Gary Graham is the kind of guy who would probably make a killing on Jeopardy. A history buff and autodidact, his mood board each season is chock-full of obscure references. For Fall, he was inspired by the Manchester International Theater Festival he attended in July, ancient Iranian wrestling tunics, and WWI naval "dazzle" camouflage. That's quite the combination, but it fit Graham's magpie aesthetic, which emphasizes convertibility and ample layering.

At a preview in Graham's downtown Manhattan store, he piled up a vintage quilt-print dress with fine-gauge sweaters and a deconstructed army vest, then completed the look with a Dickensian wool topper. Styled in a more realistic, pared-down manner, the pieces here would still stand out—particularly the outerwear. The burnished cardinal fingertip-length coat evoked, as the designer put it, a sense of "leftover royalty," while a safety orange padded vest with a split-zip hood added a refreshing touch of sportiness. Graham's clothes aren't for everyone, but aspiring female dandies ought to fancy his unique brand of awkward elegance.