“If I could summarize my style in two words, it would be French schoolboy.” Alessandra Calabi

Cultured and poised beyond her years, I fell right into Alessandra’s depth when she opened the door in her red cashmere sweater, high waisted jean shorts, and ballet flats. She never likes to look “too smart,” so there is always the “dressed down” piece, like her jean or black leather jackets that throw off her otherwise undeniably simple good taste. Her style is rooted in some of the enduring tenants of being born Milanese, where labels are about “tailoring and fit” and not trends. However, her signature of piling up bracelets on one arm reflects her strong sense of individuality and fervor for self-expression – she admits to feeling lost without them. Clothes, their details, and the way they feel (not “fashion”) make Alessandra happy, like thick textured tights with short suede shorts and knowing how pretty the lining is inside a jacket. Similar to how self-assured she is in her style, like some classic variation of a black flat everyday (no matter what new wedge is on the shelves of Topshop) is her unwavering obsession with 19th century British literature, plays by Moliere or Chekhov, philosophy, acting, set design, and screenwriting. There is nothing frivolous about Alessandra – she is a self-professed book-worm, feels that the theater is her natural habitat, and is the most comfortable in her striped nautical shirt, skinny belt, and beret.

If you like Alessandra, you might also enjoy Lexie Smith, Rachel Smith, or Carly Mark.