Okay, bud. Here is what you need to do.
Start your new wardrobe with some basics. Your first building blocks are a nice pair of good-fitting, NICE jeans, and a pair of flat-front khakis with NO front pleats or ankle cuffs.
Spend some time, go to several different stores, and find some pants that fit you well. Every store has a different cut, and slightly different nuances in sizing. You want to get a pair of both that are not so tight where you feel you are putting pressure on the fabric, but not so baggy as they slump down on your waistline. You don't want tight, you don't want loose, you want them to fit, and look good on you.
Next, you need a basic white long-sleeved, button down dress shirt. NOT a business dress shirt, but a casual white dress shirt (the material is a bit thicker). Men's bodies come in different dimensions so you need to shop around to find one that fits you. My problem, personally, is that I have broad shoulders and a narrow waist, so some shirts are tight in the shoulders, others are too loose around the waist, and it seems that when I find one that fits me well in both shoulders and waist, the sleeves are too long. GET the one that fits your body, and if the sleeves don't fit, OR if it is too baggy around the waist, you can take them to a tailor, or most any dry cleaner, and they'll fix it so it fits you perfectly.
In a nutshell, wear clothes that FIT you well. If you like a shirt, and it doesn't quite fit you, buy the larger of the two sizes and get it cut at a tailor until it fits. Don't go too baggy, if you have a good physique, don't be afraid to flaunt it. No, I am NOT saying TIGHT, I am saying GOOD FIT.
Get a pair of nice black dressy-but-not "dress" shoes, and a pair of casual brown shoes, a black leather belt, and a brown leather belt that matches your shoes.
Next, get some nice socks. The rule of thumb is to wear socks that match the color of your pants, but with jeans, you can either wear a light grey or white is okay too with more casual shoes.
Pick up a good cologne to give the new you a new and fresh scent.
And, there you have it. You have the basic building blocks for a classy male wardrobe. From there on, it is just a matter of adding things on. Perhaps the next purchase is a good pair of black slacks... dark solid shirts look good with the black slacks, and black shoes. With the khakis, lighter shirts or patterned shirts fit well, and you can easily turn any of your shirts into more of a casual look by wearing them with the jeans, and some nice shoes.
I know that some of you are reading this and saying, damn, Gardener is gay, but unfortunately for your assholes, I am not. I had a pimp grandfather who taught me to never leave the house ungroomed or unkept. He said, you never know what is going to happen that day, who you will run into, or what kind of an impression you are going to make on someone who might become important in your future. First impressions are everything, and your appearance is something well worth paying attention to.
