Everything about PS is ugly and clunky, everything. The glasses (a BIG improvement over my own Age of Dinosaurs), the haircuts, both men and women. Everyone's faces break out in the heat and humidity and stress of the Annapolis summer. You can wear your own running shoes most of the time that you run now, but you sometimes have to wear the issued ugly "go-fasters." How they manage, year after year, to choose the style most likely to be favored by the wearer's grandparents is a mystery that still fills me with awe. The underwear is ugly. Women can't wear makeup, and if tradition holds, most women give up shaving their legs (during PS) because it just takes too much time when you literally have 30 seconds to 1 minute to shower. Priorities. As for the glasses and underwear and ugly shoes, the Navy does not have an unlimited budget - they, too, are at least partly under the lowest-bidder gun.
But here's the thing too. Every new class of plebes (and new recruits at RTC) comes in thinking that looks matter a lot. When you're 17 or 18 or 19, looks are everything. You're constantly looking other people over, and you know they're looking you over too. I would not be at all surprised if part of the function of the ugly glasses, underwear, not enough time to shave your hairy legs etc. is an important part of training. It teaches people priorities, and most people quickly learn that superficial looks do not matter nearly as much as they thought. It teaches plebes and recruits that their mission in the Navy is different from anything in the civilian world. In the Navy, you look out for your shipmates and get the job done, period. No one cares (then) if your glasses or haircut are ugly - do the job and accomplish the mission, and you value shipmates who behave the same ways.