6 Classic Handbags Worth the Price Tag

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Last Updated on December 26, 2023 by Steal the Style

For any woman who’s ever seen Sex and the City or scrolled through a Vogue, you know the value of a fabulous handbag. It can update any look, make any statement, be something you hold forever.

Classic Handbags You Won't Regret Investing In

So, what bags are worth your investment? After all, that’s what these bags are: investments.

If you couldn’t help but wonder what those classic bags were, we list six loved and adored ones here — trendsetting handbags that’ve weathered the storm, withstood the test of time, and held their value.

1. Christian Dior Saddle Bag

This statement bag has been a fashion icon since its inception in 1999.

It features a funky but endearing shape, plus Christian Dior’s chunky ‘CD’ initials on the strap. 

The bag became popular on the runway — John Galliano’s SS2000, to be exact — and then appeared everywhere, including on the arm of Carrie Bradshaw. From there, it was adopted by style icons and fashion lovers everywhere.

It comes in leather, an embroidered option, or Oblique canvas. It also features a variety of colors, shapes, and patterns.

2. Saint Laurent Cassandra Logo Flap Bag

The Cassandra handbag has been a staple since the 60s.

The bag was named after the YSL logo designer Cassandre. He was a prominent graphic designer that had a passion for geometrical styles.

The stacked YSL monogram is the clasp to this bag’s closure. The handbag itself is relatively small, with a boxy shape and crisp edges. It features two compartments and a double curb chain that can go long, for a crossbody bag, or be doubled, for a shoulder-length bag.

3. Hermès Kelly

Many self-proclaimed fashionistas may be surprised not to see the Burkin listed here, but its Kelly predecessor is just as fabulous, if not more.

However, like Burkin bags, Kelly bags are very exclusive and rare. It takes a waiting list (a la Samantha Jones) and a hefty budget to carry this bag on your arm. 

It takes one craftsman up to 24 hours to put this masterpiece together. It’s created with luxurious skins and leathers and shaped into a trapezoid.

When Grace Kelly used this handbag to cover her pregnant belly from paparazzi, it was renamed to honor her use of it. 

4. Fendi Baguette 

If this list lends itself to anything, it’s that SATC creators knew fashion.

The Fendi Baguette was another handbag of choice for Sarah Jessica Parker’s character. In fact, it ultimately got stolen off her wrist in a seedy alleyway.

The story of the Baguette has a funny, and obvious, origin.

Designer Silvia Fendi wanted a bag that could be carried around ‘like the famous French bakery goods,’ i.e., tucked sweetly under your arm like a baguette. 

Since other bags on the market at this time were spacious and bulky, her idea was received with skepticism. The Baguette is tiny, more for show than practicality. But she pushed, and her non-conformist vision paid off. 

It was the first bag to ever go on a waiting list at department stores.

5. Chanel Classic Flap

The Classic Flap Bag has many interesting stories attributed to it.

The original Chanel Flap bag, the 2.55 (named after its date of inception: Feb. 1955), was created by Coco Chanel.

This was the year a strap was added to a purse, allowing women something conveniently hands-free. These bags clasp with a Mademoiselle lock, which is an homage to Chanel never having married.

These bags came double-flapped (interior and exterior) with an all-chain strap. They feature a burgundy leather interior and a durable quilted exterior.

In the 80s, Chanel designer Karl Lagerfield reinvented Coco’s design to give it a modern update. This bag arguably becomes even more popular than its predecessor.

Lagerfield replaced the Mademoiselle lock with the iconic, interlocking double Cs.

Classic Flaps also use only leather-woven chain straps, unlike the earlier models that featured all chain. The story behind the leather is that Coco used it during a pinch when resources were low.

If you happen to see one of these discount designer bags for cheap, it’d be wise to snag it. Rare models in like-new conditions can sometimes sell for more than their retail price, and the others hold their value. Chanel Flap Bags are a worthwhile investment.

6. Louis Vuitton Neverfull

You’ve likely seen this oversized, tote-shaped bag before.

After all, it’s one of the most famous bags from the LV collection.

The Neverfull was created to compete with the same-ish model from the Saint Laurent house. But LV is known for making sturdy, high-quality products, and the Neverfull is no different. In fact, it takes up to 45 hours to make a single one.

The reversible bag is practical and fashionable all at once. Each bag also features an attached wallet.

You can invest in a variety of colors, shapes, and types of leather. The bag comes in three sizes and three different types of leather, each with their own patterns, hues, and colors.

The bag comes in a standard design (which is honestly the most timeless) or a variety of revamped versions.

Classic Handbags for Classic Women

If you’ve ever wanted to invest your hard-earned money into a statement piece like a luxury handbag, now’s the time.

These classic handbags hold their status, becoming heirlooms.

Or, if you ever feel like it’s time to get rid of yours, you can sell it for a fantastic value. And the longer you hold it, the more valuable it becomes.