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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.
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