Multiple categories for one menu item?

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I believe, most obvious choice would be to create two categories “Fall-Winter” and “Spring-Summer” and put four other categories in both of them. Your URLs would be like this

/category/fall-winter
/category/fall-winter/formal-wear
/category/fall-winter/night-wear

Now, to list the formal wear for both fall-winter and spring-summer on page, we have few following options

  1. Create formal wear etc as root categories, hide them in post editing screen and implement javascript to toggle them when their other counterpart categories are selected

you will get URLs like
/category/formal-wear
/category/night-wear

  1. Create pages for all 4 categories and use a shortcode (from a plugin or self develop) or write the page template to fetch posts from two categories and serve to browser.

URLs will look like this
/formal-wear
/night-wear

Someone may have better idea though…