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Is a birthstone or any gemstone for that matter kosher for a man to wear (e.g: around the neck) according to the Rabbis or is it prohibited as 'You shall not wear a woman's garment as that is a degredation' (Devarim 22:5)?

Note the connection between the gemstones and Ahaarons haKohen Gadols breastplate (if there is any, according to the wikipedia article Josephys is said to mention that alleged connection).

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    I can't see this as any problem. The prohibition is against clothing, not jewelry. Also, there are numerous men's rings that have gemstones. I can't see what would be a problem for men wearing necklaces with gem pendants. – DanF Jan 10 at 0:24
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    @DanF We learn from Lo Yilbash that a man can’t look in a mirror or shave his armpits. Clearly it extends beyond clothing. – DonielF Jan 10 at 3:58
  • @DanF Normally I'd totally agree (and I think I do) however, as you already probably know yourself, chazal had rather interesting rationaleés when it comes to prohibiting things and extending laws/commandments – Ilja Jan 10 at 10:51
  • That's true. On the other hand, numerous Chazak enactments have been reanalyzed and reversed throughout history. Chukot Hagoyim (acting like Gentiles) is a good example. How did Shtreimlach become petmisdible,? – DanF Jan 10 at 14:34
  • @DanF Oh definately, there have been enactments and most certainly there will be major revisions of certain things in the future - won't argue here. Was the Shtreimel worn in any gentile community? I thought it was decreed by the europeans for us to wear them (similiar like yellow clothing or the 'judenstern' in more recent history) in their cities and we turned this supposed act of humiliation around by wearing those items with pride - see chabad.org/library/article_cdo/aid/3755339/jewish/… ; probably an entite topic for itself – Ilja Jan 10 at 15:34

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