Sportster Debbie Boots in Brown

Given my propensity toward retro rebel culture and wearing pretty much nothing but boots myself, it was clear-like, presto!-from the moment we writers opened up the shoebox at one of our daily brainstorm meetings that this pair of boots would be my special project. With their buckled straps wrapping around the ankle, they reminded me of the engineer boots that motorcyclists wear. And when I think of motorcyclists, I think of one of my favorite biker flicks, The Loveless. It's a tale about a 1950's group of bikers heading south to the races in Daytona, and the gang includes a tough-as-nails tag-along they call "Sportster Debbie." I can imagine her donning these brown, leather-like, round-toe boots and hopping on the back of her daddy-o's Harley. You don't have to ride a cycle to wear these, though. For a biker-chic look that's totally cool for just kicking around the city on a shopping excursion, you could tuck a pair of skinnies into the top of these heeled boots and rev up the look with a bomber jacket. Take this style full-throttle by accessorizing with some big hooped earrings and a boldly colored scarf, then gear up for an urban adventure that's totally jake!  -Richard, Fashion Writer