9. The Denim-on-Denim Canadian Tuxedo
Denim is the ultimate transitional fabric because of its durability, wind resistance, and effortless cool factor. Update the classic Canadian tuxedo for the changing seasons by pairing a structured denim button-down shirt with matching straight-leg jeans. Keep the look elevated by choosing matching washes—either a deep indigo or a soft, vintage mid-blue. Layer a lightweight trench or a tailored wool coat over the top for extra warmth, and break up the denim with a sleek leather belt and pointed-toe boots to add a touch of sophistication.