Come fall or winter, layering is the easiest strategy to looking sharp, sophisticated, and downright in the know. Every time I layer well, folks ask me where I bought at least one of said layers. I’m not exactly King Cool, or even Prince Pretty Posh, but layering is something of an illusion. If you can master this one skill in dressing well, people assume you could roll up to any event looking like royalty, where by crown or celebrity.
Back in the day, you could get away with a zip-up hoodie and a blazer. To be honest, you still can. The look has something of a timeless yet youthful quality. It’s fun, casual, and provides a smooth operator vibe. It presents a presence without demanding attention. It’s just an eye-catching look that reads as if you’re game of anything.
As I’ve gotten older, however, I have, as one does, leaned more on polo shirts and henleys, both short sleeve henleys and long sleeve henleys, to rock with a super-soft cardigan. Men’s basics are forever the way to go, since they never go out of style, so what changes is what you pair with ‘em. For me, a polo or a henley with a cardigan, whether its focal selling point is looking stylish or feeling comfy, is a powerhouse move, especially around the holidays. A good cardigan-led outfit will get questions, prompts, and compliments from anyone at a holiday party if you strut in rocking this hot-to-trot business.
Otherwise, stick with a lightweight sweatshirt atop your t-shirt and beneath your coat, whether it be bomber or wool, to look especially fly. It’s probably not as hard as you think to be really, really, ridiculously good-looking.
— Jake Kilroy