Throughout his career, Simons garnered critical acclaim for his collections which blended pop culture and sleek design to impressive result. He was, in particular, inspired by youth culture, choosing to focus much of his early work around both American college boys and English schoolboys. He also took a leap into the mainstream with his 1998 'Radioactivity' collection, in which legendary German electro band Kraftwerk walked the runway for him in outfits that they would soon don for the cover of their iconic 'The Man Machine' cover.
Simons succeeded in using mainstream culture to his advantage;his collections themselves were always extremely well-tailored and usually featured an absence of intricate pattern. Heavy block colours dominated Simons' runways, and his clothing was often imbued with small messages that had a tendency to reflect upon society at the time. The way in which he was most successful is that he opened up the world of menswear to a more interesting aesthetic - the models that he used were often waifish with razor-sharp cheekbones, a look which contrasted with the hyper-masculine look that men favoured at the time. His use of androgyny and oversized tailoring set him aside from his contemporaries and made him one of the first truly groundbreaking menswear designers of his time.