Considering that Apple is currently seen as a company with impeccable design sense–that releases category defining products, you might be surprised when you look at Apple’s products released before (and in some cases, shortly after) the new millennium. Fortune magazine recently posted a retrospective about some of Apple’s design missteps; machines considered so ugly or flawed that they should not be. For fans of Apple’s enigmatic co-founder, it should be noted that only a few of the products, such as the garishly colored JLPGA PowerBook 170, was released while Steve Jobs was not involved with Apple.

The List Of Ugly Products Apple Has Released Over 36 Years

JLPGA PowerBook 170, as pictures by jimabeles on Flickr.

I don’t think it’s a perfect list. For one, while it’s not practical or stylish in a contemporary sense, I absolutely love the design of the Macintosh Portable. The 16 lb dates back to 1989, had a decent black and white LCD screen and were powered by what were essentially miniature car batteries. It’s hard to fault the early laptop in the same way that it’s hard to fault cellphones from the 1980s. The keyboard and trackball is beautiful and it looks like a classic piece of kit.

The rest of the devices Fortune got right. The eMate 300 looks like a junky toy laptop, the lackluster print on the Flower Power iMac was probably a misstep, and I have no idea what Apple’s design team was thinking when they came up with the JLPGA PowerBook 170–a strangely mismatched variation of an otherwise solidly designed portable computer.

The List Of Ugly Products Apple Has Released Over 36 Years

Say what you will about the Mac Portable in terms of pragmatics; it’s still one of the finest looking devices from 1989.

What do you think is the worst product Apple’s ever designed? The original Newton PDA? The old failure-prone iPods? Or do you really dislike the design of the iPhone 5? Share your thoughts in the comments section below.