First I drew a rough idea of the design on Ibispaint X. I played around with the eye expressions such as making the owl's eyes opened or closed. I decided to make the owl's eyes closed as it gives an relaxed and calming expression on the design

I tried to explore around with small details that I can add around the owl. I wanted to give it a majestic and magical aesthetic so I decided on adding moons and stars

I did the cleanup sketch in a light blue color to make it easy for me to do the linework on Adobe Illustrator.
On the cleanup sketched, I ended up making the owl's eyes closed as it is their way of blocking the extra light in daylight. They may look like they are sleeping but they are actually wide awake, which makes them look relaxed but they are secretly active. The stars helps gives off an galactic and nighttime vibes as it tells anyone that owls are not the only one who enjoys exploring and being active at night. Some people also enjoyed being productive and active when the sun is down, whether it is indoors or outdoors. We can also call those people "Night Owls".

I took a reference picture of the Hawaiian Shirt and set it into Adobe Illustrator so that I can turn it into a template. I traced different sections of the shirt and filling them with bright colors so that it is easy to distinguish the parts. 

After tracing out the shirt and color coded, I deleted the template and recolored the shirt into a navy and royal blue to represent the "dark night"

After coloring the shirt, I emailed a transparent cleanup sketch of the pattern design and set the image as a template on Adobe Illustrator. I traced out the linework of the pattern and hand draw the stars. I copy and paste the stars by pressing ALT + dragging them at the bottom right. After tracing over the lines of the design, I deleted the template and started planning out the color scheme. I wanted the colors to look cheerful and stand out but also be careful not to make it too bright for the eyes. I picked neon pink, blue and yellow as they represent some positive personality traits and bring in some expression such as yellow representing joy and cheerful, and blue meaning calm and friendly. I also made the owl baby blue and leaving the beak transparent to give some contrast between the shirt and pattern.

After completing on the pattern design, I moved onto the buttons of the Hawaiian shirt. I decided to give it a color scheme that is a little bit similar with the pattern design colors, except making it slightly green. I used the Eclipse tool to create a big circle for the base, then created four more circles on the button and added some holes by using the shape building tool. After that, I used the radial gradient tool and set the colors to multiple to make the button more realistic, and have a depth of shadows and highlights. I also added some shadows and created strings to have some attachment to the shirt. Once I finished the buttons, I added three more buttons (using the ALT key + drag) and separated them onto the front of the shirt to give them space and making it look like a real shirt.

After the details of the pattern design was done, I selected the pieces and used the pattern function to create the pattern. For the Tile Type, I decided to go with "Brick by Colum" and "3/4" option for Brick Offset. I also settled the copies by "5x5". Once I was happy with the pattern, I added it onto my swatches panel. I apply the pattern by selecting a section of the shirt and used the Appearance panel. I selected a color to fill in the section (mostly used neon colors) and changed the fill with the pattern design. Once the pattern design is added, I used the Rotate Tool to select the pattern of the panels and used the tilde key (~) to slightly rotate the patterns to make them offsetting vertically and horizontally. 

The next part that I decided to do is crating a company label for the shirt. I created a cleanup sketch of the company brand by using similar details of the pattern (the owls and stars) but making them more "tropical" and adding some slightly desaturated colors (white and turquoise). The overall design shows an owl wearing sunglasses while relaxing on the ocean (the curves under the feet, but can also be seen as their feet) and gazing upon the stars, which gives it nighttime vibes. The company name "Owl Island Inc." is supposed to be a pun for "Our island" and the catchphrase "Live the night of your live! The starts will appear through your eyes" states that anyone can have the time to relax, no matter the time of the day. We all have our own space and world to be able to relax and enjoy what we see, either during the daytime or nighttime.

After the company label is created, I added it onto the center of the back part of the shirt, below the collar. I also used the pen tool to added some shadows on some parts of the shirt to show that there are some lights casting on the shirt. I used the appearance tool to change the opacity, applied the layer to multiply and added Gaussian Blur onto the shadows to make it realistic.