Catering to conservative and anarchic inclinations and endless wearing contexts, the landscape of contemporary designer men’s shirts is indelibly vast. Poplin, twill, and Oxford cloth button shirts appear in contemporary slim fits, boxier ‘dad’ varieties, and swing collared slouchy oversized pieces. Button-concealing plackets and satin trim feature on select garments, variously providing a clean minimalist sheen and a regal contrast that occasionally lapses into delightful pajama-top referencing splendor. Choice of collar radically determines the personality of a piece, with stand collar and open spread collar variants moving away from ritualized formality. Traditional spread and button-down collars supply the means for hosting a tie and, by extension, achieving absolute properness. Deconstructive impulses animate the tailoring choices of some designers, with asymmetric and mismatched material constructions, overlong sleeves, multiple wearing options, and modified collars emerging as notable tropes. Such experimentation expands the contingencies of use for the menswear staple, as variegated avant-garde-isms hint towards the multiplicity of possible, distant mainstream futures.