For a sport that always finds itself at the vanguard of technology, the evolution of cycling style often seems to lag a few years behind the advancements of its bikes.

Often, something new will come along – longer sleeves or higher socks, for example – in the name of aerodynamic gains for the sport’s most elite riders. It’ll be considered outlandish, only to trickle down to the consumer level and define what cycling looks like for the rest of us several years later.

Rapha has posted losses for the last seven years, with a spokesperson telling Cycling Weekly — following the publication of its 2023 accounts — that the company is focusing on “profitability and resilience while the sector remains challenged”. Despite multimillion losses, the ‘Classic Jersey’, and all it represented, gave designers runway to challenge the very concept of what cycling style can and should look like.

The witty slogans slapped across the kit, such as “pretty ok at bikes”, speak volumes. But Ostroy – which manufacturers all its kit by hand in a factory in North Italy – also trades in high-minded design, such as a jersey made to look like a watercolor painting, while embodying its New York City pedigree with in-your-face kits featuring all-over floral print and jerseys splattered with the names of iconic punk rock bands.

However, British brand Fat Lad at the Back argues that a typical cyclist is anyone who wants to cycle (which, as a 6’4”, 255-pound rider myself, is an approach I deeply appreciate). And while some brands like to tout the fact that they do have some selections for us larger riders, Fat Lad at the Back puts those riders’ needs at the fore (though, it should be noted while the brand offers sizes up to 8XL, they also have small, medium, and large selections).

While the brand has plenty of design options and approaches to choose from, perhaps its most well-known, long sold-out offering is a trio of jerseys, all of which feature reimaginings of famous brand logos as things we’ve all thought while in the pain cave. “Make It Stop” reads a Michelin-style logo. “Very Tired” in place of what could read “Land Rover.” And, in lieu of the old Marlboro cigarettes sigil, the words “I’m Over It.”