AE has a number of lasts, each will fit your foot a little differently. From experience, the shoes will stretch a bit and the insole will mold to your foot; However, the edges of the insole, being welted, will not. The shoes should be a little snug when new, but your heel should not be pressed against the shoe. Neither, however, should your heel slip out when you walk. In theory, I believe each shoe from the same last should fit the same, although I find the Park Avenue to run smaller than the Strand.
I wear my black Strands with jeans and slacks, but I feel they are a bit too dressy at times. I wish I had bought them in walnut.
Being on the verge of 4E, I have had the trouble of facing heel slip or minor insole-edge toughness from one half-step to another. My third pair, arriving next week will be 10.5eee should eliminate that edge soreness, but a boot, which will hopefully help with the slippage.
I wear my walnut strands with jeans when I wear a blazer and dress shirt with jeans. For the most part I only wear my strands on special occasions as they are my nicest pair of shoes I own.
Also, I generally purchase the same size shoe regardless of the last. I own 3 pairs of AE to date, and for the most part that rule has worked out. The exception is with the Malvern which are a bit loos so I wear a thicker dress sock.