Kate M.W. ~ Despite the fact that I’m a strong advocate for flats, sometimes a pair of, say, suede platform wedge t-strap colour-blocked heels just catches my eye and I’m hooked. Completely practical? Perhaps not. But there’s something about these Darnell Wedges from Jeffrey Campbell that seem both playful and grown-up, appealing both to my inner child and my subtle chic older self. The mix of black, grey, and maroon provide a palette that’s versatile and easy to work with.

Darnell Wedge, Jeffrey Campbell, $175

While I’m going to take my cue from the quietly playful side of these shoes, an all-black ensemble (skinny trousers, an oversized sweater, and giant scarf) with cool shades, your hair pulled back, and a great deep berry lip would be an excellent option. Though by now we’ve established that minimalist isn’t my usual pace. T-straps or anything remotely resembling a Mary-Jane always drum up memories of years spent in a school uniform, so I let that guide the foundation inspiration…but not quite the point where you’re channeling your inner Gossip Girl. A pleated skirt and a classic toggle coat may evoke the prep school vibe, but a basic grey v-neck tee emblazoned with life’s necessities and a slouchy boyfriend blazer keep things casual.

Coffee, Cupcakes, Wine Tee, Skreened, $25 / Opaque Tights, Commando, $34 / Tessa Skirt, Club Monaco, $69 / Toggle Coat in Wool-Cashmere w/Thinsulate, J.Crew, $400 / Ruched Sleeve Boyfriend Blazer, Michael Kors, $110

Now it’s all things in moderation, balancing crisp preppy and casual nonchalance. Classic comes courtesy of a dusting of pearls, interspersed along a fine gold chain or set in claws. Or perhaps a touch of sparkle and glitz to off-set a tucked in tee with an ornate playful belt? Regardless of the rest fall’s chill requires something cozy. A thick grey knit infinity scarf would blend in, or if you’re feeling indulgent, a dose of faux fur could be tastefully employed.

Charcoal Infinity Scarf, Tinley Road, $34 / Faux Fur Infinity Scarf, Juicy Couture, $88 / Intertwined Chain Belt, Zara, $30 / Talon Orb Studs, House of Harlow, $55 / Talon Orb Ring, House of Harlow, $50 / Pearl Station Necklace, Wendy Mink, $130

This is the kind of ensemble that you could pair with classic black heels or flats and call it a day. And yet when done up with all the details, it could transition easily between a creative work environment and cocktails. It’s everything with a twist in the details whether it’s great shoes, a t-shirt with a sense of humour, or pearls set in talons.

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