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Has anyone run across a problem similar to this or do any of you know of a website that uses png images in a similar method to this one? Any help is greatly appreciated. This has caused quite a few headaches and some teeth gnashing as it is.
If you use div tags set to absolute or relative you can give them a "z-index" value. what this means is the highest z-index value will be the one on top.
So if the basic shirt div tag was called "basic" and the logo div was called "logo" by just changing the z-index value on either you could swap around the images.
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I'm assuming your logo has a transparency. If you're using a png with alpha transparency you may want to check for browser support. IE6 for example does not support this except through a hack.
Use the shirt as background image in a DIV and insert the logo using the img tag into the DIV as the "ovelay" should give you consistent results in any browser.
If it still fails you most likely have a problem with alpha transparency support mentioned above.