Try It With: Footwear with lots of structure, like thick-strapped sandal pumps, ankle booties, heavy canvas sneakers and pointy-toe flats. Avoid any style that stretches on your foot, like ballet flats or lace-up heels, though—it will cause the socks to bunch up.
Why It Works: A cozy anklet softens the severe shape of a architectural shoe (and keeps your toes warm as well, of course).
Click through to shop the look.
Natalie Joos (FilmMagic), Vistoria Sekrier (Getty Images), Susie Bubble (Getty Images)