Climb up onto the roof then measure the width and length of each plane of the roof with a measuring tape. Note that on a gable roof there are two planes -- one on each side of the roof. Measure the width and length of each side -- do not assume each side of the roof is the same size.
Multiply the width and length measurements of each plane to determine the square footage of each section.
Add all of the square footage calculations together to get the total square footage of the surface of the roof.
Add 10 percent to the total square footage to compensate for waste and trimming at the roof edges.
Divide the total square footage of the roof -- with the 10 percent added -- by 100. Note that 100 square feet equals one square of roofing material.