I've never bought expensive boots in my life and I've recently been looking at the Wolverine 1000 Mile boots. I've never heard of Oak Street. How do these compare?
KailecI personally own both and the OSB are far superior boots. They both use Horween Chromexcel leather but the overall quality of the boots are much better. Also, from an aesthetic standpoint the toe box is not as high as the 1000 mile boot.
KailecThey're definitely comparable, although I'd give the edge to OSB. It mostly comes down to what style you prefer. Like others have said, OSB has a lower toe box, which makes it look a bit less bulky. Hard to go wrong with either, but at this price I'd say the OSB option is the best, dollar for dollar.
IanAndersonWith the "strength" of the Canadian dollar right now these would cost me over $500 all in (with duties I know I'll be hit with). I can get the 1000 mile right now $361 roughly. Is it worth the price difference?
ilumoI personally wear a 8.5 in 1000 mile and 9 in OSB trench boots. They say that they are true to size with whatever you measure on a brannock device., I happen to measure a 9.5 and the 9's are perfect for me.
KailecThe 1000 mile isn't worth $361. These might not be worth $500 either. The Exchange rate is kind of biting you, the quality control on 1000 miles is not the best. If I were you and willing to spend that much, I would contact Dayton Boots in Canada (better for your Canadian Dollar) and do a Service Boot make-up. Much better quality than OSB or Wolverine, and more aesthetically pleasing, as well. THAT would be ~$500 CAD well spent.
KailecThese boots are made in the USA from American components. Per NAFTA, you should not be charged duties. You may get dinged for taxes, but not duties.