Generated a 1kHz square wave in Audacity and normalized it to 0dB (fs = 44100Hz):
Added a 24dB/oct high pass filter (std Audacity plug-in), cutoff frequency set to 100Hz. Result:
Zoomed version:
Why "clipping" so badly?
EDIT: When normalized to -3dB before filtering there's no "clipping" present.
Filtering same signal with low pass filter does not have this issue.