Dress down a matching suit set in an unexpected hue, with a pair of knee-high leather boots, and you’ve got an edgy twist to an otherwise traditional outfit. Model Aweng Chuol tucks the bottoms of the pants into the boots for a fashionably frumpy look–distressed equestrian style. This look really emphasizes the dual nature of style, in this case, the thin divide between preppy elegance and street-edged trend. To further shake things up, opt for a cropped collared Oxford – it’s just the right amount of buttoned-up edge. This look comes just in time for autumn when the weather gets cold enough for a jacket but isn’t too cold to shy away from some midriff.