There are three ways to do this and only one of them puts you on the roof. All three produce the wrong answer unless you apply one multiplier that most people have never heard of.
A roof's area is always larger than the ground it covers, because it slopes. The steeper it is, the bigger the gap. At a 12/12 pitch the roof surface is 41 percent larger than the footprint underneath it. Measure the footprint, forget the multiplier, and you under-order by that much.
From the ground. Measure the building's footprint by walking around the outside, then work out the pitch separately, then multiply. This is the safest method, it needs no ladder, and for a simple gable roof it is accurate enough to order material from. It is also where a laser measure genuinely earns its money, because you can take long runs single handed against a wall.
From satellite imagery or an app. Fast, and fine for a rough quote. The limitation is the same as the ground method plus one more: the software knows the footprint but frequently guesses the pitch, and a guessed pitch propagates straight into the area. Treat the output as a starting figure to check rather than a number to order from.
On the roof. The most accurate, and the one that needs proper fall protection. Measure each plane directly, rake to eave and along the ridge, and no multiplier is needed because you are measuring the actual surface. Worth doing on a complex roof with multiple hips, valleys and dormers, where the ground method starts accumulating assumptions.
Roof pitch is written as rise over run, in inches of rise per 12 inches of horizontal run. A 6/12 roof climbs six inches for every foot across.
The multiplier for any pitch is the square root of the rise squared plus 144, divided by 12. In practice you look it up:
So a 2,000 square foot footprint at 8/12 is 2,000 times 1.202, which is 2,404 square feet of actual roof, or just over 24 squares. Skip that step and you are ordering 20 squares for a 24 square roof. The full multiplier table and worked examples are here.
Honest about this, because roofs are where these tools are both most useful and most frustrating.
They are excellent for the footprint. Long wall runs, single handed, braced against a corner. They are excellent for indirect height, using two readings and the angle between them to get eave or ridge height without a ladder, which is the standard way to derive pitch from the ground. Indirect measurement is covered here.
They struggle in exactly the conditions roofs present. Bright sunlight collapses usable range well below the rated figure, and the red dot becomes invisible on a light coloured roof at forty feet. A green beam helps you place the dot. On long outdoor runs the practical answer on premium units is a camera viewfinder, where you aim with a crosshair on screen rather than hunting for the dot at all.
If you measure roofs regularly, that is the single feature worth paying for. The roofing picks are here.
Nothing on this page is worth a fall. Roof work is among the most common causes of serious injury in construction, and a measurement is never the reason to take a risk you would not otherwise take.
The ground method exists precisely so you do not have to go up. If the roof is steep, wet, frosted, brittle with age, or you do not have proper fall protection and a stable ladder, measure from the ground and accept a slightly less precise number. If it genuinely has to be measured up close and you are not equipped, that is a job for someone who is.
Roof area is not the order quantity. Shingles need extra for the starter course along the eaves, the ridge cap, hip runs, valley cuts and offcuts around penetrations. A simple gable roof carries a modest allowance. A complex roof with several hips, valleys and dormers carries a much larger one.
Ordering shingles is covered separately, because the extras are where roof estimates most often come up short. Metal roofing works on entirely different logic, since panels come in fixed widths and custom lengths rather than being cut from area.
For the overview, our main laser measure guide covers the picks and the reasoning in one place.