I always wish I would've went to a school with uniform requirements. I can understand how wearing pretty much the same thing every day could grow rather annoying, but I would have relished the challenge of channeling a different look every day while wearing the same top and bottom. The ability to go from sweet prep to punker in plaid by changing out flats for edgy boots would be so much fun! A cute, sophisticated look could also be acheieved simply by adding some great frames, picking the right ones would be easy when using the virtual try on tool from Bonlook.
The schoolgirl look has definitely become classic, aside from Britney circa Baby One More Time and DIY Halloween costumes. It may be because plaid skirts allow for a fun, cute look no matter what year you graduated. They can be styled with a blazer or ball cap and still look super fresh.