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Controversial in the stylish thread but I find a decent hip/bum bag solves this issue any you can carry heavier stuff more comfortably. As someone else has mentioned a loose top with stuff in pockets will likely flap about.
My Patagonia black hole with any T shirt, Swrve shorts and obviously ice white socks with navy blue double cadet stripes is my current favourite sports casual combo.
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Who's selling jerseys that don't look like bike kit with with the convenience of rear pockets?
Ideally priced like the morvelo but subtle like Cafe du cycliste...
https://www.morvelo.com/collections/mens-jerseys/products/movin-overland-dual-short-sleeve-baselayer-jersey
https://www.cafeducycliste.com/en_uk/men-gravel-jersey-betty-white-navy.html