A lot of wardrobe choices bear little to no effect so far. The bonuses are negligible, you still have to grind the hell out wearing this or that to get you somewhere. It took couple of months and dozens of slutty outfits presented by rando exhibitionist fans for my PC to become lustful from wearing them.They have effects.
Nun outfit gives a bonus on both gaining and losing purity.
Don't know about cowboy and sailor outfits, never used 'em.
As the clothes don't get dirty, only wet (so there is no need to change them on regular basis) and the warmth comfort system isn't seriously restrictive when the MC is wearing too lightly for the cold weather, you start to wonder why such a complex wardrobe system has been introduced in the first place. You'll do just fine with standard school uniform, swimsuit (for public beach really, with high exhibitionism you can swim naked in the lake or at school), formal attire (if dating Avery), sturdy casual wear to go and explore the world after school and something more revealing and tip-encouraging if you're looking to make money by selling your carnal charms.