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Holiday packing is a tough thing to nail. Given it's the occasion we shop for least (compared to work and nights out in good old Blighty), we often end up reaching for the same 'safe' pieces we’ve had for years, or panic-buying something vaguely beachy the week before we fly.
The result? A wardrobe that feels slightly stuck in 2014. From kaftans to denim shorts, a lot of these staples are a fast way to 'date' your holiday look. The good news is, a few simple swaps can make everything feel instantly fresher and more modern, perfect for that poolside snap while you drink your Pina Colada.
It’s not that kaftans are inherently bad: they had a moment, and in theory they’re an easy option to chuck on by the pool. But sometime around 2018 they became a bit... much. It's now hard to find a kaftan that's not floaty, brightly patterned and covered in tassels a la Tanya from The White Lotus.
Then there's the fact that because they're so shapeless, they make you look bigger than you are. There's no cinching or accentuating your figure, which is what we all want when poolside. It's a hippy-dippy vibe that usually veers into looking dated, or like you’ve defaulted to the same holiday uniform everyone else is wearing.
A linen shorts and shirt set, on the other hand, feels more current. It’s still just as easy, but as with all co-ords the matching element looks considered. The structure of the shirt balances the relaxed shorts, and even if it’s oversized it doesn’t swamp you in the same way. You can wear it open over swimwear, buttoned up for lunch, or even dressed up with sandals in the evening for that chic, couldn't-care-less Scandi vibe.
Denim shorts are the undisputed staple of holiday dressing. They go with everything, and most of us have owned about ten versions (including those overly distressed holey ones) over the years. But, let's be honest – they're more suitable for teenagers at Glastonbury than grown women by the pool.
They’re also not exactly built for actual holidays. They cling, they ride up, and they don’t really give that easy, thrown-on energy you want when it’s hot. You spend the entire day uncomfortably shuffling around while your nether regions struggle to breathe in the stiff, thick material.
Boxer shorts, on the other hand, are a much cooler switch-up. They’re looser, lighter, and a favourite of laidback style stars like Kendall Jenner and Bella Hadid. The boyish shape gives that off-duty, borrowed-from-him vibe, and because they’re not skin-tight, they're way more flattering. Worn with an oversized shirt or simple tank, they look effortless in a way denim shorts just don’t anymore.
Gladiator sandals are the fastest way to make an outfit look like it's been plucked from 2014. All the straps, all the wrapping – they just make an outfit so much more fussy than it needs to be. That aside, they also cut your leg off at awkward points, which makes them look shorter and stubbier. No, no, no.
Minimal leather sandals, on the other hand, are clean, simple, and go with any outfit – without stealing all the attention. A basic pair in black or tan does the job without you having to think about it, and instantly makes you look more current. It’s a low-effort, quietly-put-together vibe that works so well on holiday.
Denim jackets always seem like a good idea when you’re packing, but rarely earn their place once you’re there. They’re a bit too heavy for the heat, too stiff and uncomfortable to throw on easily, and somehow always cut off at an awkward place around your middle. It’s very much a 'mum trying to look trendy' effect.
A lightweight knit or sweatshirt draped over your shoulders, on the other hand, works better. It’s there if you need it, but more importantly it adds interest to an outfit without feeling like a full extra layer. You can use any lightweight sweater you already own, and look more Instagram fashionista than Facebook mum.
Those strappy evening dresses – usually very thin and floaty – feel like the obvious holiday night option, but can be a bit of a let-down in real life. They often cling in the wrong places, hang awkwardly in others, and without much structure can end up looking more flimsy than flattering. It’s that in-between where it’s meant to feel dressed up but actually leaves you looking like a walking tent.
A structured slip or column dress is the more put together option. Slightly thicker straps, a bit more weight to the fabric, and a cleaner silhouette make all the difference. It still has that easy, throw-on appeal, but actually holds its shape and skims properly, so it works from dinner to drinks without feeling like a cop out.
There's a kind of group psychosis over big beach bags. The thinking is you can fit everything in them and never have to peel yourself off the sunbed because you've left something in your room. But let's be honest: that never happens. Firstly, you inevitably forget stuff anyway; secondly, the whole prepared-for-every-scenario vibe isn't particularly chic.
A softer, slouchy tote, on the other hand, is much cooler. It still fits everything you actually need, but doesn’t dominate the outfit or make it feel so planned. Thrown over your shoulder, it works just as well for the beach as it does for lunch or wandering around. It’s a small switch, but it makes everything feel a bit more relaxed.
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