As I reflect on my wardrobe of last year I think I need to up the footwear game for 2014 and step away from the pleather leggings. I know you’re a classic dresser but do you have any new years resolutions in fashion?
–Bronwyn

Dear Bronwyn:

I find your question to be a double-barreled one, and it’s causing me to reflect on the true meaning of “fashion”. There are certainly all kinds of practical resolutions that I make each year, when I’ve not only taken stock of the stash that’s in my wardrobe, but also of my stylish comings and goings. Exactly what pieces have served me well? How truly satisfied was I with the options I had? What garments and accessories really made me feel great, and which did I feel uncomfortable in? What were those items that victimized me? And what types of things did I really long for, but never managed to purchase? Then there are also the big philosophical questions about fashion and the role that it plays in our lives. Is it really fashion that makes my soul sing? Can I justify all that I spend on wardrobe? Do I spend too much time worrying about the whole question of what to wear?

First, let’s deal with some practical points. For 2014 I resolve not to purchase shoes that absolutely kill me feet. A little discomfort in high fashion footwear is sometimes de rigueur –just part of the territory. And I’m willing to bite the bullet just a bit once in a while. But the last pair of “uncomfy” stiletto pumps I purchased have been the bane of my existence every time I wear them, and I’ve decided life’s just too short to put up with that kind of nonsense. I’ve also resolved to invest in a couple more high quality basics that I can ride with all year—pieces like the Wolford turtlenecks I so love, that I see as investment pieces. I’m finally going to get myself a great alterationist and re-visit some of the older garments that I can’t bear to part with. Perhaps I can pump new life into them if do some nipping and tucking in all the right places. Another resolution, in the vein of getting to the gym more often? Shaping up in the workout wear department! It’s hard enough to drag myself out of my cozy bed at dawn, and go into the freezing cold for those early morning trips to the gym.   I resolve to get myself some fantastic new workout clothes that will help give me incentive to spring into action. And one more thing: As much as I’m addicted to my little black dresses—and I have many wonderful ones—I’m going to try give a nod to more colour when it comes to nighttime dressing. Of course, black will always remain my go-to staple, especially on days when I’m feeling fat! (The slimming effect of black is always a godsend.) But it seems that every time I go for colour in evening garb, the compliments start flying. So I’m going to go for a couple of colourful new cocktail dresses to throw into my chic black mix, for those nights when I want to make a punchier statement.

On the philosophical front, I resolve to get into a positive mindset for 2014—on every front, wardrobe included. I’m going to stop feeling as though I have nothing to wear when I know darn well my cup runneth over. I’m going to think five times before splurging on some sensational piece (I now think about three times). I can’t say I’ve ever really regretted any of those big price ticket things I’ve gone for, but there are so many other fantastic things to spend my hard earned money on. And most importantly I’m going to continue working on feeling comfortable in my own skin, keep trying to always put my best foot forward, and constantly remind myself that while fashion can indeed make us feel empowered, real empowerment comes from the confident fashion choices we make—not the actual fashion itself. Happy New Year!