I am planning clothes for an upcoming holiday to Chicago (5 days). I will probably travel in my Hush harems and a couple of layered tops, with trainers.
I was thinking of the grey puff sleeve dress with biker boots. If it is very cold I can wear thermal tights and a thermal long sleeve top under it, and if it is just cool I can wear with regular opaques.
Then, 2 wide jersey tops and either skinny black Cos trousers or the leopard leggings. Also with biker boots.
Then the last outfit could be a pair of my gap girlfriend jeans with my (new) favourite Cos knitted jumper and white trainers.
www.cosstores.com/en_eur/women/womenswear/tops/knitted-tops/product.textured-cotton-jumper-blue.0600337005.html
While the outfits can't really be mixed/matched, they are all things I will be comfortable in, day into night (we probably won't change for dinner) and footwear really is the most important part for this trip as we will be on our feet all day. I will probably bring a parka and a lighter Uniqlo roll-up jacket, as I want to keep packing to a minimum!