I've been living in leggings and athleisure for the past decade. Kids now in middle school, and I just started wearing jeans again! So excited, but not sure what bag works for jeans. (I usually carry around my Trader Joe's cotton tote bag. I'd like to look less sad.

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I normally wear jeans, a tucked in breton shirt or plain neutral cashmere or cotton sweater, and black leather sneakers or chelsea boots. Super basic because I don't know what else to do. Fashionistas, please weigh in.
1) Does this bag work with everyday jean and sneakers?
2) Is this this lighter color is only for summer and maybe I should opt for taupe for year round versatitlity?
3) For when I do opt for athleisure/hoodies, what bag can I wear besides my TJ tote. Like, my only other bag is a black fanny pack. I know I can do better...
Below is the Polene Neuf in Chalk, FWIW. Thanks thanks thanks for advising this clueless mom.