So here is actually every item of clothing I bought, from July 1 2015 to the present day.
July ($264)
Aritzia - 2 white shirts and a dress - $215 (good buy, I wear these all the time)
Merino wool tights - $50 (Well... I wore it skiing a few times. Not that much wear though)
Aug ($100)
Capezio work flats - $100 (good buy, I wear these all the time)
Sep ($1)
A baseball cap - $1 (Dollarama - just needed to keep the sun out of my eyes)
Oct ($6)
Two silk tanks tailor made in China - $80 (good buy, I wear these all the time)
Magic gloves, ear muffs and hat from Dollarama - $6 (They disintegrated over the winter. At least those magic gloves got some good wear)
Nov ($0)
Nothing!
Dec ($20)
Ski socks - $20 (haven't worn these yet)
Dress in Value Village - $15 (not a good buy, I ended up cutting it up anyways)
Windbreaker - $15 (good buy, I wear this all the time)
Nothing!
Nothing!
Bershka leather jacket from a consignment store - $100 (good buy, I wear this all the time, bought as a replacement for a worn out faux leather jacket I had)
10 month total: $521
Not bad!
What I would have done differently - I don't regret purchasing so little clothing at all. In fact, I might have even tried to purchase less, for example not getting the Value Village dress which I ended up cutting up anyways. I might also just have gotten a faux leather jacket in a tan or olive color instead of going for the full on leather jacket, which could have saved me another $40 or $50.
I probably could have gone even less, buying just one white shirt from Aritzia and not getting the dress. Ultimately I could have saved myself another $170 off this year's purchases.
A great, carefully selected year.