Now that the weather’s starting to get chilly, what’s your favorite outfit to wear out for a night on the town?

Thanks to finally acquiring a fake ID I’ve started going downtown and hitting up the bars, and due to actually leaving my room for something other than class or the gym I’ve began dressing nicer than I used to. Currently I’ve upgraded from my sweatpants and hoodie to some chinos and a slim-fitting OCBD with some Air Maxes, but I’m still looking for more outfits. Some items I’m interested in acquiring are a nice sweater (1/4 zip as well) and some heavier long sleeve shirts (like flannel).

One item I love are flannel jeans, but the pair I have just don’t look good. I wear them if I’m going to the store or just lounging about, but they’re way too loose to wear downtown. Are there any brands that make flannel jeans that look good?

I’ve ordered some chukka boots and a flannel shirt which are on their way, and I’m just looking for some inspiration as to what else I can get. I’ve also never worn jeans, and I’m planning on heading to the mall next weekend to try a bunch of different brands on and see what fits well.