I’m about to begin a project in Java where I’m essentially making a dumbed-down iTunes clone. I will be using Swing to make the GUI, but I was wondering the best way to style it in a way similar to iTunes beyond just changing colors/fonts/borders. I have looked into using CSS along with Java Swing, but any resources I’ve found are out of date. Are there any new ways to approach this? Or should I be looking into something besides CSS?
Here is the design I’m looking to implement via Swing (the basics at least):

There is no CSS styling with Swing. If you use JavaFx2 however, which is the successor of Swing, you do have CSS styling available to you.
If you are not already very familiar with Swing, I suggest you consider JavaFX. The latest 1.7 versions of Java has JavaFX 2.2 built in. It has CSS support and a Media Player
It is of course possible to also do it in Swing. There are many differnt approaches you could use, but to give you a starting point, here is how I would go about to create the buttons. This approach requires Java 7, but if you use JXLayer instead, you can also run it in previous versions of Java. The buttons are a combination of 2D paint and some icons I had access to. Just change it with icons you have. The size of the circle will resize itself, depending on the images you are using.
When you click the buttons, you will here a beep sound, and the appropriate text is printed to console. Generally speaking, JLayer is very useful for styling you Swing applications.