(1) Frye Marco Chukka The sixties-inspired Marco looks well traveled, but that's on purpose; this full-grain leather is as wear-resistant as it gets. $198; thefryecompany.com

(2) Børn Hemlock Hand-sewn with a leather upper and lining and a rubber outsole, the Hemlock delivers more flexibility than your average boot. $124; bornshoes.com

(3) Clarks Unstructured Un.Sheridan Clarks' proprietary, comfort-driven Air Circulation System keeps the Un.Sheridan dress shoe from getting clammy. $135; clarksusa.com

(4) Johnston & Murphy Kaylor Strap Boot This one may take a bigger bite out of your wallet, but the leather lining and removable footbed, all wrapped neatly in Italian calf, give you a higher degree of dressability. $250; johnstonmurphy.com

(5) Rockport Brombeck Part of Rockport's Fine Vintage line, the Brombeck has a nicely distressed look right out of the box, and the supple pigskin lining just feels good. $110; rockport.com

(6) Ecco Berlin Gore-Tex Calf leather and waterproof-breathable Gore-Tex make Ecco's Berlin Gore-Tex boot ready for either dress codes or foul weather. $200; eccousa.com

(7) Merrell Orion Active-footwear company Merrell ups the ante this fall with its business-meets-casual Orion shoe, with top-grain leather, supple pigskin lining, and antimicrobial treatment. $100; merrell.com

(8) Timberland New Labourer Chukka Timberland found inspiration in the Depression era for its industrial-style New Labourer, with hand-finished burnished suede. $300; timberlandbootcompany.com