I think it truly depends on the player ... some people can make just about anything work =)
With shorts, the traditional (e.g. 52005) is just a staple and I really like the new sport saddle (e.g. 52070). I'd also have no problem rocking the sport saddle with BOA either.
Here's where for me 'it depends'. I would have no problem with an all white shield tip (52096) or asymmetrical (52138) with shorts, but I would have to save contrasting colors in our shield tip (e.g. 52112) and asymmetrical (e.g. 52146) for pant days.