Stapelia similis, the similar stapelia reflects in its name some close relationships in appearance it has with other Stapelia species. This species may be at the cusp of separation versus merging with one or more of the closely related plants of the genus. Notably S. juttae (also with long pedicels), S. portae-taurinae, S. olivacea and S. pearsonii of the S. kwebensis group have shared features.
S. similis forms clumps of erect stems that taper slightly towards their tips. The stems vary in colour between greyish green and dark purple and in length between 7 cm and 15 cm. They are commonly four-angled, sometimes up to six-angled and covered in fine hairs. Regularly spaced tiny leaves occur along the marginal ridges, but drop off early from young stems (Williamson, 2010; White and Sloane, 1937).