There are a lot of photos that were purposefully edited or shot in a way that made it look just absolutely abysmal, but in reality? It was a damn good look.
Should also be noted, this wasn't an entirely spur of the moment thing as everyone tried to make it seem. She had actually scheduled and sat down at her stylists/hair dressers office, and told them she wanted them to shave her head — but they wouldn't do it, tried to convince her not to do it, and so Britney ended up doing it herself, which is why the original photos were rather horrible — she was shaving her head for the first time, not using the proper tools, and didn't get every spot, or anywhere close to even.
I've been shaving my head for ten years now, and it took me a good two years to do it properly, and I still mess up fairly often.
She talked about it in 2008 by saying:
“I was going through so much artificial stuff with my kids and Kevin at the time [her ex-husband had just taken her kids from her]. He’d just left me and I was devastated... People thought that it was me going crazy and stuff like that, but people shave their heads all the time. I was going through a lot, but it was just kind of like me going through a little bit of rebellion, or feeling free, or shedding stuff that had happened, you know?”
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