I've lost count of how many times folks have asked my opinion on what I feel are the best vintage looking, least expensive pair of Engineer Boots and my answer is almost always the Chippewa 27899 or 97866 (do yourself a favor and don't bother with their new "Archival" line).
The best looking pair of 97866's (soft toe) in recent times come from none other than Takeshi Okuyma himself. These boots can be obtained new for about $125 at auction ... even sub-$100 in certain cases (about $145 with free shipping on Amazon). Takeshi took these budget-friendly, yet classic looking boots and gave them a 1940's / 1950's look many would pay top dollar for. The best part is that you'd be in it for about $350. This amazing deal comes with a single mid-sole, #705 Vibram half-sole and heels and a set of his custom buckles, not to mention his amazing attention to detail and craftsmanship.
The original 1940's pair on the right/inset have leather soles, which would save you a few bucks with Takeshi that you can use toward an extra lift to match the stacked Woodsman heel of the original. If you've read enough of my blog, then you'd know the original pair could easily go for $2k ... $2.5k on a good day and closer to three on a great day. Pay ten times less with Takeshi.
Want the waxy shine of the original? Give it a good ol' spit shine. This isn't just for the budget-minded, but also a fan of Engineer Boots in general.
Hukurokuju Boot Repair Shop
Taitoku, Tokyo 111-0021