel more at ease. When you are given the opportunity to be able to control something (what you wear), take advantage of that by putting your best foot forward while still showing your personality. Dating can be awkward, so break the ice with your killer style and outfit.