Outside of the Kentucky Derby, hats might not be the starting point when planning your attire. Often it’s the rest of your True Fashionista outfit that takes center stage, and what might sit atop your noggin comes after the fact. Hats, however, can very much state the crowning glory of the whole presentation. (Ok we’ll stop.) They’ll cap off the outfit to make your statement and everything. (We’re done we promise…) Hats are actually among the accessories that get an update every year. You can find them in a myriad of colors and styles to suit changing tastes and trends.

Hats, in fact, have been around since around 3300 B.C., which is the time from whence a mummified body frozen in a mountain was discovered wearing a bearskin cap, and now we know when all this craziness began. Ancient upper-class Egyptians wore a headdress, and in the Middle Ages hats denoted status. Coco Chanel was a big fan of hats, as was Halston, who made his name first as a milliner before unleashing his talent on the rest of the wardrobe. Chanel saw the intrigue in framing one’s face in a proper hat and producing a line of wide-brimmed sensations before venturing out to develop the cloche. Fitted close to the head and framing the face, the cloche was the choice for a woman to be different, bob her hair and raise her hems at a time when the world was just not ready. Chanel took chances and it paid off for hat enthusiasts everywhere. Her styles are as relevant today as any time.

Before we go any further we do need to mention that perennial True Fashionista headwear of tropical paradise enthusiasts, the floppy and/or wide brimmed hat. Lola Hat’s Pergola style straw hat is a hot number at the moment, says Marie Claire. Ya gotta have one of these around here, but honestly, there’s sun everywhere, so a big floppy hat makes sense even when you’re not lounging near some waves. Marie Claire is also big on the Cuyana hat’s minimal, classy feel. If your big hat needs to be weatherproof, go for Eric Javits’ slick bucket number. However, if you’re venturing north and need to keep some heat up top, fashion is ready to go! With these pieces, you could always keep the wide brim, but consider going Derby-style with an elegant tulle scarf tied into a magnificent bow. Something Special carries a line of these, as does Department 56. Fascinators never seem to go out of style either, with companies like PippaAndPearl and Vineyard Vines delivering the goods.

Slouchy beanie hats are a hot item this year. Even here in our tropical paradise there are the occasional chilly mornings that make a thick cloth head covering a wise choice, or at least one that won’t overheat your bod. Dotbestproducts recommends a unisex  slouchy hat, featuring ultra-thick double layered stitching which makes the hat not only warm but flexible too. And bonus! It’s got a big, fluffy pompom at the top. Oxblood and cobalt are hot colors this year, insists Pouted.com.

We know, we know, they’re not hats, but personalized sparkling, statement hair pins were all over fashion weeks for this season and hey they go on your head and serve a purpose, so they’ll get a mention. Choose to spread awareness, show empowerment, or even just wear your name; there’s no limit to how you can style these. Whether you identify as a boss, believer or rockstar, these jewels will keep you looking sleek and stylish. You can even wear a few and rock an entire sentence on your True Fashionista crown

Find a great, always updated selection of crown-toppers at True Fashionistas Resale, online or in our Naples, Florida store. Bring it on, winter!
Jennifer Johnson