Ashlee Simpson at the CosmoGIRL Born to Lead Awards

CosmoGIRL hosted their 2007 Born to Lead Awards at Hearst Tower today, and here’s Ashlee Simpson walking the carpet. It seems like Ashlee has finally hit a stride with a chic yet age-appropriate look. She keeps over-the-knee boots from looking trashy by staying monochromatic and covering up everywhere else. It’s also a great example of how to layer to keep warm as it gets chilly.