Simon says: 'Head attire has been creeping back into fashion for sometime now. At the recent mens shows it went front row on editors and celebrities. Also, this straw fedora is a stylish way to protect your head from the sun' £35 (Buy)Photograph: liberty.co.ukSimon Says: 'Polos are useful, they can be dressed up or slung on for the beach. This year go bright. If you care about such things, orange is particularly fashion forward' Was: £94 Now: £47 (Buy)Photograph: farfetch.co.ukSimon says: 'Bad Traffic Wardens. That's what so many men think of when they think of short-sleeves. It's frankly very old-fashioned. Short-sleeves shirts are like posher t-shirts. Truly' Was: £38 Now: £30 (Buy)Photograph: debenhams.co.uk
Simon says: 'Here's an easy rule: flip flops for pool/beach, sandals for everything else. Admittedly, these ones are a bit posh but they're classic enough to get out next summer too' £231 (Buy)Photograph: lanvin.comSimon says: 'These are statement trunks, which is reflective of the price. They're also good quality, which means they'll double as day shorts and wash well, so you can wear them again next year' £80 (Buy)Photograph: ralphlauren.co.ukSimon says: 'Obviously sunglasses should first and foremost flatter your face. This is down to the individual and requires trying on. But, in terms of total classic, Ray Ban Wayfarers never date. Tortoiseshell is a nice break from black too' £120 (Buy)Photograph: raybans.comSimon says: 'Once you've got the hang of tailored shorts - start with navy or stone - you can progress to something with a bit more punch, like these pool blue numbers' Was:£65 Now:£23 (Buy)Photograph: reissonline.comSimon says: 'Advice: super skinny chinos in the warm defeat the purpose. This pair in classic khaki are tapered and slim instead, making them literally cooler. For fashion points, roll up' £75 (Buy)Photograph: selfridges.comSimon says: 'Travel bag. Sightseeing bag. Beach bag. Is there a more versatile holiday bag than a rucksack? No' £59 (Buy)Photograph: selfridges.comSimon says: 'I never leave for a holiday without a grey marl sweatshirt. Wherever I'm going. They're useful, comfortable and go with everything. Shorts with a sweatshirt is a brilliant evening holiday option' £28 (Buy)Photograph: topshop.co.uk
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