Vagabond Shoemakers Ansie Mary Jane Pump ($105, originally $175)
For Mary Janes with a slight edge, this pair fits the bill with its double straps, glossy finish, and chunky heel. We especially love them with sheer ankle socks, but you can also wear them without socks on warmer days. Our editor owns them and can’t get over how comfortable they are. For more details and to see how she styles them, read our Vagabond Shoemakers Ansie Mary Jane Pump review.
Editor quote: “Because the shoes are so comfortable, I feel confident wearing them to work events, coworking spaces, dinner dates, and even just long days outside of my house. They ooze a polished and preppy vibe that feels formal yet still playful; you can get away with wearing them to the office and straight to a cocktail party afterward.” — Kyley Warren, assistant editor, Shopping