This post may contain affiliate links.

Talking about designer handbags worth the investment is something we definitely cannot stop doing. After a long and pleasant journey of analyzing the most popular Chanel handbags, Dior bags and the most valuable Hermes bags, we decided to take another trip down memory lane in the fashion world, compiling a list of 21 most iconic designer handbags worth the investment right now.

Most Iconic Designer Handbags Worth The Investment

Whether brand new or vintage, it’s always a good time to invest in the most popular designer handbag, especially when it comes to those that held the higher fashion status during the Nineties. Accessories are (and will always be) the fashion industry’s it-items, with the designer handbags being the ultimate hottest accessory choice for any fashionista.

Given the fact that so many fashion enthusiasts are now investing in designer handbags, we decided to recap the most coveted bags right now, consequently giving you a glimpse of the current fashion market. So, here we introduce 21 of the most iconic designer handbags of all time!

1. Hermes Kelly Bag

First introduced in 1935 and renamed later in 1956, the Hermes Kelly is not only one of the most coveted Hermes bags, but the one that is worth the investment the most in the history of fashion. Hard to get (the waiting list is endless), but definitely harder to get rid of, the Kelly was renamed after American-born actress turned Monaco princess Grace Kelly, who carried it everywhere she went and is also said to have used it to hide her pregnancy.

Most Iconic Designer Handbags: Hermes Kelly Bag

2. Givenchy Antigona Duffel

First introduced in the Givenchy fall/ winter 2011 collection, the Givenchy Antigona has been reproduced in countless colors and finishes since then. It is one of the best designer handbags for those who are always looking for something simple yet practical and especially elegant. You can get this iconic Givenchy bag from Net-a-Porter.

Most Iconic Designer Handbags: Givenchy Antigona Duffel

3. Chloe Drew Bag

Here we introduce the designer bag that has been touted by countless celebrities so far, i.e. the Chloe Drew Bag! It is probably the most copied handbag in the history of high-end designer handbags, and it is not that hard to understand why! Elegant and simple, it is the timeless fashion investment everyone is looking forward to, and is available in various colors at Net-a-Porter.

Most Iconic Designer Handbags: Chloe Drew Bag

4. Chanel 2.55 Bag

Born in 1955 and reborn in 2005 thanks to fashion designer Karl Lagerfeld, the Chanel 2.55 bag is definitely one of the most famous around. Probably one of the most legendary designer handbags of all times, Chanel’s 2.55 was named after the month (February) and year of its creation and could be regarded a sort of personification of fashion icon Coco Chanel’s fashion views. If you happen to already have one, make sure to treat it like a treasure! Pick it up on Chanel!

Most Iconic Designer Handbags: Chanel 2.55 Bag

5. Fendi Baguette

Fendi Baguette is a designer bag that was made famous thanks to the TV-series Sex and the City, which can rightly be considered one of the fashion industry’s biggest hotbeds for emerging fashion designers. Fendi’s Baguette Bag is, as hinted by its name, a small pochette that elegantly sits under any arm, like a loaf of French bread.

Designed by Silvia Venturini Fendi back in 1997, it was “the first bag that was treated like a garment,” as it’s stated on Vogue by Venturini Fendi as well, and is probably one of the fashion industry’s biggest comebacks. Those who love collecting designer handbags cannot miss this one! It’s available in various finishes, sizes and colors at Farfetch.

Most Iconic Designer Handbags: Fendi Baguette

6. Legend Alexander McQueen

Alexander McQueen’s Legend has been a popular bag in the handbag world for the past few years, and will never stop charming fashionistas in the decades to come, too. It’s one of the most elegant and timeless designer handbags worth the investment, and it’s not that difficult to understand why.

Most Iconic Designer Handbags: Legend Alexander McQueen

7. Lady Dior Bag

Named after Princess Diana, the Lady Dior is one of the fashion house’s ultimate must-have handbags. Designed in 1995, Princess Diana received it as a gift from France’s former first lady Bernadette Chirac, and became an instant success as soon as the first magazine covers featured Lady Diana carrying it around. Like the Fendi Baguette, it is one of the designer handbags making the biggest comeback at the moment, hence investing in it is definitely a good idea!

Most Iconic Designer Handbags: Lady Dior Bag

8. Chanel Boy Bag

Inspired by Gabrielle “Coco” Chanel’s tendency to play with masculine leitmotifs, Chanel’s Boy Bag now comes in four sizes and is one of creative director Karl Lagerfeld’s most successful styles. Actually pretty feminine and practical, it is a win-win accessory for any outfit, whether formal or not, and is the best fashion investment especially for those who consider Chanel as the ultimate, most soigné fashion house. Get it on Chanel!

Most Iconic Designer Handbags: Chanel Boy Bag

9. Prada Backpack

Launched in 1984 by Miuccia Prada, Prada’s iconic Backpack evolved throughout the years, becoming the ultimate perfect designer backpack in 1987. When asked about the success and inspiration behind the backpack, Miuccia Prada told The New Yorker in 1990 she wanted “to mix the industrial way of doing things, with the patrimonio of the past, with the artisanal tradition.” The backpack is available at Saks Fifth Avanue.

Most Iconic Designer Handbags: Prada Backpack

10. Gucci Jackie Bag

Originally meant to be a unisex handbag, Gucci’s Jackie Bag was designed in the Fifties and then relaunched by Gucci’s former creative director Tom Ford in 1999. In 2009, it was re-relaunched as the new Jackie by Frida Giannini, with all of its versions being instant sellouts. One of the best Gucci bags ever, its name comes from First Lady Jackie Kennedy, who carried it everywhere at any formal event. Pick yours from!

Most Iconic Designer Handbags: Gucci Jackie Bag

11. Louis Vuitton Graffiti Bag

Among the most iconic designer handbags we can mention two different yet equally iconic Louis Vuitton bags, namely the Graffiti and the Speedy. The former was commissioned by Marc Jacobs and designed by Stephen Sprouse in 2000.

Jacobs described the bag’s aesthetic as “anti-snob snobbism”, and it became an instant success as soon as Paris Hilton began carrying it around along with her sister Nicky. The Graffiti is the bag that started the whole “Louis Vuitton designer handbags” craze.

Most Iconic Designer Handbags: Louis Vuitton Graffiti Bag

12. Louis Vuitton Speedy Bag

What you may not know is that Audrey Hepburn is responsible for the popularization of Louis Vuitton’s Speedy Bag. In 1965, icon Audrey Hepburn asked Louis Vuitton to create a miniaturized version of their popular Keepall travel bag that she loved so much and that she could carry regularly. Little did they know that the Speedy would become one of the most coveted designer handbags in the early ‘00s!

Most Iconic Designer Handbags: Louis Vuitton Speedy Bag

13. Yves Saint Laurent Roady Bag

First seen on the runway for the Yves Saint Laurent fall/winter show for the 2009-2010 season, the YSL Roady Bag became famous as Gossip Girl Blake Lively decided it was her favorite designer handbag. It is also one of icon Mary-Kate Olsen’s favorite it-bags, and is therefore one of the bags that fly off the shelves the soonest whenever it drops in any high-end vintage shop.

Most Iconic Designer Handbags: Yves Saint Laurent Roady Bag

14. Celine Luggage Tote

Out of all Celine handbags, the Luggage is the one worth the investment the most, along with the Celine Trapeze. Designed by legendary Phoebe Philo, who gave tote bags their luxurious turn in 2009, the Luggage was conceived as part of “a wardrobe, a practical ABC of clothes,” as Philo told The Gentlewoman, and is one of the accessory items that will always fly off the shelves the soonest in any vintage shop.

Most Iconic Designer Handbags: Celine Luggage Tote

15. Celine Trapeze Bag

A Celine handbag is always one of the best designer handbags worth the investment, especially when it comes to the iconic Celine Trapeze. Available in numerous colors, finishes and different sizes, it features a sleek top handle and distinguishable travel wings, and if you want to own one in your favorite color, be ready to pay over $2300.

Most Iconic Designer Handbags: Celine Trapeze Bag

16. Alexander Wang The Rocco, FKA Coco

Often not a big fan of accessories, Alexander Wang is ironically one of the most popular when it comes to accessory items and designer handbags. Designed in 2009, the Rocco became extremely famous as soon as the Olsens got their hands on it, often combining it with equally rock-chic outfits. Whether you like to collect designer bags or are simply a fan of glam-rock styles, this bag is the way to go! Get it from!

Most Iconic Designer Handbags: Alexander Wang The Rocco, FKA Coco

17. Gucci Dionysus Bag

Inspired by the myth and legend of Dionysus, Gucci’s Dionysus handbag is currently the one that embraces creative director Alessandro Michele’s maximalist style the most. It also celebrates Gucci’s legacy the best way possible, and is the right investment for those who don’t want to get rid of both worlds, namely Michele’s visionary and Gucci’s legendary one. You can find it online at

Most Iconic Designer Handbags: Gucci Dionysus Bag

18. Mulberry Alexa Bag

With many first ladies and princesses being the ones who inspired the fashion houses to rename their pieces during the XX century, having an it-girl as the source of inspiration for a handbag in the XXI century was a natural consequence. Designed by Emma Hill in 2009, Mulberry’s Alexa was named after icon Alexa Chung, who still carries it around from time to time.

Most Iconic Designer Handbags: Mulberry Alexa Bag

19. Stella McCartney Falabella

Stella McCartney’s Falabella is the fashion house’s most celebrated item for sure. It is also very dear to the designer herself, as the handbag was specifically created to garner respect for the environment, as it was one of the first designer handbags to be made of eco-sustainable, cruelty-free materials. It comes in different colors at

Most Iconic Designer Handbags: Stella McCartney Falabella

20. Balenciaga Classic City Bag

Balenciaga’s Classic City Bag is a designer handbag that is basically the best investment for anyone who loves to play and experiment with watercolor effects! Urban-chic, practical and elegant, it is a great investment perfect for any occasion for sure, as it combines Balenciaga’s high street allure with some of the coolest fashionista vibes of all those girls who, between the Nineties and the ‘00s, carried it everywhere.

Designed by Nicolas Ghesquière after the less famous Balenciaga The First Bag, Balenciaga’s Classic City is one of Kate Moss’ all-time favorites, and it is definitely worth owning if you are looking for something comfortable that exudes Balenciaga’s legacy.

“It was a new fresh thing, but it looked like an old, good, friendly thing,” Ghesquière explained to WWD almost two decades ago. Get it in your favorite color from Farfetch!

Most Iconic Designer Handbags: Balenciaga Classic City Bag

21. Loewe Puzzle Bag

Finally, Loewe’s Puzzle Bag is a designer handbag only true bag addicts know, but that everyone learns to love eventually. Designed by designer Jonathan Anderson, who described it as “a soft, pliable bag that moves really well”, Loewe’s Puzzle bag “came on the market when everything was structured. It’s a new language in a bag”.

Fashion designer Anderson created Loewe’s most iconic handbag after a journey through the Loewe archives, where he found an old fake-leather bag that inspired one of his fanciest items.

“I traced the lines where it had cracked off the leather, and this very abstract shape came out. I said to my assistant, ‘I think this is the bag!” he later declared, proving the beauty of the fashion industry is in the eye of the beholder, indeed. You can pick it from Farfetch.

Most Iconic Designer Handbags: Loewe Puzzle Bag

Photos via @bartabacmode