Last week, I talked about some general dating fashion tips, but this week, let’s get specific. How do you know what kind of date calls for what kind outfit? Check out the list below for some guidance:

Coffee date: Asking someone for coffee means “you’re a decent online conversationalist, and I’m ready to meet you in person, but I’m not willing to commit to anything involving time or money in case we don’t click in real life.” Due to the casual and brief nature of the coffee date, you’re allowed to look casual. However, because of the brief encounter, your first impression is even more important here. This means that you should take care to look good and presentable, even if you’re wearing casual clothes. Do not wear gym clothes, leggings, or anything that shows you clearly stopped by the date on the way from an activity that involves sweating.  A sundress, jeans, or a sweater dress and boots in the winter is perfect.

Drinks and/or dinner: I put drinks and dinner in the same category, because, if a drink date goes well, it will often lead to dinner.  Assuming this dinner date doesn’t involve a drive-thru window, look extra nice!  Ladies, this means a dress and heels (unless your date is shorter than you, in which case, use your discretion), or something equally dressy. Guys, slacks and a shirt always work – and tuck it in and use a belt!

An “activity” date: This can include bowling, hiking, rock climbing, or any extreme adventure from The Bachelor that doesn’t actually happen in real life.  You will be moving around, so you want to be comfortable (i.e., not pulling up your strapless bra or tugging at your dress), but this is NOT an excuse to wear some ratty old gym clothes.  ‘Athleisure’ is a thing for a reason.  Leggings (in good condition) plus a bright colored top and tennis shoes will do for the ladies.  Guys, clean clothes without holes and tennis shoes in good condition are acceptable. You might decide to go to a casual restaurant afterward, so make sure your outfit is versatile.

Wild card: In this scenario, all you know is that you’re getting picked up at 8. You aren’t sure where you are going or what you’ll be doing.  Unfortunately, you must be prepared for a multitude of situations.  You should be safe wearing something on a level between your coffee date and dinner date.  Wear semi-comfortable shoes in case you end up walking more than expected, and for either gender, you can’t go wrong with nice jeans and a cool jacket.

One Comment
  1. If you really like each other, who cares what you wear? On the second date, I put an engagement ring on my dates finger. And we are Reform, not from the Frum

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