S.O.S! The Date Debate

Dating is great until you get out of the shower and attempt to find an outfit to wear. So let’s restate that…the idea of dating is great.

People always freak out about what to wear on a first date because, alright let’s face it, the first date requires a good first impression (if you want a second date). Right? And since the two of you don’t know that much about each other, your appearance is a big deal on a first date.

Here is my best advice for a “first date outfit”: KEEP IT SIMPLE, WEAR JEANS. This is so important. And this nugget of advice can go for men and women. It seems silly, especially coming from someone who only wears black and rarely wears pants in general. But, let me tell you why wearing jeans on a first date is a good idea: you can dress them up as much as you want, but you’ll still look somewhat casual. You can wear any type of shoe with jeans, boots, heels, flats, oxfords, anything. Jeans look good with just about any shirt or jacket. And, arriving in jeans and a nice top says “I’m excited and feel great but not trying too hard”. And see, right there is the meat of this post, “not trying too hard”. Yes, daters like to see their other half looking nice, but it is completely and utterly obvious when you have just tried to hard to look good for a first date.

So, moral of the story? Wear jeans! And save your LBD and Hermès pocket square for the second date.


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