The 10 Most Classic Designer Handbags of All Time

For those of us who can only afford to occasionally invest in a luxury handbag, choosing a classic piece is essential. Not to even mention that classic designer bags hold their value over time and never go out of style – which is probably the biggest reason to choose those over something trendy. But where exactly to look for those handbags? 

Well, start by exploring the history of the brand that interests you. Classic designer bags have typically been around for years, even decades. Basically, ask yourself, has the particular bag been in production long enough to be considered a classic (pro tip: the longer the bag has been around, the better)?

Don’t want to browse through the archives? No worries, as I’ve already done the research and compiled a list of the most classic designer handbags ever released. From the iconic Louis Vuitton Speedy to the stylish Fendi Peekaboo, you’ll find all the must-have classic designer bags in this article.

1. Louis Vuitton Speedy

Originally introduced in the 1930s under the name “The Express”, the Louis Vuitton Speedy continues to reign supreme when it comes to classic designer handbags. Introduced as a smaller version of another hugely popular Louis Vuitton design at the time, the Keepall, it features a structured silhouette made of either canvas or leather, as well as two top handles, which make the bag look really chic when carried by hand. But fear not: newer versions of the Speedy also feature a detachable shoulder strap for hands-free convenience. In fact, the version of the bag with just the two top handles was discontinued just recently.

2. Chanel 2.55

Created by Gabrielle “Coco” Chanel in 1955, the Chanel 2.55 revolutionized women’s fashion as it was the first handbag ever to feature a shoulder strap, thus allowing women to carry their handbags hands-free. Karl Lagerfeld has then redesigned the handbag back in the 1980s and called it the Classic Flap. But nevertheless, the original 2.55 bag remains one of most classic designer handbags released to date, with its quilted leather exterior, signature chain strap, and a rectangular Mademoiselle lock captivating handbag lovers till this day. Hence the reason Karl Lagerfed has reintroduced the bag into Chanel’s classic range back in 2002. Now known as the 2.55 Reissue, the bag comes available in a wide range of sizes to suit every taste.

3. Hermès Kelly

When it comes to Hermès, everyone seems to want the Birkin. But did you know that the brand’s most classic handbag is actually the Kelly? Introduced in 1920s under the name Sac à Dépêches, the bag has risen to fame in the 1950s when Grace Kelly used it to shield her pregnancy from the paparazzi. Subsequently renamed to a “Kelly”, the Hermès Kelly bag today is one of Hermès’s most in-demand styles. In fact, it’s sometimes even harder to get your hands on a Kelly than on a Birkin. But don’t get discouraged: I’ve personally heard numerous stories of people scoring a quota bag without purchase history! See how you can try your luck here.

4. Dior Lady Dior

A symbol of timeless elegance and grace, the Dior Lady Dior bag was popularized in the 1990s by the late Princess Diana who loved the handbag so much that she owned it in every single color available. Now the hallmark of the House of Dior, the Lady Dior bag is defined by a structured silhouette in the brand’s classic Cannage pattern, two top handles, as well as a detachable strap that warrants a hands-free option. Available in a wide range of sizes and materials, with special edition designs also released from time to time, the Dior Lady Dior bag is one of the most classic designer handbags on the market and a versatile choice for both casual and formal occasions.

5. Gucci Jackie 1961 Shoulder Bag

Originally called the Constance (yes, just like the Constance bag from Hermès), Gucci Jackie 1961 is a timeless classic from Gucci, reissued by the brand in 2020. Renamed after its vibrant heritage and particularly Jackie Kennedy-Onassis, who was an avid fan of the vintage style, the handbag features a classic hobo shape with a lobster clasp closure. The Gucci Jackie 1961 Shoulder Bag also comes in an array of sizes, with options available both with and without an extra crossbody strap.

6. Prada Galleria Bag

The other day, out of curiosity, I asked my friends which handbag they would choose if they could only own one designer handbag for life. And guess what the answer was? Prada Galleria! First introduced in 2007, the bag features Saffiano leather exterior, a structured design, and an overall fairly minimalistic aesthetic (really the only “loud” element of this bag is Prada’s triangle logo decorating the front), which makes it really easy to style. The classic appeal of the Prada Galleria bag also makes it a favorite among working professionals, while a wide size range ensures that there’s a bag out there for everyone.

7. Celine Classic Box Bag

Introduced in 2011, the Celine Box Bag quickly became a fan favorite. Beloved for its minimalistic aesthetic with next to no branding (just a subtle Celine logo under the flap), this bag is a dream come true for anyone looking for a low-key designer handbag that would stand the test of time. However, if you’d like to get your hands on this bag, as of now, you will have to go the pre-loved route, as Celine has discontinued the style circa spring of 2023. No need to worry though: the resale market still offers plenty of options to purchase the Classic Box Bag in an excellent condition and pretty much any size/color desired.

10. Fendi Peekaboo Bag

Introduced in 2009, the Fendi Peekaboo Bag quickly became an icon thanks to its structured yet relaxed silhouette and unique half-open design, which offers a subtle glimpse of its luxurious interior – hence the name “Peekaboo.” Whether carried as a statement piece in vibrant exotic leathers or as a refined neutral for everyday wear, the bag effortlessly adapts to any wardrobe, rightfully earning its place as a classic. The Fendi Peekaboo also comes in a wide range of sizes and interpretations, ensuring there’s an option out there for everyone.

Would you add any of these bags to your collection? Leave your favorite classic designer handbag in the comments below!