September is always a strange month for dressing. Generally, it’s cool in the morning, hot during the day, and cold at night. This weird weather creates a struggle to come up with an outfit that caters to all the different temperatures we face in one day. September is also the month that immediately creates a divide between those who believe it is still summer, and those who believe it is officially fall.

Just the other day, I was walking around in shorts and sandals, when I passed a woman wearing a full length North Face coat and UGG boots. It was a day on the chillier side, but it was nowhere near negative, or even single, digits.

The other dilemma is figuring out how to transition your wardrobe to incorporate fall trends when it’s still too warm for heavy pieces. This is exactly why I think these Rag & Bone jeans from Aritzia are so brilliant. They’ve got a tweed print (fall) but on a cotton jean in an amazing aqua blue colour (summer).

What I Wore: Sandro jacket from TNT, white t-shirt from Nowhereland, crystal necklace by Wild Moon, Rag & Bone jeans from Aritzia, shoes by Aldo Rise.

Gracie Carroll is a Toronto-based freelance writer whose work has appeared in ELLE UK, ELLEcanada.com, Plaid magazine and FILLER magazine. Keep up with her daily blog at www.graciecarroll.com.