Today’s designer men’s jeans reflect the dynamism and epochal flexibility of the endlessly enduring staple. One of the primeval pieces of ‘the American look’, the garment inhabits a vast and at-times contradictory range of signifiers, from simplicity to complexity, utilitiarianism to denim snob excess, and modesty to sexiness. Premium raw denims, Japanese selvedge, and artisanal washes present an endlessly complex constellation of wearing options. Clean minimal options thrive on uniformity of hue. Tapered and cropped looks find their appeal in clean geometry and a nod to the more formal aura of trouser tailoring. Distressed variants embrace wear and tear and the appeal of the worn-in and strategically worn-through, achieving looks from the grunge to the avant-garde. Meanwhile, the recent uptick in interest concerning workwear has brought select, seemingly inextinguishable heritage silhouettes and brands back to the mainstream yet again. Up-cycled reclaimed vintage pieces bear both a sense of thrift-store historicity with the ineffable refinement of auteur revision.