When it comes to fashion, I believe there are no rules. Almost anything can work if you have the right attitude. That said, sometimes an outfit can look out of proportion, lazy, or inappropriate for the event you're attending. Unfortunately my favourite style of jean—the boyfriend jean—can easily fall into any of these categories. Here are a couple of fail safe outfits that include the sexy androgynous denim, whether you're dressing for work or play. 1. Professional: Look for a slouchy dark denim without holes and pair it with a silky blouse (a bit of femininity to balance out the masculine edge of the jean), cropped bouclé jacket and chunky jewellery. Heels are an absolute must. Sabine bouclé moto jacket, $80, piperlime.gap.com. Boyfriend jeans, $80, gapcanada.ca. J.Crew necklace, $175, net-a-porter.com. Heels, $80, aldoshoes.com. Blouse, $55, loft.com. 2. Casual: It's a lot easier to get away with a grungy wash or rips on the weekends. Try pairing your worn out boyfriend jeans with a collared shirt, sweatshirt and sneakers. Wear slouchy socks if your ankles get cold. Shirt, $30, reitmans.com. NSF boyfriend jeans, $185, shopbop.com. Waffle knit toque, $10, joefresh.com. Top, $50, canada.frenchconnection.com. Vans sneakers, $69, revolveclothing.com.