Degradation products of lignin, a widely available biopolymer, represent the most abundant feedstock for aromatics in nature. In this work, we focused on syringic acid, derived from lignin S-type monolignol, to synthesize different monomers for radical polymerization. The resulting polymers have molecular weight spanning over a wide range, which depends on the monomer, with up to Mn = 1,100,000 g.mol−1 and Đ = 3.0. The novel polymers exhibit a thermal stability higher than 350°C and differentiated glass transition temperatures, ranging from 105 to 120°C. One of the monomers synthesized with a free carboxyl group was able to polymerize in water—instead of organic solvent—and resulted in a water soluble polymer. Monomers from syringic acid offer a unique bio-based alternative to oil-based polystyrene in industry for a wider range of application.