Tretorn Klipporone Boot

If you're on the job or simply looking to add some outdoorsman chic to your wardrobe, take a gander at the Tretorn Klipporone Boot ($145). This high-top boot features nine eye laces, a combination smooth and textured leather upper, textured, grooved rubber sole, two-tone laces, and a reinforced rubber midsole and toe cap. While they might look good at a country cookout or impromptu fishing session, don't expect to roll around midtown without drawing some strange looks.