"Hi! I'm actor Troy McClure. You may remember me from such clothing related websites as, "Hats Across America" and "Boxer Shorts: Friend or Foe?".The webmaster here, Andrew, asked me to come and say a few words about one of my favorite topics, socks. Most baseball players wear socks, because if they don't, they get really nasty blisters. Socks are one of my favorite articles of clothing because they are so useful. You can keep your feet warm, you can..ummmmm....well, I'm not really sure.I need to go since I'm starring in the new educational film,Vegetarianism is Murder,so enjoy this page, and I'm Troy McClure.See you in the filmstrips."
This is Johnny Evers of the Chicago Cubs, circa 1908. As you can see, he is wearing the style in fashion at that time. His pant legs are tucked into his socks. Very interesting.They are actually comfortable though, since that was what I did on cold days in PE, when I wore my sweatpants.
Out with the old and in with the new, eh? Wait a second.....the Indians' Jim Thome is wearing his socks in much the same style as Evers did, 90 years prior! But it really isn't. Rather than tucking the pants into the socks, the stirrups are pulled up really high, giving in to modern convience and the ever popular, "Retro" look.
Many players nowadays find high socks to be the best way to wear them. 
Observe the Braves' 2 Jones', Andruw, the outfielder, and Chipper the 3rd baseman as examples.
Fashion isn't the only reason that baseball players may wear socks out of the norm.Just consider the Cardinals' Delino DeSheilds. He wears his socks depending on how well he is hitting, he considers them a "lucky charm". DeShields isn't the only player that practices this philosophy. The Astros' Derek Bell, and the Cubs' Mark Grace and Brant Brown, have been known to hike up the socks for good luck.
Brant Brown is the Cubs centerfielder and he wears his socks according to luck. He wears them high according to whether he needs to feel lucky.
. Apparently they work, because the day this picture was taken, he hit 3 home runs!
But in the end, regardless of what socks you wear, high, low, depending on hitting, or just plain regular, like the Brewers Jeff Cirillo, it all goes back to our National Pastime, Baseball.