Rihanna Grounds London Street Style With Timberland Boots and a Varsity Jacket

On November 28, 2012, in London, Rihanna was photographed stepping out of her hotel in a street-style look that balanced comfort, edge, and unmistakable footwear confidence.

Rather than leaning into performance glamour, she opted for an off-duty uniform grounded by rugged lace-up boots, proving how practical shoes can anchor a layered, menswear-inspired outfit without sacrificing attitude. The moment captures a recurring theme in Rihanna’s street style: using strong footwear choices to give structure and intent to otherwise relaxed silhouettes.

Rihanna was spotted exiting her London hotel on November 28, 2012, wearing her red-and-black Joyrich Freshman varsity jacket, skinny jeans, and Ray-Ban Wayfarer sunglasses with Timberland Premium Boots in wheat nubuck, finished with a leopard-print suede backpack by Pierre Hardy (Credit: Spiller / WENN)

The look leaned fully into Rihanna’s signature brand of street-chic layering, pairing a red checked varsity-style bomber with slim denim and sturdy lace-up boots that grounded the outfit in both function and attitude.

At the center of the ensemble was Joyrich’s Freshman varsity jacket, identifiable by its bold Rich swoosh logo. This piece reinforced the outfit’s collegiate edge without overpowering its casual ease. The styling worked precisely because the footwear remained practical and unfussy, allowing the jacket to read as a statement rather than a costume.

She completed the look with dark skinny jeans by James Jeans, Timberland boots, Ray-Ban Wayfarer sunglasses, and Pierre Hardy‘s leopard-print suede backpack—an example of how rugged shoes and luxury accessories can coexist seamlessly in off-duty street style.

Captured in a moment of casual elegance, Rihanna dons Joyrich’s ‘Freshman’ varsity jacket, adorned with the distinctive Rich swoosh logo, showcasing her unique blend of street style and luxury

Rihanna’s Enduring Influence on Timberland Street Style

From off-duty airport looks to city street moments, Rihanna has consistently shown how rugged footwear can become a deliberate style statement rather than a practical afterthought.

Her repeated use of Timberland boots—styled with everything from denim jumpsuits to layered streetwear—helped cement the brand’s place in high-fashion conversations while keeping its utilitarian roots intact.

The following related features explore how Rihanna and Timberland continue to intersect across street style, celebrity fashion, and footwear culture.