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Vans Classic shoes usually, with the insole removed and pro custom insoles added, some super glue on stitching and high wear areas, often black spray can over whatever colours are on the side of Old Skool and Sk8 Low versions more recently as they have been on great sales, which also helps the shoe hold up I have noticed. I have others in rotation, like Half Cab Classics, some older versions of Pro Eras and Old Skools, but they don't usually get out much. Mainly the Classic shoes with the custom insoles for everything skate related.
Jessup is the only grip I skate, don't dust it back at all and if I was to skate the one pair of shoes completely, non stop, they last a couple of months until they are bald and then retired from active duty, but are still used as go to shoes when skating a new board at home on the ramp.
Might set up a new board every week sometimes, or go back to older decks I have taken off for a while, so the grip is usually about medium on any board I have, but I also never wear the grip right out, so it all works really well for me - soft soled shoes and plain Jessup is a great combination.
The top tends to wear a bit more or less depending on what I am skating, but usually more park, transition, my ramp at home, or some minimal tech stuff, so I don't blow out the top, or at most, the bottom is usually fairly done by the time the top blows out as well, so I do moderate what and how I skate depending on a number of things, skate a bit most days, some solid sessions a couple of times a week at various places, or just a simple roll at home on rainy days or when I can't get out to go anywhere else.
I think that covers it, but the basic Vans gum sole and Jessup has been my go to for a long time and I think that over anything else has been the main thing that has never changed for me, or at least feels like home, more than anything else.