Double down on denim for an unexpected party look. While the combo tends to veer towards the overly casual—hello, Canadian tuxedo—this power coupling is all about feminine appeal. Both the Anoki and the Pierson are engineered to flatter the figure—the latter with a slimming pencil silhouette and the former with sharp, narrow shoulders and a nipped-in waist. Heels are a no-brainer, but for a shot of nonchalance, we love finishing with croc-embossed loafers.

A great denim skirt is like a great blazer—it’s a secret weapon to elevate the everyday. Pair it with a simple tee or easy knit, for instance, and you’ve still got a look that’s totally pulled together. Try it with our Virke marinière—a lightweight transitional piece that takes you from summer to fall—then add a slouchy boyfriend jacket for an element of off-duty chic. Further the relaxed vibe with sneakers or a low block heel.

Here’s a new take on the VB uniform: instead of jeans, channel your inner Hutton, Birkin and Bessette by pairing the dickey jacket with a streamlined pair of corduroy pants. Keep the texture play going with suede heels, in a neutral hue, for the perfect desk-to-drinks finish. This one’s great for transitional seasons, too—just add a thin turtleneck, like the Cedar, once the temperature drops.