i've paired down to only 4 Aldens, after buying and selling off a few pairs along the way:
#8 unlined ptb, flex welt, barrie from Alden SF
Snuff suede chukka, flex welt, leydon
Black cordo captoe boot, double leather, barrie from Alden SF
#8 plaint toe boot, commando, plaza from J. Gilbert
i can wear pretty much whatever i want to work, and i find these 4 models give me options in all seasons and a chance to rotate during the week. i wouldn't mind adding something in cigar somewhere down the road, but i'm pretty content with my little collection.