There are several theories on where and when the term “tomboy” originated. Dating back to the 1500’s, the Oxford Dictionary of English, proclaims “tomboy” as a “rude, boisterous or forward boy.” However, just a few decades later (according to Wikipedia) the term morphed into slang for a “bold or immodest woman.”
Today, the definition and the word itself evoke a wide range of reactions. For some, it feels archaic and rooted in outdated gender expectations; for others, it remains a term of endearment, synonymous with independence, confidence and a spirited disregard for convention.
Without debating the trappings of the term, of which there are many, I think we can agree that it is no longer a potentially negative thing? That women today might feel relieved knowing that they may behave and dress however they like. To me, a woman who feels liberated to explore every facet of her identity embodies the most powerful expression of the divine feminine.
Fashion has long celebrated women who embrace the tomboy ethos – Katherine Hepburn, Julia Roberts, Chloe Sevigny, Jane Birkin and Diane Keaton to name a few. These women exude femininity despite their lack of conventionally sexy or girlish attire.
In 2026, the look retains the same irreverent spirit, with a subtle evolution. It’s a cropped Oxford, buttoned up to the collar. It’s a long linen board short paired with Puma sneakers. It’s a silky dress worn with Converse sneakers. It’s wearing whatever feels right, even when it skirts societal expectations. A quiet act of rebellion and confidence executed with grace.
At the Top: The Tomboy, By John George Brown 1873
Coco Hinoki Perfume, Boy Smells
Wayfarer Sunglasses, Jean Therapy
Globo Shirt, Em’s
Oncept Boca Multi, Orleans Shoe Co
Oversized Tee, Lekha
Cotton Short, Weinstein’s
Foundation Henley, Angelique Boutique
Paracord Bracelet, Baublebar
Kiwi Button Up, Pronto
Vibe Check Sunglasses, Moxlox
Teva, Orleans Shoe Co.
Tommy Bermuda Denim, Angelique
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