Every fashion label has that one defining piece – the design that quietly becomes its signature. For Fairfax & Favor, that distinction belongs to the Regina boot. With its sleek knee-high silhouette, premium leather and distinctive tassel detail, the style has become one of the most recognisable pieces in modern countryside fashion.

And as the Cheltenham Festival kicks off this week, the Regina is once again expected to dominate the unofficial catwalk trackside. Among racegoers navigating muddy paths, grassy enclosures and long days on their feet, the boot has quietly become the go-to footwear for the event – striking that rare balance between elegance, comfort and practicality.

Its popularity has also spread well beyond the racecourse. The design has been worn by Zara Tindall, who was named a Fairfax & Favor brand ambassador in March 2025, as well as former Made in Chelsea star, Georgia Toffolo and sports broadcaster Clare Balding. Zara even wore the pair of the first day of the festival yesterday.

Yet the Regina’s success is no accident. According to co-founder Marcus Fairfax Fountaine, the boot was designed to embody the brand’s core philosophy: timeless style over fleeting trends.

“First of all it’s incredibly classic and timeless,” he explains. “It really is at the heart of our design pillars, which is timeless style.”

That commitment to longevity is deliberate. While many fashion pieces are created with seasonal trends in mind, Marcus believes the Regina has all the ingredients of a true wardrobe staple.

After selling more than 150,000 pairs worldwide, the Regina boot has already cemented its place as one of the brand’s most successful designs – and it shows no signs of slowing down.

Behind the elegant design lies years of careful development. The boot has evolved steadily since its early versions, with the brand refining its construction to ensure it works just as well in real life as it does aesthetically.

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The Regina boot is a tall, knee-high style finished with Fairfax & Favor’s signature tassel detail and an easy side zip, making it simple to slip on and off. It is designed to suit different fits too, with three heel heights and three calf sizes to choose from – narrow, regular and sporting – so you can find the shape that works best for you.

The boot comes in a mix of leather and suede colourways, including classic black and rich mahogany leather, alongside suede shades such as tan, navy and chocolate. If you are tempted to try the iconic style for yourself, you can shop the different Regina options below.

“The real secret is that boot has been changed, upgraded,” Marcus reveals. “We’ve added lining, introduced a new tassel, adapted the elastic panel, and upgraded the comfort with memory foam insoles and rubber soles.”

Those upgrades have transformed the Regina into something far more than a stylish statement. It is now designed to withstand long days outdoors – whether that is navigating the racecourse at Cheltenham or standing for hours at countryside shows.

“One thing about Regina which sets it apart from the rest is that we use full grain leather,” Marcus explains. “We use blade stitch construction, which is very but also quite flexible.”

The result is a boot that balances durability with comfort. The Regina is available in different heel heights and multiple calf fittings, making it easier to find a pair that feels truly tailored to the wearer.

From personal experience, that comfort is not just a design promise. After wearing my own pair for more than eight hours straight while working, I can confirm the memory foam insoles make them feel almost like walking on clouds – remarkably supportive even after a full day on your feet.

It is precisely that combination of craftsmanship, versatility and enduring style that has helped the Regina achieve cult status.

While fashion trends may come and go, a beautifully made boot that looks as good at the races as it does on a country walk is far harder to replace.

If Marcus is right, the Regina will still be stepping confidently through muddy racecourses and countryside paths a decade from now, proof that true style rarely goes out of fashion.