What To Pack For A Holiday

Summer offers a feast for the senses. Unfortunately in a big city that can often mean the burn of heat rising off pavements underfoot, sweltering sleepless nights, even more tourists than usual, and jealously watching people enjoy the sun from your office window. What better time to book a holiday?

Right now the only destination on my list is the Hamptons. Close enough to the crackle and pop of New York City to make you feel connected, but beachy enough to resemble an actual holiday destination – and if it’s good enough for the Kennedy clan, it’s good enough for me.

The only issue with a hybrid destination such as the Hamptons – or indeed the likes of Barcelona or Sydney – is what to pack. This isn’t a beach in Goa where all you need (at a push) is a pair of flip-flops and some swim shorts. Nor is it a proper city break where at least one smart suit is essential.

The best place to start? Your luggage. Good quality luggage will not only encourage you to pack correspondingly elegant clobber, it will also gain you massive brownie points among the waspy set. A 30” Globe-Trotter case in a shade of midnight blue or hot pink should fit the bill.

Pack correspondingly – plus 20 per cent. So, if you think you need five shirts, take six.

You then need to imagine how your days will pan out in the Hamptons and plan your outfits accordingly. If, for instance, you see yourself sitting on the beach every day, having dinner locally every night and venturing into the city no more than once, pack correspondingly – plus 20 per cent. So, if you think you need five shirts (you won’t) take six – a mix of Turnbull & Asser’s long- and short-sleeved shirts will do nicely. You never know what situation you may find yourself in on holiday – some fading former deb with pots of cash and a penchant for powder-blue shirts may be looking for a dapper gent to bequeath her assets to – we’ve all seen Grey Gardens.

Now to the contents of your case. Assuming the aforementioned itinerary is correct, you’re going to need at least two pairs of swim shorts – opt for dark colours, cut around four inches above the knee. Shorts with side adjusters are far superior to those with pull cords.

In terms of footwear, the key is to invest in pieces that can be carried over into evening. A beautiful pair of sturdy leather sandals and some understated espadrilles in suede should suffice. Throw in some tan loafers and you’re good to go.

Next, buy at least two knitted polo shirts, which can be worn as easily on a sun lounger as they can beneath a jacket. Turnbull & Asser has a wonderful selection for summer, available in stores only. Another tip is to wear some slim jeans, a pair of white trainers, a plain T-shirt and a crew-neck jumper on the flight over – this will be the only casual garb you’ll need for the rest of your holiday.

Evening-wise, pack one pair of navy chinos and a pair in stone, both of which you can roll up to reveal your new brankles (brown ankles – one of the major benefits of a beach holiday). Additionally, invest in a light linen jumper (breathable in the heat) and three slim-cut linen shirts in pale shades of pastel, which you can wear in the evening or thrown over your shoulders at the pool. A grandad-collar tunic is a great smart-casual option if the fuss of a classic collar gets to you in the heat.

Pack two jackets, one dark and one light, which you can interchange throughout the week – fabric-wise, linen and super-light seersucker are best. Linen jackets from Turnbull & Asser are perfect for this – pop in to one of its stores to find them. When it comes to colour, shades of sky blue and navy are the most flattering against tanned skin. Just be sure to get an iron sent to your room – linen doesn’t travel well, after all.

Given the simplicity of your summer outfits, a few well-placed affectations, such as Turnbull & Asser cufflinks, will give you the edge while lunching at La Plage.

Finally, the accessories. Given the simplicity of your summer outfits, a few well-placed affectations, such as Turnbull & Asser cufflinks, will give you the edge while lunching at La Plage.

First, your sunnies. It’s all about round tortoiseshell shades right now, so invest in a high-quality pair with some metal detailing. Next, a light summer scarf with a subtle pattern. Rolled up under the crew neck of your linen sweater or worn under the lapel of your jacket, it will add depth to an otherwise one-dimensional outfit. A leather tote is a beach essential – that ‘bag for life’ you were thinking of using will not go down well in Long Island. Finally, a good-quality Panama hat will add an air of sartorial sophistication to any summer outfit – see Julian Sands in 1985’s A Room With a View for inspiration.

And there we have it – your holiday packing all packed up. Which leaves me with little left to say other than it is absolutely imperative you invest in some new underwear for your holiday, in addition to some of those slightly awful (but absolutely essential) invisible socks. Turnbull & Asser’s boxers are as light as they are long-wearing and perfect for summer trips, while its breathable cotton socks will work well under trousers. Clammy feet and old boxers do not an attractive prospect make – for fading former debutants, or anyone else for that matter.