Not every movie star shaped their lips this way, but this was a very popular lipstick style in the late 1930s and into the 1940s. You can tell in these images where the curve of the real upper lip ends and bends into the skin above where the highlight as that looks like a line.
What you are trying to achieve with this look is that the shape of the upper lip mimics and is just as plump as the lower lip. The curve that begins at the low point of cupids bow and rounds out to the outer corner like the top of a heart, as opposed to the gradual decline of a natural lip shape.
Put a foundation and powder on your lips and around first. Then use a lip liner to draw. It makes getting the shape easier and the waxiness of the pencil fills in fine lines to keep your lipstick from bleeding out. Then apply the lipstick.
Or better yet, discover the joy of long wear lipstick. I shared my favorites and the favorites of readers in this post about Red Longwear Lipsticks.
Tip: If you get your outline wrong, mineral oil or 70% Isopropyl alcohol will dissolve the strong red pigment away. Just dip a reusable Q-tip (always trying to reduce waste) in the solution you choose and wipe away the mistake.
Tip 2: Beware of the gloss. If you do not like the feel of longwear lipstick or think your lips feel too dry, use the gloss that comes with the lipstick or check with the manufacturer for guidance on what gloss to use. The wrong gloss can either feel like sandpaper or make the lipstick gooey and fallible.