A novel auxetic structure-based stiffener for stainless steel–carbon reinforced polymer (CFRP) T-joints with outstanding strength and toughness improvement is proposed. The stiffener was composed of a bulk web and re-entrant structure flange that was 3D printed using a selective laser melting 3D printer. The stiffener was bonded to a CFRP skin, and a pull-off test was performed to evaluate the pull-off strength, stiffness, and toughness of the joint. The results demonstrated that the proposed structure has specific strength and toughness that were 3.4 and 77 times greater than those of the baseline joint, respectively. The improvement in strength was due to the delayed damage initiation caused by the mismatch between the bending stiffness of the bulk web and the stiffener under the first re-entrant structure. However, the damage initiation in the baseline joint was located at the stiffener edge. Moreover, the negative Poisson's ratio of the re-entrant structure arrested the delamination growth after damage initiation, which enhances the toughness of the joint. By optimizing the structure of the stiffener, a joint with 2.66 and 38.2 times larger specific strengths and toughness compared to the baseline joint with the same specific stiffness was achieved.