Right out the gate, I’m going to leave my cards on the table. I think it’s a bad idea for a man to instruct a woman he’s dating on how to dress, so my first piece of advice is: let it be, for now.
Now that doesn’t mean you’re wrong to be uncomfortable, because the question you’re asking combines two fraught issues: the first being religion and modest dress, and the second being blending in with a significant others’ clan. My blood pressure is rising just thinking about it.
To me, the question is: are you trying to protect your date or your family? If you’re trying to protect your family from an immodest dresser, I don’t feel great pity for you or them. You chose to leave your observance behind and date this woman, they chose to accept your choice, and if you’re still judging her from their perspective, you need do some work to let that perspective go, fully.
If you’re worried that your date will be embarrassed when she shows up in her avant-garde attire and sees everyone else in their frumpy frum fashion, you can gently warn her. You can show her a picture of your family if she hasn’t met them, and presumably she’ll notice how they dress. Or you can tell her that you’re anxious about your family judging you and ask her for advice on what you should wear. At that point, you’ve painted a clear picture for her and it’s her choice how to proceed. Eventually of course, if you two fall deeper in love and more latke parties are in order, she may want to adapt her outfits to the occasion. She may not. Either way, it will be up to her.
Sarah Seltzer is the Editor-at-Large at Flavorwire and a longtime contributor to the Forward’s Sisterhood Blog. Find her on Twitter @sarahmseltzer.