There is no simple answer because it depends on the nature of the loads, the application, economics and other factors. For industrial applications, I would size the transformer such that its maximum forced-cooled rating is slightly larger than the highest peak demand expected. Plus whatever allowance is appropriate for future growth.
For a hospital I would be more conservative and probably size based on connected load unless this was clearly unreasonable. As a minimum, I would size such that the transformer could carry the maximum expected peak load continuously at its self-cooled rating - no reliance on fans.