After Burberry Prorsum sent their models down the runway in pumps and ankle socks in 2008, the trend has been evolving. Would you wear ankle socks with heels? Personally, I think it's super cute and I try to find really playful and patterned socks to wear underneath, although the trend seems to focus more on delicate, white and lace socks or plain black.
Other designers such as Marni, Prada, Christian Dior, Alexander Wang, Marc Jacobs, Hussein Chalayan, Rag & Bone, Miu Miu and Margaret Howell have used the trend recently on the runway. I think the ankle sock trend goes best with a pair of wedges and a short, billowy dress. However you can pair them with anything!