First of all, let's get this out of the way: "isn't that really gay?"
No, it's not. The first thing people judge you upon is your appearance. If you look good, people will think highly of you. There is nothing wrong with looking like you give a damn.
Where to begin: Shoes
Shoes are the most important part of a man's attire. Period. If your shoes don't match, you look goofy. Don't be afraid to splurge on a nice pair of shoes. This is what I wear, and for the price they're not bad:
1) Onitsuka Tiger by Asic - The everyday and very basic athletic/casual shoe. Comes in a whole lot of colors.
2) Espresso Black Leather by Bostonian - Round cap (toe) oxfords. These are for more formal occasions, or if there's a dress code.
3) Check out the pair of boots in the previous post. Yeah they're expensive, but Red Wing boots are worth it. Save up!
The number one rule of fashion: Fit. Is. Everything.
You can buy the most expensive clothing at JCrew or 7 For All Mankind, but if it doesn't fit, you will look awful. Make sure that no matter what you buy it fits just well enough so it doesn't look overstretched. TIP: If it's longer/shorter than your shoulders, don't buy it.
Next up: accessories
More important than your clothing is the accessory. Gentlemen of all ages should have:
1) A watch. I have a Bulova watch as I find it to be the perfect combination of price and quality.
2) An umbrella. Plain black will do.
3) A leather wallet. Any color will do.
*Optional* 4) Eyeglasses. Even if you're not near/far-sighted, check out some of the vintage eyewear at warbyparker.com
5) A nice leather belt. PROTIP: Make sure the leathers of your attire match (if you are wearing black leather shoes, wear a black leather belt).
Finally! The clothing!
That is all. Check out the essentials.
And that's just about it. Pic is simply me in your basic button-up shirt, taken in scenic my bathroom.