Human skulls and skeletons are one of the most common elements in the Grim Reaper tattoos, due to the fact that skeletons and skulls have long been associated with death and decay (sometimes Death himself is portrayed as a skeleton).
skull tattoo / raven tattoo

Skull tattoos do represent death, but they usually represent the fleetingness of life. Various Latin maxims and aphorisms: Memento Mori (Remember your mortality, Remember you must die or Remember you will die), Sic Transit Gloria Mundi (Thus passes the glory of the world), Carpe Diem (Seize the day), Ubi sunt...? (Where are...?) or Ubi nunc...? (Where now...?) - both of them are shortened variants of the Ubi sunt qui ante nos fuerunt? Where are those who were before us?) are very often included in the skull tattoo designs; their role is to remind us that Death comes to us all, and for this reason is important to enjoy every moment of life.
skull tattoo / Memento mori tattoo
skull tattoo / flower tattoo

Seize the day or die regretting - a tattoo design which contains flowers (which symbolize brevity and the ephemeral nature of life) and a skull

Memento Mori tattoo / skull tattoo / tattoo on the arm

As a symbol of the certainty of death, skulls are one of the most common symbols used in the Vanitas art
vanitas tattoo

vanitas tattoo
vanitas tattoo
Despite the fact that the skull is often a symbol of mortality, a design which depicts a skull backed by a pair of wings (usually a pair of angelic wings, but this is not mandatory) is rather a positive design with various meanings: resurrection; death is the road to a new form of existence; the death frees one of the burdens of life; the progression of the human soul through the afterlife. Anyway, the winged skull is not always a positive design, having also many negative connotations: danger, death (death which can reach everyone everywhere), lawlessness (very common in the bikers-gang tattoos)

winged skull tattoo
winged skull tattoo
bikers tattoos: winged skull tattoo
The skull is also a symbol of the transitory nature of life and death, and for this reason some designers choose to include a skull into more complex designs which represent the infinite cycle of the life and death.
skull tattoo / flower tattoo
 
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