A socialite and a smoker, Gabrielle “Coco” Chanel needed her hands to sip, schmooze, and apply her lipstick. The handbags of her time, however, would not allow it. Fashion dictated that they be carried by the hand or tucked under the arm. So she created the Chanel 2.55 in February 1955 and added a revolutionary strap so that she could mingle and make memories hands-free. And so began the luxury lore of the handbag that held secrets, not just cigarettes, cosmetics, and cash—oh là là. 

What’s a story without a love affair? This one has a pocket for it. Tucked under the front flap of the Chanel 2.55 is a zippered compartment for stashing secret love letters. Designed by Coco to conceal her own correspondence, the muse for this particular pocket was Arthur “Boy” Capel. 

Despite being madly in love with Coco, Capel was under pressure to marry within his own class. In 1918, he blindsided her by marrying an English noblewoman instead. Still, his clandestine affair with Coco continued… but not for long. In December 1919, just a year after his marriage, Boy Capel was killed instantly in a violent car crash while driving to see Coco for a covert rendezvous. Devastated, Chanel never fully recovered. 

Years later, when finalizing the design of the 2.55 in 1955, she created a secret zip pocket to store his old handwritten notes and secret telegrams. If you’re not engaged in a high-stakes, high-society affair, you could always use this pocket to store your daily affirmations. (Sample affirmation: Chanel is in my future.)

Spin the 2.55 around, and you’ll find another pocket packed with a tale. Cut with a small, soft, subtle upward arc, the back pocket was named after the Mona Lisa, Coco’s favorite painting. Luxury legend has it that the artisans in Chanel’s all-female Atelier noticed the curve bore an uncanny resemblance to Mona Lisa’s mysterious smile, earning the pocket its moniker. 

Peek back inside, and you’ll find yet another pocket. This one is a slide compartment designed to hold a single tube of lipstick (preferably red). For Coco, lipstick was armor. She famously said, "If you're sad, add more lipstick and attack." It’s only fitting she built a holster for it right into the bag. Next time you need a touch-up (or a pick-me-up), reach inside your Chanel 2.55. 

Red was not just reserved for lipstick in Coco’s world. At age 11, Coco was sent to the Abbey of Aubazine, the orphanage where she grew up. Her time there left an imprint in more ways than one, so much so that it has become part of the Chanel 2.55. The red is said to be the exact shade of the uniforms worn by the children at the orphanage in which she was raised. 

The burgundy lining is not the only thing inspired by her childhood at the Abbey of Aubazine. Rumor has it that the dual-chain strap on the 2.55 replicates the metal waist chains caretakers used to carry keys. Some fashion historians also point to equestrian harnesses and bridles as design influences, a connection that would only deepen as Coco’s world became intertwined with horses.

Coco’s heart led her to the diamond quilting we’ve come to know and love. In 1906, she became the mistress of Étienne Balsan, a wealthy heir and a dedicated horse breeder. She moved into his estate and took up horseback riding, noting the padded jackets worn by jockeys and the quilted blankets used on racehorses. Soon after, Coco was introduced to the world of polo matches through her other lover, Boy Capel, where she studied the quilted waistcoats and gear worn by the players. These patterns became the blueprint for the diamond quilting on the 2.55 handbag.

Despite her high-profile romances, Chanel fiercely valued her independence and never married. To honor her lifelong singlehood, the original rectangular turn-lock was given the name Mademoiselle Lock as a nod to her everlasting title.