How to Master the Art of the Headscarf—One Editor Shares Her Hack

I’ve just come off a weeklong holiday in Capri, Italy, during which I wore a headscarf every day of the week. Monday was a blue and white floral, Tuesday brought out some gingham, and come Wednesday, I wore a scarf in a bold red, the same shade as the tomatoes in the many Caprese salads I lunched on. The rest of the week continued as so.

My particular inspiration came from a photo taken in 1970 by Settimio Garritano, featuring Jackie Kennedy Onassis walking in Capri with a view of the Faraglioni in the background. She’s wearing skimpy leather sandals, a pair of light blue trousers, her signature oversized shades, and a headscarf tied in a point at the back of her head. The image, which I referenced a week before my own trip, led me to embark on an online quest to find the perfect headscarf à la Jackie.

Unlike other odysseys relating to the Capri region, mine was a very short one. I happened upon a selection of scarves at Free People and knew I needn’t look any further. There, I found an assortment of hair accessories that were not your grandmother’s (or Jackie’s, for that matter) scarves. Time and technology have brought to us what I am dubbing the fool-proof headscarf. It’s not a silk square, to be folded into a triangle and tied at the nape. This can create a bulky knot and any movement of the head could very easily shift things around. No, these scarves were pre-cut into triangles (no excess fabric!) with an elastic band (no tying necessary!) Some even featured decoy strips of fabric to trick the eye into thinking somewhere at the back of your head, a knot was tied. Let’s call it the equivalent of a pre-tied bowtie.

The benefits of this kind of headscarf are numerous. They’re a breeze to put on and the slim elastic ensures they’ll stay in place and not create bulk beneath long hair worn down.

It all seemed like a no-brainer, and that’s how I ended up in Italy with enough headscarves to last me my entire trip. There, I also came to appreciate Jackie’s look as one of both practicality and fashion. Capri is an island that encourages daily swims and, if you have access to one, afternoons spent zipping around the blue waters by boat. Plus, the air is heavy with humidity and the seas are extra salty. All these scenarios do not agree with my extra thick and frizz-prone Middle Eastern hair. My headscarves were the perfect way to keep me from thinking about the state of my hair and just enjoy the day.

As far as traditional silk squares go, I’ll keep them around for tying around my neck or handbag but it’s pretty unlikely I’ll attempt to sport one in my hair. Instead, I’ll wear any number of the below worry-free, fool-proof headscarves.

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