Yup, it all depends on the context. The problem occurs when you submit to sites that don't want to spend the time to evaluate the context and just ban all use of the word.
I list quite a few
schoolgirl galleries on my TGP's, but most of the time their age is far closer to 40 than 20. For example:
Mature Domme Schoolgirl 
Quote:
Originally Posted by D2222
IMO School girls in pigtails and catholic school uniforms = trouble getting listed
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Again, it's all in the context, which includes the set and other props in the photos. Pigtails are OK, so long as their isn't an obvious attempt to make the model appear under age. Add in some teddy bears, dolls, frilly pink bedroom, and unless the model is quite obviously older I won't list it either.