I have a pair of Edward Green Chelseas for sale. These are timeless classics and are exceptionally well made. Goodyear welted with a closed channel outsole.
Premium black calf on the 202 last. Size 8.5/9E . These shoes were worn for 5 hours. Asking $700 $650 shipped CONUS.
For flannel I'd take a look at fox's selections
For hopsack I'd look at Smith Woolens gilt edge (plenty of other options at Harrison's)
For fresco I'd do Minnis. Other frescos are also nice, but I think Minnis would work best for a navy DB.