This is the sweet spot of fall dressing. The days are cool, the evenings are getting downright chilly and you can finally start layering without having to fully bundle up. Which brings us to one of the most useful pieces a guy can own: the shirt jacket. Heavier than your typical button-down but less cumbersome than a proper coat, it’s the sort of thing you can throw on without a second thought and immediately look more put together. There’s something appealing about a piece that does double duty, right?

For this outfit, we’re building around Wills’ modern wool overshirt, a handsome, understated take on the style that brings some welcome texture to an otherwise simple look. Wear it open over a substantial dark thermal or a lightweight knit, then add a pair of relaxed trousers or faded jeans for an easy contrast. Down below, some lean boots provide just enough polish without making the outfit feel too precious. Finish with a sturdy leather bag and a watch cap in a complimentary color. It’s the kind of fit that works for an afternoon running around town, a casual dinner or a spontaneous weekend getaway. And when winter eventually shows up, that same overshirt will slip comfortably beneath a heavier coat.