We report on a nine-month monitoring campaign of the blazar PG 1553+113, relying on three observations carried out in 2025 with the Imaging X-ray Polarimetry Explorer (IXPE) and supported by multiwavelength facilities. The source displayed pronounced variability across the electromagnetic spectrum, with X-ray flux changes by up to a factor of ∼5 and complex evolution of the optical polarization properties, including one of the largest (exceeding 150°) and fastest rotations in the electric vector position angle (EVPA) ever recorded. This swing of the EVPA was also accompanied by a temporary drop of the optical polarization degree to nearly zero. Significant X-ray polarization was observed during the third IXPE pointing, with a polarization degree ΠX  = (18.4 ± 5.8)% and ΨX  =  74° ± 9° in the 2–8 keV band, while only upper limits were obtained in the first two epochs. The optical data show that the second IXPE observation occurred shortly after a dramatic optical polarization event characterized by a rapid EVPA swing and strong depolarization. Two possible scenarios may explain the broadband polarimetric behavior: (i) the superposition of two emitting regions with nearly orthogonal magnetic field configurations and variable relative contributions, and (ii) the interaction of a single emitting region with a shock that temporarily reorders the magnetic field. In both cases, the data support a picture in which the X-ray and optical emissions arise from closely related but not strictly cospatial regions within a dynamically evolving, magnetically structured jet.