Reported are syntheses of several new monomer precursors of cathodically coloring conducting polymers (CPs), based on a propylene dioxythiophene skeleton. These are shown to yield CPs—both as homopolymers and as copolymers—that are nearly “perfectly” matched electrochemically and electrochromically with a set of anodically coloring poly(aromatic amines), for use in dual-polymer electrochromic lenses. Resulting dual-polymer electrochromic lenses display very high light/dark contrast (typically up to 70/7% or 50/0.5% Transmission (integrated over visible spectrum, vs. air reference), Haze < 2%, very high cyclability (> 10 K cycles), multiyear shelf life, appealing transparent to dark-blue-black transition, and excellent optical memory. Dramatic lowering of switching time, from 8 to < 1 s, is demonstrated using unique applied-potential algorithm resident on inexpensive Microcontroller chip. Working, practical dual-polymer electrochromic spectacles are demonstrated with electrochromic lenses retrofitted to spectacles meeting ANSI Z87.1, GL-PD 10–12 (U.S. military) specifications. These incorporate photosensor, rechargeable Li battery, Microcontroller, allow for automated operation. Ab-initio-design spectacles, also conforming to above specifications, are also demonstrated, with components seamlessly hidden within frame. To the best of our knowledge, the electrochromic lenses and sunglasses reported herein represent the best visible-region electrochromic performance for dual-polymer CP electrochromic systems to date and the first practical implementation in working sunglasses. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 41043.