Shaving it all off is the new comb over. It's more likely to detract from machisimo than improve it. It's patently obvious that nearly all that try it aren't, and have never been, Skinheads. These days it's so rare to see male pattern baldness that someone with a shortish natural haircut would definitely stand out from the crowd, and perhaps communicate an IDGAF atitude.
I should beware topology iiwy. The homology of the partition algebras lurks there, waiting on the unwary…
Matching a man's wardrobe to their evolving hair colour/style/follicle count isn't something I've ever considered. Is this a normal thing? (with apologies if accusations of normality shouldn't ever be levied at an uncloseted eyebrow sweeper.)