Luckily pages rank for many keywords/phrases so the short answer to your question is yes it's more than possible to rank for both keywords.
The issue will be timing really, the 1st phrase is not an issue and as you say its already ranking #1.
The tricky bit will be the changing 2nd phrase and how quick you want it to change, I normally allow a full 6 weeks when making changes to see the full effect, so it won't be like ok tomorrow we want X to rank.
I would refrain from building external links for the 2nd phrase as you will want to change these links for each season. So I would build quite a few internal links, as you control these then when the product changes then it should be simple to switch the links anchor text to your new product text.
I would also add schema if you have not already for the product so google fully understands there is a product on this page.
I am assuming in this case we are talking brand/product but only 1 product per season.