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Chris's hair has never looked good. For most of his adult life, Barb served as his barber. The result was a predictably amateurish, uneven cut which served as the perfect accompaniment to his clown shirt and social awkwardness. His refusal to regularly bathe, which leaves his hair greasy and unmanageable, hasn't helped. His hair has entered something of a plateau, as even when he does take a shower, his hair's appearance virtually remains the same, as evidenced by his video demonstration.
Nor has switching shampoos helped. In his early 20s, Chris used Selsun Blue for dandruff issues, then switched to Head & Shoulders. To assist with his Love Quest, he shifted to "AXE brand Freeze Anti-Dandruff Shampoo & Conditioner." When he became a tomgirl, he changed it again to Garnier Fructis shampoo and conditioner. He has also used Aussie Sprunch hairspray because "it keeps my hair poofy, and smells of candy." Nothing seems to have worked, as the photographic record clearly indicates. Firsthand observer Catherine thought it "looked like straw."
Chris, however, believes that his hair looks just fine, and has always been defensive about his hygienic habits. He also had no problem with his mother's styling. During the first Kacey Phone Call, he enthusiastically (while pretending to be Liquid) praised said haircut:
For most of his life he kept it short and didn't alter it significantly, but since the Tomgirl Saga began in 2011, Chris has taken to bleaching his hair and growing it long. Chris's natural hair color is a chestnut brown, although early photos from his childhood show that it was paler at one point. He seems to be dying his hair himself, based on the unprofessional results. The highly visible brown roots seen in pictures suggest that he did not enlist the aid of a professional stylist. Chris's hair is also evidently curly when it's long; he may have done it himself with a curling iron, but Chris is far too lax in his personal grooming for that type of styling regimen. An October 2012 Facebook profile picture revealed that Chris had grown his hair to his shoulders, and for the next couple years it remained at approximately this length.
Chris has become resolutely opposed to cutting his hair, seeing it as essential to his tomgirl/lesbian identity. In May 2011, Barb forced Chris to let her cut his hair. This resulted in Chris calling Barb a bitch. He had to wear a wig for a while. He also saved a clump of hair clippings and wore it around his neck in hopes that it would grow back faster. 
—Chris, thinking that a 1970s woman's hairstyle helps you get friends.
Chris sometimes likes to accentuate his hair with a headband, in order to cover up his bald spot. Even before becoming a tomgirl, he admired his girly anime wings to the point of incorporating them into his comic. At the pride festival and GameStop attacks of 2014, he wore a pair of striking blue and pink My Little Pony tassels. Sometimes he wears ponytails.
He dyed his hair blue in 2015, for his OmegaCon cosplay. Of course, he again failed to bleach the hair beforehand. The result is that his hair gradually turned to a sickly green color.
Chris's encroaching baldness has done little for his already uncomely appearance. Since hitting his late 20s, his hairline has been receding very quickly. When confronted in the Mailbag (17, 25 and 28) about his obviously thinning hair, Chris asserted that he was not going bald, and he was untroubled. "When it goes, and if I do go bald, I will deal with that when I cross that bridge," he declared.
In videos taken of Chris at a Fridays After Five event in 2010, a bald spot was seen starting to appear on the back of his head. By 2014, at 32, pictures showed that his hairline had receded dramatically in just a couple of years, and his hair was more poorly managed, looking even more thin, wispy and unkempt, if that's possible. While his hair is long, it has simply stopped growing on the front half of his scalp, creating an extremely bizarre effect. His attempts to brush a few locks forward do little to hide his constantly growing forehead. Catherine claimed in 2014 that it was "halfway" back on his scalp.
It should be noted that if one alters a photograph of Chris to remove his bastardized bangs, his hair looks almost exactly the same as it did before 2013 - slowly thinning and as greasy as ever.
2016 saw rapid acceleration of Chris's receding hairline. Cole Smithey seemed to begin shaving his head regularly around his early to mid thirties so the timing seems about right for Chris's male pattern baldness to follow suite. Chris's ever poor hygiene and increasingly gross neglect of his remaining and now green mop-like locks certainly did not help. Chris's current hair is less that of a transitioning female, and more of a Doc Brown mixed with seaweed.
A popular theory amongst trolls proposes that the baldness is a physical indicator of the stress Chris claims they put him through. Realistically, however, Chris just drew an unlucky ticket in the genetic lottery. Photos of his half-brother Cole Smithey show that Cole lost his hair up front relatively early in life as well, and Bob was bald too. Ominously, inactivity, poor diet, illness, and stress are well known to accelerate the balding process. In addition, there is a strong correlation between the man's age with the eventual extent of the baldness - the earlier it begins in life, the less hair will eventually remain, which does not bode well for Chris's tomgirl dreams.
Chris has never found body hair attractive, on himself or anyone else. This is probably connected to his hatred of men and their bodies, and it began long before he became a tomgirl. In 2008, he confessed that "shorts are okay, but I don't like to show off my hairy legs." A strange Yu-Gi-Oh! card shows him dressed in the costume of a female character, but deeply embarrassed, in part because the dress exposes his legs, which he depicts as covered with hair. He also claimed that "facial hair, to most women, is a Turn Off," which is his autistic way of saying that he thinks beards are ugly. Consequently, early nudes of Chris showed that he shaved his torso and pubic region.
After becoming a tomgirl, he put more effort into removing his body hair, at least initially. He told Jackie:
—Chris to Jackie
He also said he had given himself a "Brazillian." A Brazilian wax consists of the removal of all pubic hair, something Chris has clearly desired for a long time.
Despite Chris's efforts, photos throughout 2013, 2014 and 2015 consistently showed that, on his face at least, whatever depilatory measures he was taking were an utter failure, as his facial stubble - his "5:00," as he calls it, is always apparent. As with every aspect of his life, his laziness thwarts his dream of looking like Britney Spears.
Cassie, co-founder of Sonichu Girls, asked Chris for locks of his hairs so all the Sonichu Girls could have them as a souvenir.
Because Chris can't say no to a pretty lady (or a dude pretending to be one), he went to the trouble of cutting his hair and placing it into small baggies with a certificate of authenticity signed by the big C himself.
Due to the Mexican postal service, it took several months for the hair to reach Cassie. When it finally did, it was a shock - or perhaps it wasn't. Cassie described the hair as being "greasy" and having an odd odor. Evidently, Chris's hair is so filthy, the Mexican postal service, which regularly "unknowingly" ships countless pounds of cocaine, marijuana, and other illegal narcotics per year, had trouble dealing with this biohazard. Fortunately, this violation of United States Code: Title 16, Chapter 4, SubChapter IV, § 1203 (a)(4-7) did not cause any national or international incidents.
While Chris promised 200 locks of hair, only 23 were ever sent. Chris included a letter to Cassie, in English on one side and in Chris's version of Spanish on the other. Each side had a Sonichu drawing, but the Spanish side had Sonichu in a sombrero.
Gallery of hair
What Chris would look like by now if he wasn't a tomgirl.