What is Alessandro Michele’s take on this iconic Jackie bag, and why the latest iteration was launched during the menswear fall/winter 2020 show

The Jackie is one of the brand’s most celebrated icons and possibly the most famous hobo bag in the world, the Jackie has undergone several transformations over the past six decades and continues to remain well-loved by the fashion set.

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Its latest incarnation of the Jackie by Alessandro Michele sees it streamlined, pared-down and shrunken. It’s now more versatile than ever: with multiple ways to wear it, more sizes, and—true to Michele’s style—is non-binary too. In fact, the bag was launched during the menswear fall/winter 2020 show.

We got five Tatler friends, Calista Cuaca, Dawn Koh, Dyon Foo, Tan Min-Li and Suhina Singh, to tell us what they love most about the Jackie 1961 bag.

Calista wears a peonia lace crew-neck, short sleeve mini dress with contrast white collar and tulle tiered skirt with velvet bow details, wool knit headcover with embroidered ears and burgundy velvet bows and white pompoms and the Jackie 1961 mini hobo bag in light pink leather.

The classic shape is now contemporary too

"What I love about the Jackie bag is the timeless half-moon silhouette. The latest one, interpreted by Alessandro Michele, maintains its original shape and elegance but is also so fun too, with its clean lines. If I could choose, I’d pick the Jackie 1961 mini in GG Supreme Canvas. I would pair it either with a neutral-hued cardigan and denim shorts for a casual look, or a bold checkered blazer with cowboy boots for an all-out ensemble!"

Calista Cuaca 

Dawn wears an oxford shirt, fine mohair intarsia crew-neck with embroidery details, Silver metallic nappa pants, hair accessory in metal with palladium finish and crystals and the Jackie 1961 mini hobo bag in black leather.

It comes in three sizes now

"Out of the three sizes available—medium, small or mini—I love the dainty-sized mini as a fun crossbody bag, and the small because it’s such an everyday bag on the go, in a classic hobo where I can dump everything I need (and more!) in. I have a soft spot for big bags for its practicality, and the Jackie 1961 checks that box. I love the small Jackie 1961 in GG Supreme Canvas: it’s one of those retro, evergreen bags that would go with my wardrobe which is filled with a lot of denim and blazers. I could wear this bag 10 years down the road and I won't tire of the pattern."

Dawn Koh

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Dyon wears a popeline micro sand long sleeve shirt with contrast embroidered collar, detachable jabot and velvet bow, velvet jacket and the Jackie 1961 small hobo bag in GG supreme.

Anyone can wear it

"The newest incarnation of Jackie 1961 bag that Alessandro Michele has updated references its codes and yet is a vision of modern design. It isn’t just suitable for all ages, it’s also versatile enough for any gender to wear, through the perfect melange between masculinity and flamboyance. If I were to style my Gucci Jackie 1961, I'd choose the white leather in the mini size because it is everlasting, elegant and extravagant! I’d pair it with a cream-coloured silk poplin shirt, black floor-skimming high-waisted trousers, oversized camel wool blazer jacket, and a pair of black patent leather boots."

Dyon Foo

Min-Li wears a vintage check sleeveless cropped shirt, viscose crêpe cady long pencil skirt with all-around ruffle details, tulle gloves with satin bows and crystals and the Jackie 1961 mini hobo bag in light purple leather. 

The shoulder strap makes it so versatile

"The distinctive piston clasp just catches my eye all the time; and the new shrunken size has made me fall in love with the Jackie all over again. The new (optional) shoulder strap gives it a casual vibe and makes it so versatile and hands-free, it’s perfect for a lunch date with the girls, and then shopping. Then just remove the shoulder strap for a more elegant look for the evening!"

Tan Min-Li 

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Suhina wears a shiny leather belted corset, soft brushed herringbone coat and Jackie 1961 small hobo bag in light blue leather. 

The pastel hues are delightful

"The pastel coloured Jackie 1961 bags are just adorable, and if I had to pick only one, the light blue hue is my absolute favourite. Though it was a tough fight, the other colour options which are butter, light pink and lilac are so delicious too! The candy colours now really pop against Alessandro Michele’s interpretation of this almost 60-year-old design. It’s a facelift, and Jackie now looks more youthful than ever!"

—Suhina Singh 

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