The Best Socks to Pair with Mary Jane Shoes in 2025

Socks and shoes are meant to complement each other. Cynthia Kennedy points out that this is easy to achieve thanks to the unparalleled versatility of Mary Janes. “You can play them up or down depending on your vibe. With cropped trousers or midi skirts, they add instant polish,” she notes exclusively to Glam. For something that feels a bit edgier, consider wearing them with sheer socks or even a patterned sock to add extra texture. Or if you love nostalgia, “Princess Diana socks” that are trending for ’90s-inspired footwear might be what you’re looking for. She recommends, “Don’t be afraid to mix them with unexpected textures — a patent Mary Jane with a wool sock? So chic.” 

Kennedy explains how preppy styles including knee-high socks could be a bit harder to pull off correctly. “Keep in mind that depending on your age and how you style it, it can start to feel a little more costume-y than chic.” But so long as the style doesn’t feel inauthentic to you, it could be worth a try! To find the perfect sock, Kennedy relies on brands that she trusts, including Calzedonia and Tabio for sheer pairs. “For ribbed or neutral styles, Bombas and Le Bon Shoppe are closet staples,” the expert goes on. “They strike the right note between cute and polished, especially with a feminine shoe like a Mary Jane.”