j_86, fellow Canadian! Hope I can share some insights
I like to buy higher quality, more expensive-ish items (at least compared to my friends, who live at Urban Outfitters). I don't have a lot of money at all but I save and splurge on things that last. I would say my style is a bit on the edgier side, still classic. I keep a minimal colour palette - grey, black, white, neutrals mostly. I like a pop of red occasionally. Some items that get high rotation in my wardrobe:
- Equipment blouses, black, red, and white (love these blouses, sometimes I rub my arms when no one is looking to feel the silk!). I try to wear them on more special occasions (dates, nights out) though since they are dry clean only.
- T by Alex Wang tees are huge staples - black, grey, white (have them in t shirt version in all colours, black longsleeve and black muscle T), hand washing them (or delicate cycle in washer) and laying flat to dry and all have lasted 1-2+ years without damage
they accentuate collarbones really well, if you've got it, flaunt it!
- Men's flannels, button downs - sometimes double as cardigans, look great tucked into skinny jeans
- Skinny jeans in grey and black (i also have some more nice ones that are all a size too small at the moment!), Blank NYC, Rag & Bone, Citizens of Humanity and J Brand are staples. I like Blank if you are looking for a good quality jean at a lower price (can buy online at Shopbop, they also sell them at The Bay). Cheap Mondays are ok too.
- Frye engineer boots, black. Can take a lot of abuse (if you live somewhere snow-ridden like me)
- Joie oxfords. I had them in brown, wore them to holes, tracked them down on Amazon in black! Love them.
- Roots Russian Vamp boots - have in tan and black, provide some fashion to these terrible Canadian winters
- Oversized sweaters, most by Wilfred Free (at Aritzia). All 2+ years old, all get worn frequently, great quality as they are all in great shape! They look nice with faux leather leggings and ankle boots
- All my Sam Edelman booties get a lot of wear - have black and putty coloured ankle boots (slightly resemble the Isabel Marant booties), the black ankle boots with fringe on sides, and taupe ankle boots with a rose gold back zipper. Recommend highly. Great quality for the price, and the neutral coloured ankle boots can take a surprising amount of wear.
- Cashmere beanies from Aritzia, Bop Basics (Shopbop's own brand). I think they look cool (also great for a bad hair day, which for me is most days, lol).
- Love Quotes scarves, nice to top an outfit off in Fall/Winter. Also look good just draped over the neck with a nice shirt and shorts in the summer
- Aritzia utility jacket in olive. Everyone has them here but what can I say, they are cute (and comfy). Good for spring and fall, warmer winter days.
- Daily jewelry - Helen Ficalora initial necklace, MK silver watch, Dannijo and Gorjana rings and snake/skull rings by Michelle Chang.
I guess that's basically my whole wardrobe
I feel like I wear almost the same thing every day in a different colour/combination, but I guess it has become a signature over time and I quite like it. Oh! And to top it all off, I wear glasses a lot, either the Ray-Ban wayfarer or clubmaster style. It helps me maintain my reputation as a huge nerd
(also, excuse this essay of a post, I love fashion, shopping, etc!!)