Gorgeous girl Chiara Totire — she of legs-for-days and style-for-the-centuries fame, Anna dello Russo’s lieutenant and all-around master of Milanese style — is the latest stylist extraordinaire to vamp for our Vintage Wars!

Before she was one of fashion’s fastest rising stars, Bari-born Totire was working the 9-5 slog as a pharmacist in her hometown of Bari, in Italy’s sleepy Puglia region. When she realized her heart lay in hemlines and halter-tops, she packed up her prescriptions and moved to Milan. With some fire under her feet and a flair for fashion, she was immediately scooped up by go-to glossy, Gioia. After honing her styling skills there, her talent was spotted by the Captain-in-Chief of Couture, Anna dello Russo, and has been working with her at Vogue Japan ever since.

Though you may expect her style to be a page out of ADR’s little black (probably Dolce & Gabbana) book, Totire’s vibe is androgynous, minimal, but just flamboyant enough to be get chased down by stampeding street-style photographers every fashion week. She’s soft-spoken, thoughtful and creative in a way that comes naturally to the dark-haired beauty. “When I’m putting a look together, I can’t explain it,” she describes of her process, “sometimes the clothes just speak to me.”

Luckily for us, we got a little insight into her style-psyche as she dipped into the LDJ archive for a spot of one-on-one styling smackdown.

Let the Vintage Wars begin!

– Laura Todd

La DoubleJ Liberty Boy Shirt

Totire went for the day-to-night overalls look when styling her La DoubleJ Boy Shirt “I chose the pinafore because it was a more elegant contrast to the dungarees,” she explains, “with a similar shape but more formal.” And where to wear them? “The dungarees are a more comfy and everyday look, while the pinafore would be more suitable for a cocktail party, especially with a cluster of Ugo Correani vintage pins!”

La DoubleJ Bosco Boy Shirt

“I have an addiction to rockabilly,” Totire says of the badass rock look she’s just whipped up. “These looks are very my style. I have a lot of fun matching these shapes together.” Totire mixed her first look with a red belt that came from her mother’s closet. She opted for the opposite feel for the second look, where she layered La DoubleJ’s wildly fringed 1990s vintage Barocco jacket. “I had a lot of fun with this outfit — It’s easy to get a good picture with these kinds of pieces!”

1960s Vintage Houndstooth Coat

“I love the shape of the coat,” she gushes of La DoubleJ 1960s vintage duster. “I prefer to keep it closed with my arms crossed to highlight the big shoulders — crossing the arm gives it a great 50’s style.” As for the second look, she went more lady: “This Temperley of London dress just looks like it was made for the coat!” Simple as that.

La DoubleJ Tulipani Viola Happy Wrist Dress

“I like to wear this kind of dress with pants,” says Totire of flares and bell-sleeves dress. “I feel more comfortable wearing pants and the cuts of these pieces work amazingly together.” For the second look, she matched it with “a high-necked shirt to give the outfit a bit of lightness. I like this dress because it’s very 70s and large — very comfortable to move in.”

La DoubleJ Liberty Rosa Curly Swing Dress

“This is one of my favorite pieces from La DoubleJ Editions,” says Totire of one of our favorite new styles, the Curly Swing Dress. “This kind of look is exactly how I’m dressed all summer. When it’s hot out I never try too hard, so I like to wear long clothing and dresses — I love the flowiness when I walk.” Adding the cape from the La DoubleJ archive is an easy way to get 365 days of use out of the pattern-popping piece!