Enantiomer separations have been one of the most important and, simultaneously, one of the most difficult to accomplish analytical (and technological) tasks, present at the top of separation scientists’ agenda since the early sixties of the last century. Awareness of their importance has been awakened by an infamous case of the racemic drug thalidomide, a widely advertised sedative drug which had unexpected teratogenic activity in pregnant women that resulted in thousands of ‘flipper babies’ born in the late fifties and the early sixties in many countries around the world. Since that time, separation scientists have developed numerous methods for enantiomer separation, basically by use of gas chromatography (GC), high-performance liquid chromatography (HPLC), and capillary electrophoresis (CE). In this respect, planar chromatography has remained to a large extent an undervalued enantiomer separation technique, despite separation performance sufficient to separate a pair of enantiomers. The large number of GC, HPLC, and CE enantiomer separation strategies and methods developed are evidence that — once confronted with this particular and no doubt very important challenge — instrumental chromatographic techniques have lost if not face, then, to a large extent, their reputation as robust, universal, and efficient separation tools. In these circumstances, planar chromatography on silica gel seems a very promising and tempting alternative, basically because of the advantageous properties of microcrystalline silica gel and the 2D effective diffusion available only in planar chromatographic mode. Enhancement of the enantiomer separating power of the silica gel by simple mechanical impregnation with a properly chosen chiral selector, and additional coupling of this with efficient instrumental detection (e.g. densitometric, DAD, or mass spectrometric) can yield in a simple, robust, and universal tool for separation of enantiomers comparable with the long-established chromatographic enantiomer-separation techniques. In this mini review, favourable preconditions for silica-gel-based planar chromatographic separation of enantiomers which can elevate planar chromatography to the status of leading tool for separation of enantiomers are discussed. Further improvements which can enhance the enantiomer separation performance of chiral planar chromatography are also indicated.