Few brands are as deeply tied to a particular bag structure as Chanel. The legendary Coco Chanel made shoulder bags acceptably chic for upper-crust ladies over half a century ago, and the brand has been closely tied to chain straps, quilted leather and flap closures ever since. A few years ago, the Chanel Boy Bag was introduced to advance the legacy that the 2.55 Flap Bag started and the Classic Flap Bag continued.

Although the Boy Bag is a newcomer compared to the Classic Flap, it’s become so popular with customers that we have no doubt it will eventually enter into the pantheon of Chanel classics. It has the most important elements of Chanel’s signature handbag style (the aforementioned chain strap, quilted texture and flap structure), but assembled in a way that’s less delicate and formal than the flap bags that came before it. If you ever felt like the Classic Flap was too fancy or grown-up for your everyday life, the Boy Bag is a more casual, modern alternative.

On the other hand, the Boy Bag doesn’t have quite as much going for it, structure-wise. Its interior is just a single compartment lined in woven fabric, while the Classic Flap’s is lined in sumptuous burgundy leather and features several pockets and a hidden compartment for love letters. (I’m not joking–check out my roundup of fun facts about Chanel’s flap bags for more trivia.) I’ve held both, and the Classic Flap Bag just feels more luxurious to me, even though the Boy Bag is much more in line with my personal style.

The Boy Bag is less expensive than the Classic Flap, but not drastically so–the small Boy is $4,300, while the small Classic Flap is $4,900. With all those things in mind, whether I would pick the Boy or the Classic Flap comes down to which version of each I’m considering. In a hypothetical world where I’m choosing between my ideals of both, I’d probably go with a Classic Flap, but it’s a narrow win.

Now we want to hear what you think–tell us which Chanel icon you prefer in the comments!

Chanel Boy Bag
$4,300 via Chanel

Chanel-Boy-Bag

Chanel Classic Flap Bag
$4,900 via Chanel

Chanel-Classic-Flap-Bag

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