So, I'm thinking of adding a new fall/winter handbag to the wardrobe and I'm not sure what style/type to consider. I want something lightweight so it doesn't create shoulder pain when holding it for a long duration. I rarely go out and about without a bag so I often carry one for an entire day of sightseeing/shopping.

I have a wonderful neutral gray/taupe bag already that is great as a "nicer" bag.

I usually don't go for loud colors in my bags but this one seems toned down enough (and cozy feeling to my mind). This plaid would be more everyday casual - which means most of my days. I added a few other of my fall/winter wardrobe items below from my finds - a deep olive green field jacket and burgundy moto jacket (I also use a navy moto jacket and another burgundy fleece jacket a lot in the fall). I pretty much live in jeans or olive pants - sometimes black during the fall/winter.

What do you think? Is there a better plaid option? Or is plaid not great for a handbag?