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SEO directories, folders, categories, redirects?!

SEO directories, folders, categories, redirects?!

I am working on my friends site who has urls setup the following way:

http://www.domain.com/mens-running-and-training-shoes

http://www.domain.com/nike-mens-footwear

 

I want to put in directories/folders into the sites URLS so that they are more SEO friendly....like this: 

http://www.domain.com/mens/running-and-training-shoes

http://www.domain.com/nike/mens/footwear

 

I don't want to manually rewrite/301 redirect all the urls...

 

Is there an easy way to create these urls through magento?

Also, how do I handle/deal with products being in multiple categories?