Look into the White’s Oxford or Derby. https://shop.whitesboots.com/all-boots/ I’m also a big guy with big feet and I was in Retail management for nearly a decade, and I would not recommend Redwing for comfort. We walk literally miles every day on concrete covered in linoleum, and that is not comfortable in any redwing I’ve worn that would also look nice enough to wear in management. (A big wedge sole moc toe boot is not going to fly for most managers) The White’s have a classic dressier look and have huge slabs of leather as the footbed that eventually conform to your foot. They also will last ages and can be resoled when they begin to wear down. The only downside is the cost and possibly wait time, but I think it’s more than worth it for the comfort and longevity.