I never bought any expensive boots in my lifetime. When I bought the Chippewas I got them new from a guy that worked for the power company. They bought him a new pair every yearI gave up on redwing boots years ago. Had 2 pairs of American made loggers, with composite toe and metatarsal guard. (Work requirement at the time.) Every other year I'd send them back in to get the foot bed and sole redone. Think it was around $90.00. Came back with a new foot bed, sole, polished up and a set of laces. Went back in one day to send one of them off, and the manager said they wouldn't be able to send them back, because that model boot was discontinued. Fought with him a little, then left. Sent redwing an email, and got the same response. They offer that service for current model boots only. I wouldn't have been so up set, but they were over $500.00 for each pair, and the boots were in good shape other wise. Haven't given them a red cent since. Got a set of chippewa boots after that, got about 3 years out of them before the soles needed redone. Local cobbler said $125.00 for new soles. Just wasn't worth it for a ~$200.00 boot. Ended up getting Georgia boot to replace the chippewas.
I bought the 3 pair that he was selling. I sold one pair which paid for all three pairs. At 5'8" the Chippewas make me feel tall,. Hopefully I can get these broken in eventually. I hate to soften up the leather because then it makes it easier to wear. My normal work boots are Wolverine or Timberland brand. They normally do not require any break in time.