Unlike a nazir, who grows his hair for religious reasons and not as a matter of style, when a man grows long hair or a ponytail, the main concern would be the prohibition against dressing up like a woman or appearing in a way that a woman would. This concern applies to mens earrings as well. The question is whether long hair or earrings are "exclusively" associated with the opposite sex.

Another halachic concern regards tefillin. Excessive hair between the tefillin and the forehead, for example, may be considered an intervening substance that invalidates the mitzvah. However, the main problem with this seems to be with a certain hairstyle (blorit) where the hair is grown long and folded over to a place where it doesnt grow. Tefillin that lies on such a patch of hair is considered to be resting in an unnatural way.

In the case of a ponytail, while this wouldnt pose a problem with the tefillin at the front, it would pose a problem regarding the back since the knot of the tefillin would be resting on hair pulled back from the front. If the hair were let loose though, so that the knot rests on the hair that grows there naturally, it seems that it would be okay. After all, the nazir fulfilled the mitzvah of tefillin despite his long hair.

Nevertheless, from a social or spiritual point of view, it may be improper or inappropriate for an observant Jewish man to do so. First, it is not the Jewish custom for men to have long hair and ponytails; incorporating that style from the non-Jews into Judaism seems improper. Also, long hair (and hairstyles in general) normally stem from, or lead to, vanity. While its a mitzvah to be presentable, its inappropriate for a Jewish man to focus too much on his appearance and the appearance of his hair. Even those who grow side locks for religious reasons must not be preoccupied with them more than whats necessary for an orderly appearance.

According to the Kabbalah, in a spiritual sense hair is the waste product of the brain. Long strands of hair in men may act as ropes to which negative influences may take hold. This is considered particularly true regarding the hair at the back of the neck near the brain stem, which is the point of connection between the brain and the rest of the body. Harmful influences seek to attach there in order to "sever" a healthy connection between the spiritual and physical, effecting a sort of spiritual decapitation.

Interestingly, the Zohar differentiates between the rest of the hair and that at the sides of the head and the beard. This hair is said to originate from holy sources and projects positive spiritual energy: "The hair locks are shaped and hang in wavy curls from one side to the other side of the skull. This is what is written, His locks are wavy.They are situated hanging in curls, because they flow forth from great springs of the three divisions of the brain. From the spring of the first space in the skull, [Chochmah].From the second space, [Binah].From the third space, [Daat] go forth thousands of thousands of rooms and chambers, and the hairs flow forth continuously from all. Therefore, these locksare curls upon curls."

To answer your question then, 1] strictly speaking according to halacha there seems to be no prohibition; 2] as far as long hair may affect character traits, that may not be the case here, and anyway we all have room to improve; 3] most people dont conduct themselves according to the Kabbalah. Therefore, while Im not condoning long hair for men, his not cutting it off shouldnt be a reason to "cut it off". Rather, if and when you get married, patiently and lovingly encourage him to round off his observance with a more outward Jewish appearance as well, cutting off the unwanted split-ends of non-Jewish influence, and spurring new growth together from Jewish roots.

• Rav Chaim Pinchas Scheinberg, shlita, said that although he doesn't condone men wearing earrings, its not necessarily halachically forbidden to do so.
• Shulcan Aruch, Orach Chaim 27:4; Mishna Berura and Kaf HaChaim.
• Zohar, Haazinu states: 1] The hairs are places of harsh judgment, as in the verse, "for He crushes me with a tempest" (Job 9:17), where the Hebrew word for tempest is phonetically similar to the word for hair. 2] Hair at the back of the neck indicates harsh judgment as in the verse, "and they have turned their back to me and not their face" (Jeremiah 32:33). 3] There are no judgments in the hair of the beard.
• Regarding the curls of the hair on the sides of the head and the beard, see Zohar, Naso.

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