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mommamia22
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Could you please elaborate about what you learned (“you will be chased by fire”)?

In terms of switching from wearing a wig, you might find it easier to do so gradually. Try wearing a really wide headband like the chassidishe women wear. It covers a large portion of the top of the wig and will allow you to get used to that look. Try to wear a hat fall, also. If the wig hair isn’t too long, and you wear a hat or a tichel on top, revealing only some of the hair, you will get used to that look. Wear earrings also, as you will feel more feminine when you show less hair. I think feeling comfortable with a look has a lot to do with those we see and hang out with. Look for women who wear tichels in a way that you admire. They will be more than happy to show you how to tie it in a really nice way, and you’ll see others who are doing it too.

You can also try wearing a tichel for brief periods of time to get used to it: shabbos, early mornings, etc.

They used to sell something called a pony tail snood. It looks like an extra large barrette with a fabric bag attached to it. You might be able to make one yourself, if you can’t find one. They’re really useful. You can put your hair in a low ponytail, snap the barrette on and put the pony in the bag. Then, plop a deep hat on top, which will fully cover your hair. It’s a pretty decent compromise, looks more up to date, and may help you feel more feminine.