I'm always on the hunt for affordable favorites that only look high end. A dress, coat, or — gasp — even leather bag that instantly pulls together my look and keeps my wallet happy at the same time. That said, sometimes you just have to take a deep breath and splurge, especially when it comes to those lust-worthy handbags that I've been dreaming about since I was a child. The Chanel 2.55, Hermès Kelly, Louis Vuitton Speedy, and more . . . the history is palpable. Ahead, find the nine classic bags totally worth the investment. They'll last you forever, make your most casual jeans and T-shirt look elevated, and maybe even stand as a family heirloom for generations to come. These stunning timeless classics might cost more than your rent but, if you can swing it — just once — you definitely won't regret it.
1Hermès Kelly
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First debuted in 1892, this iconic handbag served a far different purpose than it does today, resting comfortably in the crook of the arm of half of the Upper East Side of Manhattan. Originally, the Hermès Kelly was designed as a tote for a horse's saddle in a size that, though huge, was still small enough to fit in the back of a late-century automobile. It wasn't until 1935 that it was designed in a more petite shape, called the Sac à Dépêches. Just a few years later, in the 1950s, it was Princess Grace Kelly who popularized the bag, reportedly held in front of her stomach to hide her pregnancy from photographers and the press. As such, the now-iconic handbag style was renamed the Kelly, forever linking the iconic style to one of the fashion world's most elegant of muses.
Much like the Hermès Kelly, the Louis Vuitton Speedy was initially intended as a larger travel bag. Initially named the Keepall in its exaggerated size, it fit well among the then-exclusive luggage brand from which it was designed. As demand shifted towards handbags of the smaller variety, the aptly named Speedy was born as a mini version of the original top-handle duffel shape. Though smaller it was, avid wearer Audrey Hepburn was the one who initially requested even tinier custom styles be made for her use which are, as we all well-know, now sold off-the-shelf around the world.
Perhaps the most of any other icon on this list, the classic Chanel 2.55 quilted handbag not only effortlessly spans generations, but also takes the wearer from morning coffee to best friend brunch; family dinner and late-night date alike. Named after the date in which it was created (February 1955), the chain-strap, quilted design is one of the most recognizable luxury statements in the world. At its inception, the chain was actually quite innovative, as Coco Chanel wanted a bag that the girl-on-the-go could tote around while leaving her hands free. Fun fact? The interior pocket that still exists today was practically added for Coco to stash her love letters in secret.
Leave it to Hermès to make it to the handbag icons list not once, but twice. And it is with a more casual take on the aforementioned Kelly, if you can even call a Birkin Casual. Nearly 100 years after the Kelly first debuted, the Birkin made its mark—with the help of style icon Jane Birkin. As the story goes, the actress-turned-model was seated next to Hermès Chief Executive, Jean-Louis Dumas, on an airplane in the early-1980s, expressing her need for a chic carryall handbag. What resulted from the conversation was a more tailored and everyday take on their existing oversized Haut à Courroies bag from the early 1900s. And the well-known hefty price tag comes with reason, as it takes two full days to craft a single bag, before you even start talking about all the one-of-a-kind add-ons you can opt into.
Ah, the '90s. A time where athleisure was truly born. The activewear of the 1980s mixed with the grunge of the coming decade to create a wardrobe that encompassed a newer, edgier take on the sporty look. And, for those looking for a high-end designer take on the trend, Prada made it happen with the popularization of their black nylon backpack (which was, as it were, originally introduced a few years prior in 1984). It was athletically-inspired, easy-to-wear, and depending on the size, fit everything you needed for a girl-on-the-go. In a functional move for a runway-ready collection, the bag is actually made of the same nylon that is used to create Army tents.
In an international gift of style, the popularization of the Dior Lady bag actually began when one was given to Princess Diana by the First Lady of France, Bernadette Chirac, in 1995. As such, many often refer to the style as the Princess Bag, though it was never officially re-named by the house itself. The late fashion icon might have made the top-handle tote popular in the 1990s, by way of her growing collection, but the style was actually originally introduced by Christian Dior himself almost 40 years prior, reportedly inspired by the chairs that sat the guests at his first-ever fashion show in 1947.
As modern-day icons go, this is one of the more recent additions to the list, epitomizing the early aughts by the likes of Mary Kate and Ashley Olsen, Nicole Richie, Paris Hilton, and more. One of the few bags on this list that was, right out of the gate, introduced in a rainbow of hues and multiple styles, the brand ensured that there was not only a City bag for every girl, but also the ability for collections to quickly ensue in a single style-lover's closet.
Much like the Balenciaga City, the Proenza Schouler PS1 was the stylish girl's answer to a designer bag that perfectly walked the line between elevated tailoring and understated bohemian. Named after both the brand itself in initials but also with a nod to NYC public schools, it boasts a top flap, double handles, and a cross-body strap all-in-one, ensuring that the styling potentials are endless. What's more, it also debuted in a multitude of colors, making sure that there was something for everyone. Immediately a hit upon 2008 release (though initially described as the "anti-it bag"…), it was beloved by Mary Kate and Ashley Olsen, Kristen Dunst, Jessica Alba, and more.
While Phoebe Philo is often given the honor of being called the creator of the Classic Box Bag at the French fashion house, she actually re-designed a classic from the 1970s archives. With a virtually identical shape to its predecessor, Philo did change the closure from a more intricate vintage Celine logo to a cleaner metal clasp, synonymous to her overall vision for the brand under her design. Now, this minimalist shape is available in a multitude of colors which vary from season to season and, even now that she has left the brand, still remains in constant rotation when it comes to Celine's accessories with each passing collection.
