If you had only $500 to spend...

This Gucci bag is $595 which is a little over your budget but I think it's a fabulous choice. It also comes in black.
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Hmm, none of the bags I can think of in that price range right now are what I'd call "timeless classics", but Coach has some nice simple options. Think "simple", not a lot of logo's detailing, or funky shapes. A plain leather bucket hobo is always a stylish option. What about an LV pouchette accessoires? Or this Damier? http://www.eluxury.com/browse/product_detail.jhtml?styleid=10398710&SectionID=6000

Or this one? http://www.eluxury.com/browse/product_detail.jhtml?styleid=10295279&SectionID=6000
 
For $398 each, I think either of these Coach bags would be excellent. I really LOVE the pleated hobo as a classic bag that you could wear forever. The style of the satchel is fabulous, but I would prefer it in a more neutral color and leather over fabric.
 

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