Apple watch on the left, Pebble on the right
To get this out of the way: I have the 42mm space grey sport edition Apple Watch and I have the original Pebble (not the Kickstarter edition, the retail edition).
I was a Pebble user for almost two years, and now I've been an Apple Watch user for two and a half weeks and... (Spoiler Alert) I really wouldn't want to go back to the Pebble.
Don't get me wrong, I loved my Pebble. I wore it all day every day (and even most nights) up until the day I took my Apple Watch out of its packaging and put it on.
It's hard to tell from the photo at the top but my Pebble has some serious battle scars with deep scratches and a deep cut in the plastic on the left side, it's been with me for a lot.
It also has a weird metal link watch band which is too narrow for the watch that I put on after my original Pebble watch band broke and I didn't want to be without it for a day so I grabbed the band of an old Casio watch I used to wear back in the day and never got around to replacing it.
The Pebble has some amazing features: It lasts 5-7 days on a charge, the screen always shows something, it gets notifications, it has a ton of apps that do everything from fitness and sleep tracking to really basic games, it has a ton of watch faces (The one I really got stuck on is called "Revolution") and it has physical buttons for some controls so you can operate it without looking (something which may seem counter-intuitive for a watch).
The Apple Watch does... most of that. It gets notifications, there are already a ton of apps with watch extensions, and while there aren't any third-party faces some of the faces that Apple provided are really pretty (I'm using "Utility"). Part of me wishes there were more digital faces as years of wearing digital watches has made me slower at reading analog watches but there is something beautiful about an analog watch face.
The Apple Watch only does about a day on a charge. I tend to end even long days with about 40% left, so could probably do a day and a half but that would be kind of inconvenient to recharge in the middle of the day.
I initially thought I would really hate having to charge every day, but it turns out that just adding it alongside charging my phone is fine and I never really got into sleep tracking because if I know how poorly I sleep I'll just be kept up by the stress of that.
Actionable notifications on my watch is brilliant. Like for example getting a notification for an e-mail and if I don't really have to care about it just hit archive right away.
The watch apps for the Apple Watch are hit and miss. Apple's apps all work well, and some third party ones like Spark, Overcast, 1Password, Authy, MacID etc are brilliant but some are also completely useless. This is actually not unlike the Pebble where some watch apps just wouldn't work.
The Apple Watch has fewer physical buttons than the Pebble as it has a touch screen. I actually really like the combination of the touch screen and the digital crown for scrolling and the only instance where I think the Pebble was easier sometimes was that I could change to the next track without looking at the watch.
I never use the friends button on the Apple Watch, maybe I don't have enough friends but I just don't see the point. Hence it would be really nice if I could choose to remap that to something else or that apps could make use of it, so that is something I hope comes in eventual versions of watchOS.
Then comes the thing that everyone who hasn't had a smart watch comments on, the fact that the screen turns off when you don't look at it on the Apple watch.
I initially thought this would really bother me, but I realised after wearing the Pebble that it is actually kind of a feature. The Pebble automatically lights up the backlight when there is an incoming notification, which means it kind of calls attention to itself.
The Apple Watch does not, but rather just taps me on the wrist and then I can look at it when I want and it will only show it to me. This is actually something that is great because it makes me feel less self-conscious when receiving more personal notifications that I may not want other people to read.
I also realised that I don't care if when other people look at my watch they can't see the face of it like an ordinary watch. If they want to read the time then they can get their own watch after all...
After all that is said and you start looking at the things that aren't really easily marked up in a pros and cons tech specs table that is where I think the Apple Watch really shines.
Things like that the vibrator in the Pebble is so strong it feels like it's shaking your entire arm whereas the Apple Watch's Taptic engine is nice and gentle or that you really have to shake the Pebble watch to light it up and the Apple Watch just requires you to raise your wrist.
Combine this with that the Apple Watch looks like a piece of jewellery, the screen on it is gorgeous and the integration with iOS is much better than Apple will ever let the Pebble be and you have a pretty clear winner to me.
I do like the Pebble's "nerd retro feel" and it is a pretty cool "gadget watch", but the Apple Watch feels like a cool "real watch" that evokes similar feelings for me as wearing an Omega or a Breitling.
I do know of the Pebble Steel which do look more in the spectrum of "normal" watches, but I actually think that takes away a bit of the charm of the Pebble as then it kind of loses the "nerd retro feel" without really taking enough of a step towards the luxury sector. This kind of leaves it in an in-between area where it sadly doesn't really appeal to me at all.
In the end the Pebble kind of feels like the cheap Casio watches I wore for years when I was younger and the Apple Watch feels like a "grown up watch" which means it suits me very well at the point in life where I am at right now.