You CANNOT skimp on shoes. A lot of guys will blow hundreds on a suit and skimp on shoes. This is very silly, as you spend all day on your feet.
Shoes are an investment. A good pair will last you your whole life. Bad shoes will ruin it.
Bad shoes are glued, made with inferior leather, and are generally not durable. Stay away from fashion brands, especially Kenneth Cole. The shoes, while some might think stylish, are bottom barrel when it comes to quality.
You will probably have to spend ~$300 on a GOOD pair of shoes. They will likely be made in the US or in Italy. That might sound exorbitant, but think about it. If you spend $300, and the shoes last you 20 years, that's $15/year.
For starters, you want a plain, black, captoe balmoral shoe.
I took this post from a blog article I wrote last summer:
There are two main different styles of lace-up shoes: Balmorals and Bluchers. They have a huge amount of history behind them which you can read about on Wikipedia. I am just going to give you the very basics.
Balmorals are also known as closed throat shoes. Because of the way that they are constructed, the lacing area of the shoe (the vamp), forms a V shape. It looks like this:
The Balmoral is a more formal shoe and is appropriate for suit wear.
The Blucher, or derby, is a more informal shoe. The lacing is "open throat," meaning that the leather that holds the laces is a separate piece that is sewn to the shoe. It looks like this:
Derbys are normally more appropriate for casual wear with a jacket or odd trousers.
The ideal basic shoe is a black balmoral captoe. A perfect example of such a shoe is the Park Avenue by Allen Edmonds.
It's a traditional, conservative shoe that will offend no one, is made in the USA, and is constructed in a way that will last you 20 years or longer if you take care of it. Additionally, Allen Edmonds offers shoe recrafting, so if after those 20 years your soles are looking a little ratty, they will resole and recondition the shoe for a nominal sum. If the Park Avenue's a little too stodgy for you, try the Soho. It's a little more elongated and younger looking.
Allen Edmonds come with a bit of sticker shock initially (~$200-350), but they are absolutely worth it compared to cheaper shoes that will either fall apart quickly or be less comfortable. You can also always check out eBay for secondhand shoes (I've nabbed my AEs from Ebay or Styleforum.net's buy and sell forum for really inexpensive) or Nordstrom rack for shoes at a large discount. You can almost always find discounted Allen Edmonds somewhere. But make sure you buy the right size.
What Should I Avoid When Shoe Buying?
These are just my opinions.
Avoid Kenneth Cole-ish designs or anything with square toes. Like this:
These shoes are bad for a number of reasons:
Companies make square-toed shoes because it's cheaper and easier than making a good rounded toe shoe. They pass it off as fashion, but it just makes your feet look like Frankenshoes, and they laugh at the increased profit margins. Moreover, they are normally made of inferior leather and have rubber soles. Besides, a slender shoe with a rounded toe actually elongates your leg and creates the illusion of height.
Look for leather soles on shoes.
While it's not a perfect indicator of quality shoes, normally leather soles mean that a shoe is constructed a little better.
Don't Buy Shoes Made in China, India, Or Brazil.
Moral qualms aside, shoes made in these countries are generally thrown together very poorly with inferior leather, shoddy finishes, glue, and poor craftsmanship. Fashion brands, for example Steve Madden or Banana Republic, make their shoes here to save money, not because they make good shoes. It really is good to buy American shoes. Allen Edmonds are relatively affordable and are a deal on sale. Aldens are the top of the line ready to wear American shoe, but unfortunately are out of most budgets of law students by a few hundred dollars. Check out eBay or the Buy and Sell forums on Styleforum to get some good shoe deals. Ferragamos are nice, but they're much more expensive and not as solid as their American counterparts.
Gentlemen, until next time, happy trails!