URLs for products under multiple categories

Hello,

The temporary URL of the site I'm working on and need help with is here: http://skinfitusa.wpengine.com/ It will be the updated/wordpress version of the current site: http://www.skinfitusa.com/

The new site needs to match the old/existing one as much as possible, including the link structure. But I'm having some trouble with the Store and Product URLs.

As you can see on the old/original site, there are a lot of Shop categories (Shop > Men, Women, By Sport) and subcategories (Men > Triathlon, Women > Triathlon, etc.) and a lot of products fall under multiple parent categories and sub-categories.

For example, on the old/existing site, you can navigate to SHOP > MEN > TOPS > [then click the first product on the top-left] and your path will be this:
http://www.skinfitusa.com/shop/men.html
http://www.skinfitusa.com/shop/men/tops.html
http://www.skinfitusa.com/shop/men/tops/aerossshirt.html

But on the new wordpress site, getting to the same product is this... and what I'm trying to fix:
http://skinfitusa.wpengine.com/shop/
http://skinfitusa.wpengine.com/shop/all/category/men/
http://skinfitusa.wpengine.com/shop/all/category/tops-men/
http://skinfitusa.wpengine.com/shop/all/test-product-aero-ss-shirt/

1) Is there a way to simplify the URLs and get them to match up to the old site??
2) Is there a way to create a new category with the same slug as another, as long as it has a different Parent category?? See the screenshot of my current set up. I'm not sure what else to try... please help. :slight_smile:

Thanks!