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The top 5 most iconic Chanel handbags of all time

By Melanie Kruger  |  August 31, 2020
Image Credit: tinx/

When it comes to the most coveted luxury designer handbags in the fashion world, few houses have ever got it quite as right as Chanel. Despite the wealth of competition and a wide selection of women’s bags flooding designer boutiques from the likes of Gucci, Balenciaga and Louis Vuitton, there’s just something about this sophisticated brand that effortlessly trumps all others – making its bags the must-have accessories for the style conscious, year in and year out.

Unwrapping your very first Chanel bag is a truly special moment indeed, and if you own one, the chances are, it comes with a feeling you’ll never forget. Since the brand’s inception in Paris in 1910, it has gathered itself a legion of loyal fans, continuing to grow alongside women along with their rights, power and equality. As a result, its creator, Gabrielle ‘Coco’ Chanel is arguably the most iconic fashion designer of all time.

As such, these chic and sophisticated bags are now seen as a symbol not just of style savviness, but of strength, too. When you see a woman strutting her stuff with the latest model, you just know that she’s a powerful force to be reckoned with.

chanel handbag
When it comes to the most coveted luxury designer handbags in the fashion world, few houses have ever got it quite as right as Chanel. Image credit: Joe Seer/

Over the decades, Chanel has rarely failed to pull yet another show-stopping model out of the bag for the season ahead, but many of its most beloved bags remain those from times gone by. Sometimes, the older models are the most iconic – so all the more reason to collect them all.

Taking you on a journey back through time, the experts at Vestiaire Collective – the leading global platform for desirable pre-owned fashion – have selected five of the most iconic Chanel handbags of all time that are worth investing in.

Chanel 2.55

As Chanel bags go, the 2.55 has got to be the one that has made the biggest name for itself. Launched back in February 1955, it caused quite the scandal at the time. The first women’s bag that came with a shoulder strap, it was seen as a sign of rebellion. Suddenly, women had free hands, as they never had done before – which might not seem like much, but at the time, it was symbolic of the increasing equality women had been fighting for.

Despite being the oldest model on the list, the 2.55 is still beloved of many a fashionista until today, and in recent years, Sarah Jessica Parker, Blake Lively and many other A-listers have been seen sporting it as the finishing touch to a beautifully stylish outfit.

With her trademark suits and luxury handbags, fashion designer Coco Chanel created timeless designs that are still popular today. Image credit: v74/

Chanel Classic

Given its name, it was always going to be a classic, and this beautiful model – also known as the 11.2 – was a 1980’s update of the 2.55 that added some glamorous flair to this already iconic bag. The updated lock, for the first time, featured the now instantly recognisable CC logo – courtesy of Karl Lagerfeld. An update that would cement the brand’s identity for years to come, it was a significant milestone in Chanel’s journey through the ages.

Once again, the Classic remains a staple amongst the fashion elite – you only have to go to a red carpet event to see more than one or two.

Chanel Grand Shopping Tote

The Grand Shopping Tote is an unusually roomy model for the Chanel brand, and as such, fast became one of the most popular choices amongst women with a lot to carry. The ultimate daytime choice, it was sadly discontinued in 2015 – making it an even more coveted model on the fashion scene.

The bag shot to fame in the early 2000s, thanks to the likes of socialite Paris Hilton and The Hills star Heidi Montag. Today, it’s a rare vintage find, making it an instant no-brainer buy for anyone in the know.

chanel shopfront london
Chanel specialises in haute couture, ready-to-wear, beauty, fragrance, and luxury accessories. Image credit: chrisimages/

Chanel Wallet on Chain

Referred to by insiders as the ‘WOC’, the small yet spacious ‘Wallet on Chain’ bag is a chic yet practical essential for those who have a fair bit to carry but are unwilling to compromise on style. The WOC is just the right size to hold all of those important items whilst remaining inconspicuously conspicuous and rigid.

Chic and sophisticated, the likes of Eva Longoria and Keira Knightley are both fans – and it certainly isn’t hard to see why.

Chanel Oh My Boy Graffiti Bag

A departure from Chanel’s usual minimalistic designs, the Oh My Boy bag, launched as part of the A/W 14 line, was a rebellious and risky creation, and the brainchild of daring designer, Karl Lagerfeld. Taking a felt-tip pen to create graffiti prints and fun embellishments to add a little bit of punk rock edge, it was the perfect piece for its time.

Designed for the edgier dresser who isn’t afraid to break the mould, it remains a fashion world favourite until today.

Whatever Chanel turns its hand to ultimately turns to gold, especially when it comes to handbags. Any purchase is certain to be a savvy investment, and will no doubt become an icon in years to come.