When I moved recently, I was kind of stunned by how much clothing I had. I should know, obviously, but it’s amazing how much I had tucked away in drawers, under the bed and in the back of the closet. It got me thinking about what to keep and re-style, sell, share and donate. I’ll be posting more about this (I have a LOT of clothes!) so I’m starting with one of my signature looks (a printed skirt). 

Photo by Phillip Chin


One of my favourite looks is a pencil skirt in a vibrant pattern. I have quite a few but I was always wearing them the same old way with a black sweater. In order for something to win a place in my limited closet space, I have to be able to style it at least three very different ways. This skirt by Peter Pilotto is an old favourite. Style tip: Pick a bright colour within the print and repeat that in a sweater or scarf. I did that with a JCrew sweater (there’s little hits of purple in the pattern) and classic muffler. I love how a jean jacket dresses it down but then knee-high boots by Stuart Weitzman give it a street chic sense. My navy topper (so much nicer than one in black) is by Vince. And come to think of it my grey Theory coat would be perfect too!

Look 2: I dressed up the skirt with a black cashmere sweater and leather jacket by 3.1 Phillip Lim. My signature accessories make all the difference – I wear my Vera Wang necklace (a mix of clear stones, tulle and leather) and Chloe boots all the time. 

Look 3: And then I dressed the skirt down with a Rag & Bone sweater and my old faithful Gap jean jacket and Prada motorcycle boots. 

So here’s my plan for the next few weeks: I’ll be going through my wardrobe (clothes, handbags, shoes, accessories – everything!) and looking at it all with a critical eye. Do I keep, sell, share or donate each piece?

KEEP: Can I style it three ways? Stay tuned for selfies. I’m always thrilled when I fall back in love with a piece like my Peter Pilotto skirt. Style tip: Keep those selfies in a file on your phone as a handy shopping guide. When I look for new special pieces, I want to be sure that they fit my wardrobe.

SELL: I’ll wear a different piece every day. If I keep fussing with it or just feel uncomfortable, then out it goes. I use consignment stores such as The Style Heiress in Toronto. (My friend Amy runs it and she has amazing styling savvy.) These pieces are generally designer brands,  lightly worn, and usually an impulse purchase.

SHARE: I trade pieces with my family – my university age niece is always happy to get a donation. I love how she styles things so differently from me.

DONATE: And for the items my family can’t use, I also look for local organizations that can benefit, including the Salvation Army. 

Stay tuned! I know that this process is going to cut down on clutter, simplify my life and help me focus on the looks that are truly me.