Besides being cheap, ugly, poorly-built, designed to wear out quickly, and the universal symbol to women that you have no idea how to actually dress, nothing.
So you throw down $200 for a pair of Kenneth Coles. With heavy use they might last you a year or two, because they have rubber soles and they're glued together. More on that in a minute.
A few things. Let's talk toes.
First off, your feet are not square. Grown-up shoes -- Alden, Allen Edmonds, Peal, Bergdorf, Paul Stuart -- are built on different types of lasts. The last is the part under the footpad and above the sole. Fine shoe manufacturers build different models on different lasts because people have different toe shapes. When you find a last that fits your foot, it will change your life.
Square-toed shoes were developed so that shoe manufacturers didn't have to build on multiple lasts. As a result, they don't fit anybody as well as a properly-lasted shoe will. This is why your feet hurt after standing all day and mine don't.
Secondly, grown-up shoes are welted. This means the soles are stitched to the last instead of glued. Because of this, they can be resoled after a year or two, for about $20. Also, the heels are nailed on. New heels cost about $10. The entire shoe can be dismantled after 10 years and the leather can be re-stretched, making it look practically brand new again. Also, since the leather is of a much finer quality, they will develop a patina as they age, looking better every year instead of cracking and wearing out. Your $300-500 grown-up shoe can, literally, last you for your entire working life, during which it will form itself to your foot with the suppleness of a broken-in baseball glove and look amazing. All this for the same price as two pairs of cheap shoes that you have to throw away every couple of years and that hurt your feet anyway.
Most square-toed shoes are cheap, and deservedly so. Kenneth Cole is odious because they charge almost as much for glued-sole square-toed one-last shoes as many handmade shoe manufacturers charge. And they still look cheap. I picked up a pair of Alden wingtips in my favorite last at Nordstrom Rack a few weeks ago for $150.
Square toed shoes show anyone who knows about shoes -- and all girls do -- that you don't know anything about shoes other than maybe "black shoes = dress shoes." Square toed shoes are part of the dress uniform of a twelve-year-old at a wedding, as well as the universal sign in the business world that you just got your first-ever job that requires a tie.
That's wtf is wrong with them.