Hermes Kelly and Birkin, Chanel 2.55, Lady Dior and Gucci Jackie bags have a few things in common: They're icons in fashion, they're mostly leather, they're associated with starlets and royalty, and if you have to ask the price, you probably can't afford one.
But you could afford a retro bag designed in the style of one of the legends. This type of bag would be fairly structured, with clean, symmetrical lines. A retro in the Chanel vein would be quilted, with a gold-chain strap. A Birkin or Kelly type would be big, with a dainty belt securing a leather flap closure. Gucci Jackie's retro is medium-size, with a front clasp and a contrast-color center panel. And a retro version of Lady Dior? Cane-patterned quilting, rectangular and a bit blingy: The original has gold letters spelling out "D-I-O-R" dangling from its handles.
(Side note: If you go for a bag that actually has "D-I-O-R" hanging from the handles and it costs $35, it's more "fake" than "retro.")
Besides the high-style yumminess, perhaps the greatest thing about going iconic-retro is the versatility. It's tough to clash with Birkin.
There are other retro looks, however, you may want to take a bit more care with.