Start at the bottom of the roof and roll out the 30-pound asphalt roofing felt. Overlap each row by about 2 inches, and secure the felt with 1-and-1/4-inch galvanized roofing nails. While installing shingle roofing can be challenging and dangerous, understanding the process can help you decide whether to tackle it yourself or hire a professional. How to install shingles on a shed roof is challenging, let alone on the roof of your home. This guide will walk you through the steps of installing roof shingles, from preparation to completion. In the video above, This Old House expert Tom Silva demonstrates the proper techniques for shingling a roof.