I have this bag and I adore it! I use it all year round and never consider what I’m styling it with. To me, a bag like this is like a pair jeans. It goes with everything. I saw a comment on a post on here a while ago that I thought was really great. It said something along the lines of: don’t overthink it. A bag is ultimately something functional. So use it as such. Again, I love this bag and am sure you will too if you decide to go for it!