I think the original Xbox looks great. It actually has a design element in mind. Yet the PS2 that generation was seriously an ugly, shapeless lump of black plastic and it somehow gets a pass.
Yeah, if you can't tell, PS2 gets my vote. Fantastic game library, ugly console.
Not a fan of the look of the Atari 2600 Jr., either. It's the rainbow logo, and the silver that always looks a bit tarnished by this point in time.
Oh, and the TurboGrafx-16. While it's library is damn underrated, the console itself looks like a shapeless, ugly black lump of plastic like the PS2.
Gotta say, I've always thought the Saturn looked quite handsome on a shelf, though.
I'd agree that the PS2 looks boring but I've always liked it. One thing that Sony continues to do is push for standing their consoles on their side. I've NEVER been fond of that and think they look dumb like that.
The original Xbox design was simple enough though I thought it looked silly when paired with a Duke controller. The Controller S was a HUGE step in the right direction. I think the original model XB360 looks worse than the OG Xbox, especially with the detachable HD on top. The redesign wasn't much better though I almost got in when they put out that Star Wars R2-D2 version.
For me, the least attractive systems would be the Intellivision and the wood-grained Atari 2600. The Colecovision with the controllers popped out isn't anything to look at either. Its "competition" the Atari 5200 is a hideous looking thing as well.
The reason we got that lump of plastic that is the TG-16 and not the super sexy looking PC Engine was because of FCC regulations at the time or so I'm led to believe. It didn't look nearly as bad once it was hooked up to the CD-Rom + Interface Unit though but it could never be as sexy as the PCE+CD-ROM+IFU.
As far as the Saturn goes, I prefer the solid black (with round, not oval, buttons) to the white w/colors or the grey. The original US controller is an abomination though. The only console that Sega made that I didn't much care for the look of was the original Master System. It wasn't the worst but didn't seem as well put together as the NES. They made up for that though with the Power Base Converter which looked awesome when hooked up to the Genesis. A Model 1 Gen + Model 1 Sega CD + PBC is a beautiful sight.
Not sure which handheld/portable I'd give the "award" of least attractive to. Probably the Virtual Boy though it wasn't really a portable.