The retrosynthetic design and synthesis of three unprecedented doubly N-confused porphyrinoids with tunable aromaticity are reported. The controlled modification of the type of oxidant (chloranil vs. DDQ) led to the isolation of cross-conjugated doubly N-confused porphyrinoid 7 (upon chloranil oxidation) and Hϋckel aromatic porphyrinoid 8, while DDQ oxidation led to the [16]π Hϋckel-antiaromatic porphyrinoid 9. All three hybrid N-confused porphyrinoids 7-9 have been thoroughly characterized …