Yeah as you know, Summer has ended and Winter is about to be here for a little while. Rather than giving you some random Winter items, I only worked with items displayed in the Asos Wrap Star Section and with the mindset of a Glee Club member.
Thought I would do top to bottom, but with a reindeer hat on, for me that kind of defeats the aim of being smart, casual. But that's just me.

The scarf is a bit long, but should drop nicely with the rest of the outfit.
Cable knit cardigans are popular, because they are chunky in order to fight off the cold and I am personally liking the shirt under the cardigan as well. Nice touch.
Spoke about corduroy jeans before but these are decent and also show the Converse's I would recommend or plimsoles. They only had this type in the ASOS Section:
Now maybe I'm too young or not Paris Fashion Week enough, but I can't see myself wearing these. I don't work with timber nor do I operate bulldozers.
Holler at me.