If you're one of the "zero drop" guys then either have a cobbler take off all the stacked leather of the heel and replace the lift, or get some driving mocs/boat shoes/fashion forward sneaker-oxfords.
If the squeaking is from the sole or heel, no. It may work itself out in time.
Shoes and boots will give and break in as much as they need to, in mostly all areas except for what's directly stitched to the sole. Those ankle bone...
Is anyone else in love with the old Allen Edmonds Windsor monk strap boot? I wish they'd bring it back.
AE has no strap boot offerings, and there are no currently produced boots of this style in the AE price range.
I found a pair of Florsheim Royal Imperial scotchgrain PTBs in 9 E, which have pictures and are available in my B&S thread.
I also found a pair of FRI burgundy cordovan longwings, which are a present for my Dad because I love him and...