A compendium of pnictogen and chalcogen substituted boron heterocycles were assessed for their aromatic character by first principles density functional theory. Group-15 and Group-16 elements were placed at the ortho-, meta-, and para-positions of six-membered rings relative to boron to assess their impact on the aromaticity of the unsaturated heterocycles. Aromaticity was analyzed by a multidimensional approach using nuclear independent chemical shifts, gauge-including magnetically induced current, as well as natural bond orbital and natural resonance theory analyses. Based on these methods, we observe a general decline of aromaticity in heavier pnictaborines while the chalcogen analogues maintain relatively strong aromatic character. These general trends result from complementary π-π* natural bond order interactions that sustain resonance within the ring of each heterocycle establishing a pattern of cyclic delocalization. Consequently, natural resonance theory displays strong resonance, which is corroborated with the signed modulus of ring current, toroidal vortices of current maps, and elevated average induced current throughout the ring. The 1,3-configurations for pnictaborines and chalcogenaborines are generally more aromatic compared to the 1,2- and 1,4-isomers, which contain π-holes that limit diatropism within the heterocycles. However, an energetic trend favors the 1,2-heterocycles in both groups, with a few exceptions driven in large-part by π-donation of the lone pair on the heteroatom to the pz orbital on the adjacent boron resulting in stabilization. The importance of planarity for high aromaticity is demonstrated, especially in the pnictaborine isomers where pyramidalization at the pnictogen is favored, while bond regularity seems a less important criterion.