Designer handbags worth the investment is one of our favorite topics, especially when it comes to Chanel bags. Chanel’s history is full of some of the most iconic designer bags of all time, which are undeniably worth the investment even if it is a long-awaited and hard-earned one.

Most Iconic Chanel Bags Worth the Investment

Before debuting the newest Chanel Gabrielle, Chanel (both the iconic designer and French fashion house) had been spending the past five decades releasing one must-have bag after another, leaving the other designers and fashion houses big shoes to fill. Creating a bag that is worth the investment in the decades to come, too, is no small feat for sure, and the current Chanel creative director Karl Lagerfeld knows it (his most recent Gabrielle Chanel bag was nevertheless a big success).

Following in Coco Chanel’s footsteps is, per se, probably one of the fashion designer’s hardest tasks, as her staples, accessories and bags have dauntlessly revolutionized the fashion industry forever.

History of Chanel

Born in Saumur, France, in 1883, Coco Chanel opened her first shop on Paris’s Rue Cambon in 1910 (one of the most magical places in Paris), starting out her career selling hats. Spotted down the streets of Paris wearing some of the most fashionable self-made dresses, Coco Chanel was often asked to sew the same dresses for other people too, and that is how her clothing line Chanel started less than a decade after she opened her very first shop.

Things then inevitably went on quite fast for Chanel, who launched her first perfume, Chanel n°5 in 1920 and, less than 5 years later, her now legendary Chanel suit with a collarless jacket and a well-fitted skirt.

Chanel’s bag history officially began in 1929, when Coco designed her first, ultra-iconic 2.55 prototype. However, we have to wait up until 1955 for the Chanel 2.55 bag to be launched and ready to be purchased, with the outcomes of the “2.55 craze” changing the handbag history for good. For the first time ever, in fact, it was acceptable for women of considerable social status in the Western world to carry a bag on their shoulders.

Best Chanel Bags of All Time

What happened next is a dream array of Chanel bags, among which the following are the ones worth the investment the most.

1. Chanel 2.55, A.K.A. The Original Chanel Shoulder Bag

Created in February 1955 (that’s where the name 2.55 comes from), Chanel’s 2.55 shoulder bag was modified by Coco, after her first design in 1929, due to practical reasons. “I got fed up with holding my purses in my hands and losing them,” Chanel was reported saying in Coco Chanel by Justine Picardie. “So I added a strap and carried them over my shoulder.”

This model is, however, also extremely important due to its iconic quilted leather, which is now synonymous with Chanel bags. Although there is no official reason behind this manufacturing detail, it is commonly thought to be in honor of Coco Chanel’s love of riding horses.

What many do not know is that the original 2.55 was lined in a burgundy hue, which was a reference to the Catholic school uniforms Coco wore back in the day when she was a student.

Best Chanel Bags of All Time: Chanel 2.55 Bag

2. Chanel Wallet on Chain

Also known as simply “the WOC”, the Chanel Wallet on Chain is a win-win bag. Available in a variety of styles, colors, finishes, and price points, the WOC is the most versatile Chanel bag you’ll ever own, as carrying one could be considered as the equivalent of wearing a cross-body bag, a shoulder bag, a messenger bag, a clutch, and a wallet, just all in one!

Best Chanel Bags of All Time: Chanel Wallet on Chain

3. Chanel Flap Bag

Like it is mistakenly believed by many, the Chanel Classic Flap Bag is not Chanel’s first bag and is not the disguised version of the 2.55. Introduced by Karl Lagerfeld in 1983, the Classic Flap Bag is a reinterpretation of the 2.55, which is now actually often referred as “the Reissue”. Chanel’s Classic Flap Bag comes in four sizes and, most importantly, has a double CC turn-style lock instead of a rectangular one.

Best Chanel Bags of All Time: Chanel Flap Bag

4. Chanel Boy Bag

Here we are with one of the most acclaimed Chanel bags – the Boy Bag. Introduced in 2011, meaning that it is pretty recent, Chanel’s Boy Bag was named after Coco Chanel’s lover Arthur Capel, whose nickname was “Boy.” Structured and minimalist chic, there is no doubt it is worth the investment!

Best Chanel Bags of All Time: Chanel Boy Bag

5. Chanel Grand Shopping Tote

Also known as “the GST”, Chanel’s Grand Shopping Tote is a dream come true for all those who always look for elegant yet roomy handbags. Unfortunately, the GST is one of the many Chanel bags that got discontinued by the fashion house, meaning that getting your hands on a GST is extremely hard nowadays. One of the most iconic Chanel bags of all time, the GST is inevitably the most covetable item in the secondary market.

Best Chanel Bags of All Time: Chanel Grand Shopping Tote

6. Chanel Kelly Bag

From one discontinued Chanel bag to another, here we are with the Kelly bag. Named after Grace Kelly, the Princess of Monaco, Chanel’s Kelly could bring a touch of timeless class to any work ensemble, even the most casual one. Like the Hermes Kelly, which is one of the most iconic Hermes bags of all time, the Kelly came in various sizes, among which the large one is the most requested one among the various international Chanel-addicted vintage lovers.

Best Chanel Bags of All Time: Chanel Kelly Bag

7. Chanel Medallion Tote Bag

Here we are with another discontinued Chanel bag that makes everyone run amok in the luxury secondhand stores. Neither too large, nor too small, it was named after the medallion with the signature Chanel CC logo attached to the zipper. Perfect for any occasion, if you manage to find one, make sure to keep it like a treasure!

Best Chanel Bags of All Time: Chanel Medallion Tote Bag

8. Chanel Petite Shopping Tote

If you are looking for the perfect tote bag that’s not too big, the Chanel Petite Shopping Tote, a.k.a. the Chanel PST is right for you, if you ever manage to find it, since that’s just another discontinued Chanel bag. The PST comes in a range of colors, from classic black and white to burgundy and red, can feature lambskin, caviar, metallic and patent finishes, and is a relatively affordable Chanel bag you can add to your collection of designer handbags.

Best Chanel Bags of All Time: Chanel Petite Shopping Tote

Photos via @aylin_koenig, Chanel