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Style Mavericks: Pushing Boundaries in the Fashion World

Writer's picture: Tom GoedhartTom Goedhart

Updated: Dec 20, 2024

If you’re a fan of top-tier street style photos from global fashion weeks, chances are you’ve spotted the tall, broad-shouldered man with a rugged beard and a style that blends elegance with a rebellious edge. Sound familiar?


That’s Justin O’Shea - the man fashion photographers chase at every major event.

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A Street Style Icon

Known for his razor-sharp wardrobe and Instagram following (over 100,000 and counting), Justin O’Shea is an unexpected figure in fashion. Hailing from Australia, O’Shea is a self-taught businessman who carved his way into the industry through determination and savvy.


In 2009, he became the Buying Director for MyTheresa, a German women's fashion retailer. Tasked with selecting and sourcing products, O’Shea helped transform MyTheresa from a small Munich boutique into a fashion powerhouse generating $130 million in annual revenue.

O’Shea’s accomplishments and signature style caught the eye of Brioni, the iconic Italian menswear brand known for crafting classic yet contemporary suits since 1945. The connection seemed natural, and in early 2016, Brioni appointed him Creative Director.


However, this role proved short-lived - lasting just six months - suggesting that even someone with O’Shea’s instinctual flair might find the fashion world a tough arena to navigate.


Undeterred, Justin O’Shea took another bold leap. In June 2017, he launched his own label, SSS World Corp, embracing a streetwear aesthetic with his signature touch.


O’Shea’s commanding presence, cold demeanor, and sharp style have earned him the moniker “Wall Street Fashion Gangster.” Let’s explore his unmistakable style elements:

Signature Accessories: Dark sunglasses, a full beard, and a knack for mixing unexpected patterns.

Fashion Power Couple: O’Shea’s partner, Veronika Heilbrunner, is a fashion editor with equally striking style, making them one of the most iconic duos in fashion.

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Sometimes he channels rock star energy with rebellious overtones.

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Other times, he keeps it simple - pairing a suit with a plain white tee.

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He masterfully layers shirts, ties, and overcoats with a bold mix of patterns and textures.


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Fearless Use of Color: From muted tones to challenging hues, O’Shea’s gritty, rugged aesthetic always stands out.

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Trench Coats: Knee-length trench coats are perhaps his most identifiable wardrobe staple.

Justin O’Shea proves that even an outsider can leave an indelible mark on the fashion world with confidence, creativity, and risk-taking.


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