Get rid of logos / graphic tees for outside the home 90% of the time.
I own about 15 of these Bella + Canvas TriBlend Tees. Duplicates in staple colors (charcoal grey / heathered grey / black). They are cheap, insanely soft, just fitted enough to look stylish while still being wearable by stocky guys like myself.
I wear
Cole Haan zerogrand wingtip oxfords most times I'm out of the house. Always without socks. Have them in two colors. Super light, comfortable, breathable, and I get ####loads of compliments on them (mostly from ladies).
Basic flops are okay for poolside / cookouts but spare the bare feet in stores/restaurants unless you live by the beach or are in a very casual place. Sandals are included... I avoid sandals altogether because 98% of the time they look dorky as hell.
I've been moving away from jeans toward chinos. Not normally a dockers guy but these have a nice tapered fit, have a touch of stretch to them. Got 4-5 pair in a couple colors.
I've got a few pair of shorts too but find myself wearing chinos in public more unless I'm going to be out in direct heat/sun for extended periods. Two stubborn pair of cargo shorts that are only worn when functionality is needed and I don't care about looking like an overgrown man child.
Grabbed a half dozen pair of these Bayleaf running shorts (5" inseam) for running, working out, yard work, etc. Very light weight, dry fast, good length (not too long not too short), and come lined or unlined.