The Best Socks To Wear With Mary Jane Shoes In 2025

When it comes to shoe trends everyone will be trying in 2025, expect to see a lot of Mary Janes incorporated into street style. Mary Jane shoes are a type of loafer that have a rounded closed toe and a strap across the middle. Available as flats, platforms, or heels, these shoes can be worn with pants, tights, and dresses to fit with varying aesthetics. Even Kate Middleton is proving to be a big fan of trendy Mary Janes due to their classic look and comfortability. They are chic enough to make their own stylish statement but can be taken to new fashion heights when worn with the right pair of socks for extra warmth.

Cynthia Kennedy, personal stylist, image consultant, and creator of Your Style Transformation Academy, tells Glam exclusively that choosing the best sock is all about balance. "Mary Janes already have a sweet, structured feel; pairing them with slightly sheer crew socks, ribbed ankle socks, or lace-trimmed styles adds just enough charm without overwhelming the shoe. The sweet spot is a sock that adds personality without competing with the shoe." She says this can relate to the socks' length and the type of material it's made of. "Think soft crew socks that hit just above the ankle — not too high, not too low. A little ribbing or sheerness goes a long way." This type of sock also brings out the main feature of Mary Janes — the strap — and really allows it to shine.  

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."