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Why I Need To Stop Dressing Like A Fictional Version Of My 'Best Self' On Holiday

The gap between how I think I look on holiday and how I then appear in photos is so wide it sometimes takes me aback...

‘I like your dress,’ the semi-sleazy barman in the hotel bar said to me on our fourth night in Greece last month. ‘Did you buy it from the hotel gift shop?’

Reader, I had not bought my dress from the hotel gift shop. I had bought it two years ago from & Other Stories, which is where approximately 70 per cent of my wardrobe comes from. But when I packed my white, sixties-style smock dress with black embroidery and fluted sleeves, it was with Greece in mind.

Because in my head it was the perfect dress to wear in the fictionalised, rustic, vaguely retro version of Greece I’d imagined myself in - part Mama Mia, part Leonard Cohen’s 1960s haunt. And this isn’t a first time I’ve transposed all my hopes and dreams for my holiday, and indeed life, onto that holiday dress. I had high hopes for said dress on a wine-tasting tour of Rioja (just the thing to wear as I cycle through picturesque vineyards in the sunshine!), island-hopping in Croatia (just the ticket as I casually lounge on the back of the boat!) and for a fortnight in Cape Town (I’ll definitely want to wear that dress when I’m sipping cold chenin blanc and gazing out onto the harbour).

All of this is made only more ridiculous by the fact that Holiday Dress is perfect for none of these things. It packs terribly for a start – it’s a nightmare to iron and creases easily. It’s not particularly flattering unless I’m at my thinnest (which I resolutely was not when I went on holiday this year) and it’s one of several summer dresses I own that inspires people to give up their seat for me on the tube (spoiler: I’m not pregnant). It’s not a versatile dress, it’s a weird, scratchy, heavy material that makes it both too hot for a Mediterranean climate and a nightmare against sunburn (which I will almost certainly have from days two through to five of the holiday). And it’s a little too short to do anything other than sit down for dinner, stand up, and walk out of the room again, while self-consciously tugging at the hem.

Things you cannot do in Holiday Dress include, but are not limited to: riding a bike, getting on or off a tall bar stool, bending down to pick something up off the floor, drinking red wine if you’re at all spilly (ditto gazpacho), climbing in or out of cars, or on or off boats.

It is also too on the nose, too referential of my ideal personal style – it makes me look like I’m either in fancy dress, or taking the mickey. I have curly hair in a short bob with a fringe that goes almost spherical when left to its own devices, and a penchant for wearing hoop earrings and Birkenstocks. This is fine most of the time, but when I put on Holiday Dress, the overall effect is of a woman who has gone to a Dress As A Decade fancy dress party as the 70s.

This is not my intention. The only thing I’m supposed to be dressed up as in Holiday Dress, like all of Holiday Wardrobe is my ideal version of myself. Tanned and carefree, effortlessly stylish and surprisingly lithe for someone who goes to the gym so rarely. And never more so than on day four of the holiday when my tan is just developing and I put on my Holiday Dress.

The reality, as photos – and the hotel barman – remind me, is something different. I look like a sunburnt British woman who buys 80 per cent of her clothes for 20 per cent of the year and can’t wait to wear them all. But I still pack the holiday dress, year in, year out, because the association is there, and I can’t kick it. I’m like pavlov’s dog, only with a £45 scratchy dress and some Piz Buin factor 30.

And I know why I’m doing it – and probably why you do it too. I almost don’t want to type out the words… but I do it for Instagram. For the possible balmy sunset photos of me looking relaxed and happy having a #sundowner in my holiday dress. For the photos of me cycling through beautiful Vineyards, or sipping that cold chenin blanc and feeling #blessed.

Those posts don’t actually exist on Instagram – I never put them up - because the gap between how I think I’m going to look on holiday (or how I should look) and the resulting pictures is almost always too huge. It almost takes me aback sometimes, how big the difference between my expectation and the end result is. But every holiday I live in hope, dutifully pack my holiday dress and cross my fingers that this is the year the world gets to see the best version of myself, in my laid-back boho dress and four-days in tan, living my #bestlife.