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Today, the handbag hardly seems radical, but in 1929, it was unlike anything that had been seen before.

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February 1955 was an important month for fashion. It’s when Gabrielle ‘Coco’ Chanel introduced a very special bag, one that would become an enduring icon of the brand and something of a household name. 68 years later, the 2.55 – named after its birth month and year – continues to capture hearts and court demand, despite its exponentially rising price. For this reason, it’s also one of those elusive fashion purchases that really is an ‘investment piece’, but more on that later.

Today, the 2.55 hardly seems radical, but in 1929 – when its first iteration was released – it was unlike anything that had been seen before. Traditionally, women’s bags were designed to be carried by a top handle or as a clutch, so Chanel’s addition of a shoulder strap (inspired by those found on soldiers’ bags) was both defiant and practical, leaving the wearer hands-free and able to move without restriction – or simply able to put their hands in their pockets, as the designer liked to do. Chanel believed in the design so passionately that she reintroduced the bag in 1955, 26 years after she’d first dreamt it up and a year after she relaunched her eponymous house.

The bag itself was rectangular in shape and dressed in soft, lambskin leather, a material previously reserved for the making of gloves. It fastened via a discreet, turnlock closure, christened the ‘Mademoiselle’ in honour of Chanel’s unmarried status. In fact, practically every element represented some facet of Gabrielle Chanel’s life. There was the diamond (and later, chevron) quilting, inspired by equestrian riding coats, covers and saddle blankets; the designer had loved horse riding and racing ever since she was introduced to it in the 1910s by Étienne Balsan, a wealthy textile heir and equestrian enthusiast.

Some also conjecture the diamond-shaped stitching was Chanel’s nod to the stained-glass windows of the convent of Aubazine’s orphanage (where she spent her early years), that the bag’s burgundy lining was the same colour as the convent uniforms, and the chain-link strap resembled the key chains of Aubazine’s caretakers.

Most notably, the 2.55 had a secret pocket hidden inside the front flap, reportedly designed for the discreet storage of love letters. Certainly, Chanel was never short of lovers (and, one assumes, love letters), and is reported to have enjoyed romances with the composer Igor Stravinsky, artist Salvador Dalí, Grand Duke Dmitri Pavlovich of Russia (with whom she created Chanel No. 5), and Arthur ‘Boy’ Capel.

68 years later, the 2.55 remains largely unchanged, though it has been reimagined in three additional sizes – maxi, large, and mini – and a whole host of colours and finishes, from denim to sequins, in addition to classic lambskin and the more practical ‘aged calfskin.’ Eagle-eyed 2.55 fanciers will notice that many of the bags on resale sites such as Vestiaire Collective and 1stdibs are labelled ‘2.55 Reissue’; this was the name given by Karl Lagerfeld to the 2005 edition of the bag (an exact copy of the original), to celebrate its 50th anniversary.

The 2.55 is often confused with the Classic Flap (also more recently known as the 11.12, after the bag’s style code number), introduced in 1983 by Karl Lagerfeld as a tribute to the original. In contrast to the 2.55’s nearly logo-less Mademoiselle turnlock and all-metal chain, the Classic Flap fastens via a CC closure, its chain strap interlaced with leather. It comes in six sizes, offering slightly more variety than the 2.55, and is available in grained ‘Caviar’ leather.

The term ‘investment buy’ is one that’s bandied around, often inaccurately, but it’s an apt description of the 2.55. Its rate of appreciation has far outpaced inflation, with prices increasing considerably year on year, whether purchased directly from Chanel or on resale. According to Sotheby’s, the 2.55 was first sold for around £170 in 1955; today, it costs more than £8,500, a 200% increase since 2016. It’s the same story for the Classic Flap. Meanwhile, the resale prices generally match or exceed the face values of well-kept styles – vintage or new – and rare bags command even higher prices.

If you’re a fan of the 2.55 or the Classic Flap, you’re not alone. Kate Moss, Penelope Cruz, Janelle Monae, Katie Holmes, Apple Martin and Alessandra Ambrosio are just a few of the celebrities who have been pictured with one of these iconic quilted bags in tow, in the daytime and to red-carpet events, proving that the design transcends ages and dress codes.

The best time to buy a 2.55 or Classic Flap bag? If time travel is an option, 1990 or earlier – that’s when price hikes began to exceed inflation. The second best time to buy one? Right now. If the last 68 years are anything to go by, it is almost guaranteed to increase in value. And if you do get your hands on the hallowed bag, you can be safe in the knowledge that it has been painstakingly crafted at Ateliers de Verneuil-en-Halatte, one of CHANEL’s Métiers d’art, by artisans who have undergone at least four years of training, mastering each and every technique to bring the 2.55 and Classic Flap (or 11.12) to life. Love letters are not included with purchase, but a certain je ne sais quoi is.

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