5. Kenneth Cole calls it the Rocky Mountain, but with distressed Italian calfskin and an angled side zipper, this boot leans more toward fine dining than fourteeners. $355; www.kennethcole.com 6. In addition to being street sleek and comfortable (with a cork insole), Simple's Postman Boot is also eco-friendly (at least for a leather shoe): It's made with nontoxic, water-based glue and shipped in minimal packaging. $100; www.simpleshoes.com 7. Part Transformer, part classic Timberland boot, the oiled and distressed Speke Moc Toe Chukka has a removable SmartComfort multidensity chassis, which can be adjusted for various levels of support. $100; www.timberland.com 8. If one shoe could look good on both LeBron James and Johnny Depp, Dry-Shod's basketball-inspired Cannon, made with handcrafted Italian leather, is it. $190; www.dryshodfootwear.com