Imagine: It's 1956. You've gussied yourself up for your big date at the high school prom, happening later tonight. You've shined your shoes, slapped the Pomade in the hair (for a nice, clean look for your tightly buzzed hairstyle) and your ruffled tuxedo is all pressed and smelling peachy. You fasten your pocket watch to your jacket, and after a lecture from your father and mother about the dangers of staying out too late, they give you the keys for the family station wagon. A nifty-doodle ride for a nifty-doodle date! You swing around to pick up your date (named Ethel, of course) at a somewhat late 6:30pm.

Arriving at the prom, you raise yourself out of the paneled station wagon, open the door for Ethel, and skip up to the door with glee. Your friends from the Latin Studies club are there! Keen! Suddenly, as you cross the parking lot, your whistling of "Jesu, Joy of Man's Desiring" is interrupted by a shrill, piercing cry from the group of greasers, rockers and bikers smoking in the opposite corner of the parking lot:

"Hey, look at the square!"

You don't understand! How could they not appreciate your safe and normal choice of clothes, music, and standard of living? And where exactly does the term "square" come from, anyways?

Looking back in the history of square-ness, we come across a very interesting change of terms (started by none other than your choice of footwear) that will at least answer the last of your questions, young square-- err, I mean squire.

Imagine: It's 1836. You've fancied yourself up for the big social at the University, happening later tonight. You've shined your favourite old pair of square-toed shoes, added some wax to your fined groomed moustache, and your ascot is as dark and understated as it can be. You fasten your pocket watch to your jacket and, after giving a lecture to your students about the dangers of staying out too late, you stroll out towards the University grounds. A most superlative evening for a most superlative social! You wouldn't dream of taking a date (except perhaps Elizabeth, your cousin from the North), so you head across the fields alone.

Coming up to the great hall's doors, you see your friends from the conservative camp in the hallway. Heading towards them, your whistling of "Jesu, Joy of Man's Desiring" is cut short by the sneering remark from the liberal group of members of the University's student panel standing behind you:

"That sir, is the prime example of one with square toes!"

So now we see: the colloquial term "square" is actually derived from its forerunner, "square toes!" The term described a formal, precise old-fashioned person, most usually of the conservative persuasion. The term itself was derived from the wearing by gentlemen of the "old school" of the square-toed boots of their younger days. While the attachment to outdated footwear has been lost, the connotation of "squareness" has lived on through the language.