What Should I Wear?

By | March 21, 2013


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!

8 thoughts on “What Should I Wear?

  1. chaykie

    definitely helpful! i’ve heard the other side of this tho, which kind of also makes sense i guess. dressing in regular shabbos clothes in the beginning, then getting a little casual, but by the last couple of dates (when you both know its headed toward engagement, do the fancy clothes, cuz it’s more special, and it’s a very special time. i’d usually stick to your suggestion mentioned above, but what do you think about this one?

  2. d-e1-9

    I disagree. I think that as long as you look nice, it doesn’t matter if each outfit is different. I think the thought of putting so much time and effort on the Chitzonius is the wrong attitude when the emphasis of the dating period should be on the pnimius.

  3. chaykie

    ok, i agree with you to an extent, de19, but as girls, we like to look pretty, and be dressed up and mature looking, and all that stuff- so as long as ur not going overboard or obsessing over it to the point where u make urself really stressed over it, then i think it’s fine to put time and effort into it. you wouldn’t want a boy coming to your house with signs that he didn’t take the extra time and effort to shower, shave, dress nicely… paying attn to chitzonius is not a bad thing if done properly and for the right reason.

  4. dance4ever

    i think for the first two dates dress like you would for a vort- a little dressier than shabbos…

  5. rosepetal5

    What about the girls who don’t have such huge wardrobes? What if they are not all that fashionable, or what if they can’t afford so many clothes? They might not have the option to wear something different on every date.
    And in terms of borrowing from friends, everyone wears such different sizes. Borrowing and sharing might not be possible.
    I also don’t see the distinction between “Vort dressy” and “Shabbos Dressy.” Anyone care to explain?

  6. Ts91

    I think reson this is such a commonly asked Q is b/c it really depends in were u live and the typ of boy u are going to date. Like for me I live in isreal you cant were heels on a date. For one u will look waaaaay to over dress and in some circles not tznius. I think the main thing is to get a feel for ur comunity/ the typ of boys u are dating and go from there. What I usally do is a nice shabbose skirt w/t a very nice more casual top w/t my hair and make up like i would do for shabbose. Just keep in mind no madder what circle u r in and how big ur wordrobe is makeup, hair, shoes, and jewlery can take an outfit from office atire to some thing you can were to a wedding. like a black dress paired w/t heels a statement necklace bangles shimery eyeshadow full blown hair and a belt can be worn to a wedding wile that same dress with flats simple makeup ur hair pinned back and a cute cardigin can be worn to the office.

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