I spent the past decade going from 8.125, to 8.25, 8.38 and 8.5, and then going back down from there to 8.38, and finally back on 8.25.
I found that the width really doesn't change my skating but the shape of the nose, tail and WB especially are what really had me going through the madness. Changed trucks once from Indy to Venture, and from Bones to Spitfire and didnt affect me either.
I think what really helps is going to your local skateshop in person (if you have a good local by you) and comparing your board you know you hated, or wanna switch from, to the other decks in the shop, standing on a few different shapes and brands that you're interested in and that should help you make the right decision.
That's what I did with the last board I hated, figured out it was the wheelbase by comparing it to a Palace Jamal Smith board and now that's the shape I've been riding for almost a whole year now!
As for shoes, I've been collecting/wearing kicks long before I started skating so I always have like 4-5 different shoes in my trunk to skate since I like variety, could be skating Blazer GT lows one day, the next day a Lynx OG, then a Dunk High and have no issues lol