My middle school encourages "professional attire". A lot of the male teachers wear ties. I wear skirts more frequently in warm weather, but during winter it's easier to wear pants- dress pants or something like khakis. Fridays we can wear jeans and school shirt (tee or polo).

I often find it really difficult to find clothes that fit or flatter- even when I'm willing to pay $$, (which I can't afford to do most of the time). At 5'1" and with a generous bust and very short waist, a lot of clothes are just not proportioned for my shape. Even petite sizes seem to be cut for much longer torsos and fewer curves. Pants are generally easier to find, especially since I've lost weight. And shoes! A bunion/arthritis in my foot eliminate about 90% of all shoe styles as impossibly uncomfortable- especially narrow toes and high heels.

All that said- this discussion is making me want to go shopping for a some new clothes.