Im in the same boat. Id really like a pair of alden shells but there are none around in my size. I just cant seem to pull the trigger on any alternative.
One suggestion from some earlier posts you might consider is the Jcrew Redwing. Looks like a nice boot but as i get towards 42, i think i may need something a bit more age appropriate.
I saw those and they looked like a classic looking boot that could be worn by any guy from say 16 to 96. So what would be a more 'age appropriate' boot look like for a guy over 42? Just curious.