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While the title of this question sounds like , this is not my intent.

A Shabbat guest told me then when he was in a yeshiva high school about 20 years ago, the rosh yeshiva required the boys to tie down their kippah with a handkerchief around their head so that the kippah wouldn't fall off while they played ball. They were not allowed to use bobby pins because it was considered bigdei isha (women's wear).

I was surprised to hear this ruling, as this is a new idea to me. Was or is there any opinion that rule or currently rules that bobby bins are bigdei isha?

Your answer can address the usage of bobby pins, in general, but, I'm more interested in its usage to hold down your kippa. Thus, you could address the ambiguity of begged isha. I.e., perhaps an item is normally considered begged isha except when used for a special circumstance.

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    I don't know about rulings, but wearing tichels probably made the boys look more like women than bobby pins holding down their kippot would have. – Isaac Moses May 11 '15 at 20:30
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    @IsaacMoses Pretty much my response when I heard this story! Had I been in tthat yeshiva I might have countered the rav's ruling with malbin p'nei chaveiro may be a bigger aveira! – DanF May 11 '15 at 20:33
  • @DanF don't forget this one:) judaism.stackexchange.com/questions/51322/… – user6591 May 11 '15 at 21:38
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The Sefer Bigdei Ish (pp. 244-246) quotes that R. Chaim Kanievsky was asked whether it is true that the Steipler said that wearing a (bobby) pin in one's yarmulke is considered beged ishah, and R. Chaim Kanievsky answered that he had not heard this but it is possible (yitachen). The sefer proceeds to explain that it may depend on the following:

  1. Although women use bobby pins, they do not use them to hold a kippah, but to hold their hair. Nevertheless, it may be that the bobby pin is considered feminine wear.
  2. On the other hand, perhaps the bobby pin is not considered a separate item of clothing at all, but merely a chelek of the kippah. For this reason, R. Chaim Kanievsky explained that it would not be considered beged ish for a woman to place tzitzis on her garments--the strings are not an independent garment. If so, the bobby pin too would be permitted.
  3. On the third hand, unlike the tzitzis, the bobby pin is not tied to the kippah and is not inseparable from it. If so, perhaps it should be forbidden.
  4. But perhaps it should be permitted because many men wear them to hold their yarmulkes.
  5. Yet maybe people should not have started wearing them, and even though they did we cannot follow their example.
  6. But in truth, the bobby pin is not worn as an ornament, but merely to hold the kippah in place, so it should be permitted.

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