People with inferiority complexes attempt to hide their perceived defects. They end up looking worse than they would if they chose not to cover them up. What else is he hiding? Trump could wear a wig or toupee for his obvious thinning hair. He hasn't, and simply works with what he has.
They are both doing the same thing, but you have a different standard for one over the other. DeSantis may be overconscious of his height and Trump is overconscious about his hairline and they both take steps to hide their inadequacies from the public.
It would be a point of leadership for both to state that they have an inadequacy, but they aren’t going to take steps to hid it.
It’s an issue only for those that want it to be an issue. Personal vanity stuff is not an issue for me. Trump can strategically over comb his hair and DeSantis can wear heels.
As long as there are no other problems.