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What chukka boots does the styleforum groupthink approve of?
Bargain basement = Clarks
Sneaker like = Common Projects
"midpriced" = Churchs, Trickers (my preferred), APC, Alden, Filippa K, Sanders, and so on.
OMG expensive = John Lobb, St. Crispins
Mid priced = Paraboot, At $400, they don't come cheap but they are a lifetime investment.