The Steps (1-16)
1. Create a new document 800 x 800 pixels.
2. Select the Ellipse Tool, Left-click and hold Shift to draw a circle. Give the circle no Fill, and add a Black Stroke with a Stroke Weight of 16px.
3. Next, select the Pen Tool, Left-click anywhere on the artboard, then Left-click again below and slightly to the right to create an angled line. Left-click and hold to draw a curve at the bottom – this is going to be the left half of your first tentacle.
4. Select the half tentacle, and go to Edit > Copy, and then Edit > Paste in Place, hold Shift and drag to the right. Next, go to Object > Transform > Reflect, and reflect the shape along the Vertical Axis.
5. Line both halves of the tentacle up so that they touch, and using the Direct Selection Tool, drag over the two end anchor points on the lowest part of the tentacle and go to Object > Path > Join. This will join up both halves of the tentacle into one curved line, with the top kept open.
6. Go to Edit > Copy, and select Edit > Paste in Place to create a copy of the tentacle shape. Select the Rotate Tool and Left-click on the top-right anchor point, then drag Clockwise around this rotation point so that your second tentacle is at an angle, but still joined to the first.
7. Using the Direct Selection Tool, drag over the two anchor points where both tentacles join, and go to Object > Path > Join. In the Stroke Palette you can also change the Cap and Corner type to Round.
8. Repeat Steps 4-5 to create a ‘reflected’ copy of both tentacles, so that you end up with four tentacles in total that are symmetrical.
9. Align the circle created in Step 2 centrally above the tentacles, and move all four tentacles upwards until the top anchor points on each tentacle, all touch the circle itself.
10. Select all shapes on the artboard, and in the Pathfinder Palette select Unite to combine all individual shapes into an outline of the octopus that is all one complete shape.
11. Next we’re going to create the eyes. Select the Ellipse Tool, and draw a small circle inside the head of the octopus. Using the Direct Selection Tool, delete three of the anchor points, leaving just one quarter of the circle left. Using the Add Anchor Point Tool, add a new anchor point somewhere along the remaining quarter, and then delete the anchor point to the left/right of it. The purpose of this step is to slightly shorten the remaining quarter.
12. Next, repeat Steps 4-5 to create the second half of the first eye and join the two halves together into one complete curved line.
13. Go to Edit > Copy, and select Edit > Paste in Place, and drag this shape to the right to create the second eye. Drag over both shapes and go to Object > Group, to group both eyes together.
14. Repeat Step 13, but instead drag this shape down and into the center of the octopus head. Using the Rotate Tool, rotate this shape 180 degrees to form the mouth.
15. Select all shapes on the artboard, and in the Align Palette on the right select Horizontally Align Center.
16. Lastly, give your octopus icon some colour from the Swatches Palette and you’re done!
Read More at Drawing a Vector Octopus Icon in Illustrator
from Web Design Ledger http://webdesignledger.com/drawing-vector-octopus-icon-illustrator/