While a final acceptable answer for the wood-chucking dilemma is yet to be found, the fruit of the collaboration between J.Crew and shoe-classic Sperry Top-Siders® is by no means unsatisfactory.
The J.Crew Original nubuck chukka Sperry Top-Siders ® boots are a mix between a chukka boot, defined by Princeton's online dictionary as a shoe that comes up to the ankle, laced through two or three pairs of eyelets and often made of suede and a classical boat shoe.
These boots, vaguely reminiscent of the 70s, are definitely a collector's item. Whilst J.Crew originally sold them in both Chocolate and Espresso, only the latter is still in stock and can be purchased online at Jcrew.com
Lined with cotton chambray, these boots can be worn with or without socks and paired with a straight-leg(Dur) dark denim jean in order to maintain that preppy look into the colder seasons.