Princess Diana and the Sloppy Joe Sweatshirt

When Princess Diana was alive, she was an instant style sensation. She could be seen in cycle shorts, oversized sweatshirts, sneakers and jeans as she stepped out for a gym session. This was a mix of high-end and low-end clothing that symbolised her status as a regular, relatable British citizen but still a member of the Royal family.

The princess was a fashion icon that never wore anything too ritzy but always looked like she was at the ready for an event of significance, whether it was an engagement or a royal wedding. She wore dungarees, oversized sweatshirts and cycling shorts as she walked from her house to the gym, a routine that was a big hit among the fashion press.

She would tuck in her cycle shorts to create a snug, but not too tight look, while her oversized sweatshirt was loose enough to allow her to move without feeling restricted. The result was a sexy, yet comfortable workout look that embodied the idea of “normal” and paved the way for other celebrity women to sport this outfit.

As the brand’s oversized, baggy styles made their way into the zeitgeist of the 1990s, they were rewarded with a special ‘Royal seal of approval’ when the late Princess Diana was photographed wearing her favourite Sloppy Joe sweatshirt in many public appearances. It was this that really cemented the brand into a must-have fashion staple and Tilletts has proudly stocked this popular style in their Cleethorpes store since it launched in 1993.

Sloppy Joe was launched in London by Jackie Harris over 30 years ago, it is ethically made in the UK from 100% organic cotton fleece and has been a must-have for stylish millennials ever since. The Sloppy Joe collection is available online and in Tilletts stores, with the ’05 Classic Square Sweatshirt’ – one of the original Sloppy Joe designs and the most iconic piece worn by Princess Diana – being back in stock and available to buy now.

The Sloppy Joe Collar 02 – a bestseller in the Sloppy Joe collection and championed by Princess Diana in the 1990s, this style features an open neck with stand up collar, rugby shirt appeal with ribbed cuffs and hem. Its smart-casual allure makes it a classic that has been relaunched after 20 years with the same quality fabric and bespoke Sloppy Joe colours all year round.

Alternatively, try the Straight Crew Sweatshirt. This style was one of the first Sloppy Joes to shoot to fame in 1993 and was worn by Princess Diana on numerous occasions; a true retro sweatshirt must have for fashion conscious millennials, it also comes in a range of bespoke Sloppy Joe colours that have been specially created to commemorate the Queen Mother’s 90th birthday.