Technically, there is no wrong time to visit Capri, with all its sparkling beauty and wonder, but certainly, there are less than ideal times to be in Capri. The winter months are cold and rainy, with the sun only poking its head out an average of four hours a day, and fewer restaurants are open to sip an Aperol spritz in the afternoon. Still, winter in Capri is better than summer in many other places. This little island has a certain magic to it–with its seemingly glowing blue waters, colorful houses, and a seen-and-be-seen air at even the most casual of cafés–there is a reason it has been a destination since ancient Roman times when Augustus himself made Capri his very own luxurious resort.
Temperatures–and crowds–are ideal from April to mid-June, and again from September through mid-October. The summer months see the most visitors and for good reason. What better place to cool off from the heat than in the pristine blue waters in Capri? Long considered a posh getaway for the wealthy and would-be alike, visitors spend their days strolling, swimming, and sipping a drink or two. In this environment, a certain style has always simply been, a distinct kind of upscale casual known as Capri chic.
Below is a style guide for all those who plan, like Augustus did over two thousand years ago, to make Capri their very own luxury retreat.
First Things First: The Accessories
Before reaching for linen pants or a flowing dress, grab a wide-brimmed hat or a colorful headscarf. In the summer months, there are parts of Capri that only see the shade from the shops lining the narrow streets. Long a staple of Capri style, the wide-brimmed hat or bold headscarf is a must for sun protection and general coolness. After all, a wide-brimmed hat is more stylish than a sunburn on your nose. And don't forget to don dark sunglasses to complete the look.
For as much sightseeing, swimming, and shopping as can be done on Capri, it is a time-honored tradition to slow down and enjoy an afternoon cocktail. Take in the scenery while you sip on the popular Aperol Spritz, an Italian wine-based cocktail made with prosecco, digestive bitters, and soda water. This is where the all-important day-to-evening wear comes into play, because afternoon cocktails have a way of turning into evening cocktails on the island of Capri, and it's always best to avoid the chore of having to go back to a hotel room and change entirely. Visitors dress with the evening in mind, so they can sip away into the night, uninterrupted.
The Capri Sandal
Most of the moving about travelers do in Capri consists of leisurely strolls, and so a certain shoe has come to be relied upon for this stylish walkabout. A high-quality leather flat often adorned with colorful gems, the Capri sandal is perfect for navigating cobblestone. History buffs should plan to stop in Canfora, a famous made-to-order sandal boutique that counted Jackie O. among its clientele who wore the handmade sandals.
Capri Pants, Of Course
No trip to Capri could be complete without donning the stylish pants named after the island itself. Created by European fashion designer Sonja de Lennart in 1948, the Capri pants' became a symbol of casual Italian style, with movie stars like Grace Kelly seen strolling the shops here in her capris. Not-quite-pants and not-quite-shorts, capris are a stylish in-between for those who are not ready to commit to either.
Effortless Is The Best Accessory
Everyone who makes Capri their destination should dress to impress--not just to fit in with the locals and movie star visitors, but, most importantly, to feel that Capri magic themselves. Wearing bright blues to echo the otherworldly beauty of the Mediterranean Sea is a must. Of course, the best accessory is an effortless ability to go with the flow here. Travelers are encouraged to nurture their curiosity and explore all the island has to offer--from swimming and cliff-diving to shopping and strolling the cobblestone streets, to letting their afternoon cocktails turn into an evening under the stars.
When planning a trip to Capri, it is best to plan your arrival in the warm summer months, yet still, try to time it away from the crowds. Packing the essentials is key to enjoying the magic of this little island so that you can immerse yourself, however briefly, into the stylish luxury of a resort fit for emperors, first ladies, and glamorous adventurers.