9. Denim on Denim with a Tailored Twist

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The Canadian tuxedo has undergone a modern revival, and it is incredibly chic when styled with intention. For midsize frames, the key to denim on denim is playing with different washes or ensuring the fits are perfectly tailored. Try pairing high-waisted, dark-wash straight-leg jeans with a slightly lighter wash, structured denim shirt. Fully tuck the shirt into the jeans and add a sleek black leather belt to create a clear division. Roll the sleeves up to reveal your wrists, which adds a lightness to the heavy fabric. Layer a tailored wool coat over your shoulders in a camel shade to instantly elevate the denim from casual to highly sophisticated.