I've been working on this project about 1-2 hours every morning for the last 2 weeks, and a lot of progress has been made so far. As stated previously this project uses the ESP32-PICO-D4 micro-controller. The convenient thing about this micro is that it has reference schematics online, making the actual electrical design significantly easier (Also one of the clubs I'm involved with at my university wants to use it for most of our projects, so I wanted to get a jump on understanding using it in my projects). either way the board design is completed. Here are some glam shots of the 3D view KiCad has. 

the large pads on the left side of the second image are solder pads for the TFT display (i'm going to wire those individually so the screen can be opened/closed easily In case i want to get into this for some reason. On the bottom we have 5 buttons. 3 are for actual interfacing and 2 are for reset/programming the micro controller. On board we also have a USB-to-UART IC so that this watch can be programmed and re-programmed anytime provided a micro usb cable is handy. 

Now let's talk about size, because that's really what matters here. This project utilizes a 300mAh battery for power and a LCD TFT Module from amazon. Overall i'm happy enough with the sizing for a first revision, I've prioritized flatness over width to ensure that the watch doesn't look too ridiculous. Here's a scale printout of the board with the battery in its slot. 

Overall I'm happy with the size overall (keep in mind I plan to do future revision and this is by no means the final version). When the screen is added on:

Ok so you might be wondering about that little part of the board next to the screen. That's the location of the 2.4GHz antenna for the wifi and bluetooth, and it's fairly tall (about 8mm) so to reduce overall height it lays next to the LCD screen. I'm fairly happy with this design overall, and I think that I'm going to have a lot of fun programming it. In the mean time it'll be about a week and a half before the 4 layer board comes in, until then all I can really do is wait and maybe draw up some plans.