There’s a sweet spot in the season when a heavy coat feels like overkill, but just a T-shirt won't cut it either. This is when layering becomes essential—not just for warmth and comfort, but for style, too. Between fall's cool breezes and winter's creeping chill, it's all about versatility. The right mix of textures and fabrics lets you move through the day without missing a beat—warm in the morning, breathable by afternoon, and polished enough for whatever comes next.

Start with a sturdy foundation. We'd suggest Taylor Stitch's Division shirt, an almost-shirtjacket that pulls double duty as a mid-weight outer layer. The cotton fabric is heavily washed to bring out the depth of the sashiko-woven indigo yarns. Throw that over a textured long-sleeve tee for easy, rugged appeal. Pair them with some modern cargo pants—functional but streamlined—and a set of classic sneakers that keep you light on your feet. From there, layer in cold-weather staples that add both utility and personality. Dressing for right now doesn't have to mean bulk. It's about smart layers, built for transition.