This sounds like a fun idea! Here's my pinterest board (actually has 31 pins, but 3 are outerwear).

Like you, I also want to make sure I wear my newly purchased items, as well as several items I've had for a long time that I still like the look of, yet never seem to reach for (ex. my Doc Martens bought in 2015!). I've also noticed that I tend to go for an everyday, ultra-casual formula of tee + hoodie + leggings + sneakers, and I'd like to get out of that habit and look a little bit more put-together, so I chose a lot more jeans/sweaters/boots and less athleisure/loungewear. Unfortunately I live in a colder climate, so I can't experiment too much, but I'm excited to see how this turns out!