All Ayami's Belmonts have heels and pointy boots. Hell, even Soma has Heels and pointy shoes.
Trevor is really the worse offender.
I think only Alucard's boots are somewhat sensible looking. (Maybe Juste's too)
I can understand Juste, somewhat. And I can definitely understand Alucard.
Trevor and Simon? Not so much. They didn't even make pointy boots at the time (but I'm ignoring that since Castlevania is quite anachronistic in its choice of outfits).
They just don't fit the character. I guess I'm still thinking he should still be barbarian-like. The Ayami Kojima design... it's like it half-asses one thing and goes too far into another. I can see that she had a tough time merging her vision with the designs of old, as it shows in the way some parts of her design don't fit (in my opinion).
Barbarian Furry Boots ... cancelled by ... fashionable pointy tips.
Ancient Leather armor ... cancelled by ... it has a choker turtleneck top.
Roman-Style Studded Leather Belted Skirt ... cancelled by ... only covers half of his body and the other half shows his studded leather tights (wtf).
I actually dig his facial features, and would probably just superimpose 'em over the X68000 Simon and other old Simon designs like the way Jago did it, haha.