— Style —


Hildie Plumpepper Illustration by Jill Anthony, ©2019, Background by Brandon Smith
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Ahh Capri…with its azure shores, captivating beauty and Italian charm, it’s no wonder that it has long been a playground for the rich and famous. Capri has a free-spirited vibe that exudes a leisurely glamour, much like myself. In the 60’s and early 70’s, it was the place to be for the international jet-set.

In the past few weeks a curious thing was happening on my instagram feed. 

One image kept popping up. It was a photo of Jackie O on holiday in Capri, wearing exactly what I want to wear this summer and wearing exactly what I already have in my closet. The look was so simple. It was ageless and timeless. It’s amazing that the photograph was taken nearly 50 years ago!

I wanted to recreate Jackie’s chic look starting with her head scarf. With a silk patterned scarf tied neatly behind her head, it’s just the element needed to elevate this simple look to a vintage glam vibe. Of course, no Jackie O look would be complete without her famous oversized sunglasses. Darlings, after a night of wining and dining, what better way to hide tired puffy eyes than with a pair of big sunnies? Jackie O was really onto something here.

We all have a favorite summer tee that flatters our shape. I love Jackie’s high crew neck tee with its slightly fitted shape. In a dark navy blue it contrasts nicely with her crisp white capris. Legend has it that the capri pant was inspired by Italian fishermen who would roll up the bottom of their pants so as not to get them wet. In 1948, fashion designer Sonja De Lennart, who adored vacationing in Capri, designed a feminine interpretation of the fisherman’s pant. Jackie O’s version is cropped right at her ankle which I love.

A classic look needs a classic handbag. My Gucci hobo bag was renamed “Jackie” after the stylish First Lady was spotted using it to shield herself from the paparazzi. The bag has been relaunched several times and is still available today in an array of fabulous colors and patterns.

Making Sandals in Capri, Italy!

Jackie O’s Capri ensembles always featured a flat sandal. One of her favorites was the classic Jack Roger sandal, a timeless staple of vacation style. After returning home to Palm Beach, Jackie brought a pair of sandals she purchased in Capri, to a cobbler to recreate it. This was the start of the iconic brand.

Darlings, you know I love a fun tote bag. How else could I carry my adorable tabby, Roddy, and a bottle of Chianti? My straw tote by Poolside, with it’s charming “Ciao” stitched on the front, is ideal for some afternoon shopping.

So my fashionable friends, if you’re tired from all the “fashion noise” out there, let your senses take you to Capri, where the look is effortless and chic. When you get there, tell them Jackie sent you!

Ciao Loves!

XOXO, Hildie


  • Rena May 24, 2019 at 9:43 am

    I’ve always wanted to travel there and I’m sure I will try to replicate the styles. You can’t go wrong with Jackie O. She is the epitome of style!

  • Suelyn Farel May 24, 2019 at 4:07 pm

    This is a beautiful timeless look that we can all wear!! Love it! Also don’t forget when it is colder to transition from day to evening —it’s perfect around the neck or for a wrap!!

  • Donna O'Klock May 24, 2019 at 4:14 pm

    Love this look, Hilde. Now I’m fantasizing about the Italian coastline… that’s amore! Also, I’m really enjoying your illustrative collaborations with Brandon, always beautiful.

  • Hilda Smith May 26, 2019 at 12:47 pm

    I just love everything about Jackie O’s style. Beautiful look Hildie x

  • LA CONTESSA May 26, 2019 at 7:56 pm

    I have been ONCE and we were still allowed to swim in the GROTTO back in the 1970’s………SO BEEN THERE DONE THAT!

  • Dawn May 29, 2019 at 6:51 am

    Is that supposed to be you in the illustration? It certainly isn’t Jackie O

  • Sandra Sallin - Apart From My Art June 23, 2019 at 4:59 pm

    I adore that look. It is perfect. But I think I’m a tad too large for that so fitting T-shirt. But I love it and the look.I may not wear the scarf in my hair but definitely the glasses and shoes. Great look. Thanks for bringing it back.

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