I never thought I’d have anything in common with Vivian in Pretty Woman, and yet I have. It’s not the dream of being rescued by a knight in a white limousine, nor the length of our legs (since the whole of me is roughly two thirds as long as Viv’s hip-to-toe measurement).

No, what we have in common is that we both know what it’s like to feel underdressed. Her, when she tottered into one of Rodeo Drive’s most prestigious outlets in six-inch heels and a Spandex situation. Me, because I have a figure built for function not fashion. This makes glamming up challenging. 

As a result, I gave up shopping decades before it became fashionable to do so.

My wardrobe is described by friends – affectionately, but with regret – as “sackcloth and ashes”. I feel that by wearing a smile, I can make my clothes – old, second-hand or both – make do, and in the comfort of my local environment, that works just fine.

The trouble arises, of course, when I find myself in unfamiliar climes: black-tie events; cocktail parties; ­weddings – all of which I habitually swerve – and then that most unfam­iliar environment of them all: the ­holiday. 

If we’re talking beach hair and kaftans, no problem. But as soon as we venture into dressing up for ­dinner, or the sort of place where holiday equates to fashion parade, I’m in trouble. I’ve yet to take a cruise, because the formal evenings would leave me, frankly, all at sea.

So when I was given the opportunity to travel to one of the most glamorous places on Earth – St Barts – I hesitated. The tiny, once Swedish but now French Caribbean island of Saint-Barthélemy is best known for its headline-grabbing superstar visitors (among them Leonardo DiCaprio, Beyoncé and Elton John), the superyacht-owning oligarchs who go there to party, and its designer stores, which leave their Bond Street, Champs Elysées and Park Avenue counterparts standing, not only for their range of merchandise, but also because they’re tax-free.

But then I wondered, might there be a place for my charity-shop chic on this most stylish of isles? After all, isn’t the truest sign of wealth being able to dress exactly as you wish? Perhaps people would assume I was simply an off-duty dowager in my T-shirt and 10-year-old slacks.

And so, keen to find out, I went.

I arrived on St Barts several weeks later, on an eight-seat Tradewind ­Aviation turboprop plane from ­Antigua, and went straight to my hotel – Le Sereno, an iconic edifice that’s regarded as the ultimate embodiment of St Barts luxe. 

I unpacked in my room, unable to shake the feeling that the wardrobe – confronted with my ­garments – was ­giving me the same ­disdainful expression as the shop ­assistant gave Vivian on Rodeo Drive.

Then, still in my T-shirt and slacks, I gingerly made my way downstairs. I had arranged to speak with Samy Gachem, the hotel’s managing director, keen to hear what an island resident thought of my little experiment.

“The thing is, we are a luxury resort, but people’s definition of luxury is hugely variable,” he told me. I felt a little better. 

“Of course, some things are ­constants – our guests want the best service, facilities, food, design, location, and that’s what we provide. But beyond these fundamentals, people’s expect­ations differ. Let me ask you, what does luxury mean to you?”

To me, I told him, it means comfort. In my book, this translates as elastic-waisted bottoms, baggy T-shirts, wash-and-go hair, and trainers.

“Cool,” he replied. “You’re no different to some of our celebrity guests. We’ve had Bafta-winning actors dressed similarly. You are not alone in rating being able to look and dress how you please as a luxury. Le Sereno is five-star, but we’re all about relaxation. 

“Everyone receives the same welcome whether their style is smart smart, smart casual, casual smart, or casual casual. We don’t want anyone to feel intimidated by a dress code.”

Buoyed by this assurance, I headed off to dinner, dressed in a frock from a shop that time forgot, and shoes that were slightly too big.

Downstairs, there was a mixed crowd – some glittered in designer clothes, others wore smart leisurewear – all were better dressed than me. Even the staff. It didn’t seem to matter. No one stared, no one gasped, no one looked down their nose. I felt totally at ease.

The next morning, I chatted to a regular visitor over breakfast, who gently tried to shift my perspective.

She said: “Of course, the island attracts wealth – particularly during Christmas and New Year, when the superyachts plough into Gustavia, the champagne corks pop, and the ocean turns to Krug. But if you come here just to see and be seen, then you’re coming for the wrong reasons. 

“St Barts’ greatest attractions are free – the sea, the mountains, the natural pools. You don’t even have to get into the water to see turtles. Just look out now and you’ll see their little heads bob up. The lagoon is full of them.”

I agreed with her wholeheartedly, but still felt I’d be missing an important aspect of St Barts if I skipped its ritzy side. Sure, I could hide out by a natural pool in my kaftan, but that wouldn’t really answer my question.

Instead, I headed for Gyp Sea, a restaurant in über-fashionable Saint-Jean, where the crowd was Mykonos and Ibiza rolled in gold and dressed in boho chic – a style only the long of limb can carry off. I sat – short, squat and awkward – until I realised that again, no one was staring. The staff were warm and welcoming, and gradually my anxieties began to melt.

Next I headed to Sella, a restaurant near Gustavia, and walked immediately into a human wall of Gucci, Pucci, Fioruccio. This was the St Barts of celebrity magazines. The people were beautiful, either by nature or surgery – but most beautiful of all was their total lack of snobbery.

I’ve been to far less grand places where I’ve been made to feel so out of place that I barely tasted the food, but here there was no such meanness. I ­people-watched as I ate.

There seemed no hint of rivalry or competition between the guests, as you might expect of such a dazzling group. Had I found paradise? Could the world’s most glamorous place also be its least judgmental?

The next day, I visited the sublime Piscines Naturelles Grand Fond, which fill and empty depending on the tempestuous vagaries of the Atlantic Ocean. I had forgotten my swimming costume, so elected to test my new theory by taking a dip in my undies. To my astonishment, people smiled and gave me the thumbs up.

I’d gone to St Barts expecting to meet pretentiousness and elitism; to find people so obsessed with appearance that they would treat with condescension someone who so obviously lacked both the means and the inclination to follow fashion. 

I’d gone there, truthfully, expecting to ridicule their lifestyle. Instead, I left with an awareness that the only snob on the island was me. St Barts taught me a valuable lesson. Live and let live – and, above all, do not judge.


Xenia Taliotis was a guest of Le Sereno St-Barthelemy (, which has doubles from £862 per night based on two sharing, including à la carte breakfast, round-trip airport transfer and service charges. Tradewinds ( operates shuttle flights to St Barts from Antigua, San Juan, Saint Thomas and Saint Croix

Have you been to St Barts? What are your holiday fashion essentials? Share your thoughts below


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