Tomboyish blogger Maya Villiger’s site Turned Out has won her an admirable following—not just with readers but with fellow web gurus (Phil Oh and Hanneli are both fans), and even international style bibles such as Harper's Bazaar. A New Zealand native, now based in New York, she started the blog in 2008, posting daily updates of street style snaps of her friends, personal wardrobe and trend mood boards. Villiger’s style channels the androgynous/preppy look of Diane Keaton in Annie Hall—her staples this season include jeans from Rag & Bone, an APC boy’s sweater, and a Céline khaki coat. Who better, then, to celebrate the 30th anniversary this year of Robert Clergerie, the man who pioneered girl-meets-boy footwear in the 70s with women’s Oxfords created on men’s lasts? In homage to the French designer, we asked Villiger (a lifelong fan of the brogue and loafer) to choose some of her favorite ways that chic girls rock male-inspired shoes. Take a look at Clergerie’s iconic creations—and some beautiful vintage editorials in which they feature––here. 

Spread One

Left: A little tomboy, a little monochrome, a little Annie Hall—very cute.

Right: When I saw Katy in this I thought, “That's how you do it!” Brogues can feel masculine, but with a sweet floral skirt they look refined and chic. 

Spread Two

Left: When it gets cold out I think it's nice to break dark ensembles up with light pieces. Now I want to replace my pale Vans with a pair of old scuffed white loafers. 

Right: My first pair of fancy shoes were penny loafers—I treasured them. Now they remind me of playful moments in my early teens, and I love this picture of Molly mucking around in hers for that reason.

Spread Three

Left: Caroline and her vintage loafers, straight from the 70s––I’m definitely a fan.

Right: Marina’s look is not at all obvious, and so cool: harem pants, a denim shirt tucked in tight, and brogues—I like it.