We study, numerically, the self-similar propagation of optical pulses – similaritons – governed by the non-linear Schrödinger equation with fractional-order dispersion and constant gain. Whereas in the classical, integer-order limit a Gaussian input relaxes to well-known parabolic similariton, we show that fractional dispersion, controlled by the Lévy index, fundamentally reshapes this evolution. As the Lévy index is reduced below its classical value, a standard Gaussian input evolves into parabolic, flat-top or two-peaked profiles, the last of which is a genuine consequence of fractionality and is absent in the integer-order case. We trace the physical origin of this two-peaked, hollowed core to the singular low-wavenumber behaviour of the fractional operator, and we demonstrate that it is suppressed in two distinct ways: by increasing the gain, which drives the pulse onto the parabolic attractor, and by broadening the initial condition, which reduces the reshaping that the pulse must undergo. A sufficiently stretched Gaussian input restores clean parabolic self-similar propagation across the entire range of fractional orders considered. Finally, we show that fractional similaritons develop pronounced, algebraically decaying heavy tails – in stark contrast to the exponential localization of the classical case – whose power-law exponent is fixed directly by the Lévy index, providing a clear signature of the underlying Lévy-type transport.