1. Not to be a judger or anything, but if you're gonna dress all pseudo-lady, leave last year's ski jacket out of the outerwear equation. This wool number by CinCyn ($685, Willow Grant , 960 Queen West, 416-533-7553) is a nice solution.
2. Available in a selection of vibrant shades, this tailored, poly-quilted puffa ($79.99, Winners , 444 Yonge, 416-598-8800, and others) is like a duvet with arms - great for those dark winter mornings when getting out of bed is a nightmare.
3. If you're likely to spill a latte on your person or fall into a puddle, this piece of winter-white genius from Montreal dynamos Mackage ($650, Studio Deluxe , 793 Queen West, 416-603-3704) may not be suited to your lifestyle.
4. Work those adolescent good looks - even if you're no longer teenaged - in this fuchsia-lined bomber jacket by Hooch ($194, D lovely , 202 Augusta, 416-593-9095). Pair it with an exposed hip bone, and they'll never know you're mutton dressed as lamb.
5. Thanks to Teenflo's classic tailoring, this houndstooth tweed coat ($425, Finishing Touches , 3281 Yonge, 416-482-9034) boasts vintage good looks, minus the musty second-hand fragrance that typically comes with.