I never know what to wear on dates! Do I wear a dress? Just regular shabbos clothes?? I never know if I’m “doing it right” and whenever I come back from a date, I always feel I should’ve either been fancier or less fancy…I just don’t know!! Thank you!
Your question is a very common one. Growing up, when getting dressed for Bas Mitzvas, Chagigas…. my father always told us that when in doubt, you’re better off dressing more up than down. I think this is important when it comes to dating. You’re better off looking more dressed up for a date than not.
However, you still don’t want to make a fool out of yourself and it’s important that you feel comfortable, so here goes the “rules”: For the first and second date, dress VERY nice. This means not weekday not wedding and not chol hamoed. Generally, it would be how you dress on Shabbos. Once you get to the 3rd date, then you veer away from the Shabbos clothing and go for the VERY nice weekday. Stick with the very nice weekday till the end. This means short skirt, tights, nice top or short jumper/dress. When it comes to repeating shoes or outfits, I personally would say switching off shoes is good but I tried to wear something different on all 15 of my dates. Yes, I did have to borrow from friends, but I felt funny repeating. I would say to repeat something from an earlier date would be OK too though.
Another thing to keep in mind is what is HE doing? It’s perfectly normal after the first 2 dates to ask the Shadchan where you’ll be going and if he’ll be wearing a tie. Generally, if he’s wearing a tie, you go with the nicer clothing (Shabbos), not ties would mean more casual (very nice weekday)
Hatzlacha and I hope this was help!