As an effective method to reduce induced drag and the risk of wake encounter, the winglet has been an essential device and developed into diverse configurations. However, the structures and induced drag, as well as wandering features of the wingtip vortices ( WTVs) generated by these diverse winglet configurations are not well understood. Thus, the WTVs generated by four typical wingtip configurations, namely the rectangular wing with blended/raked/split winglet and without winglet (Model BL/ RA/ SP/NO for short), are investigated in this paper using particle image velocimetry technology. Comparing with an isolated primary wingtip vortex generated by Model NO, multiple vortices are twisted coherently after installing the winglets. In addition, the circulation evolution of WTVs demonstrates that the circulation for Model SP is the largest, while Model RA is the smallest. By tracking the instantaneous vortex center, the vortex wandering behavior is observed. The growth rate of wandering amplitude along with the streamwise location from the quickest to the slowest corresponds to Model SP, Model NO, Model BL, Model RA in sequence, implying that the WTVs generated by model SP exhibit the quickest mitigation. Considering that the induced drag scales as the lift to power 2, the induced drag and lift are estimated based on the wake integration method, and then the form factor λ, defined by [Formula: see text], is calculated to evaluate the aerodynamic performance. Comparing with the result of Model NO, the form factor decreases by 7.99%, 4.80%, and 2.60% for Model RA, Model BL, Model SP, respectively. In sum, Model RA and BL have a smaller induced drag coefficient but decay slower; while Model SP has a larger induced drag coefficient but decays quicker. An important implication of these results is that reducing the strength of WTVs and increasing the growth rate of vortex wandering amplitude can be the mutual requirements for designing new winglets.