Start by creating an ellipse using elliptical shape tool.

Press Ctrl+T. Right click the layer and select warp.

Adjust nodes to get the shape as shown.

Double click the layer to open layer style window. Apply layer style with the settings shown.

Create a couple of circles for the eye using elliptical shape tool.

Duplicate the eye and scale it down. Place it for the other side.

Create a flower 2 shape using custom shape tool.

Enable subtract form shape area form the top bar.

Create a circle over the flower shape. This will create hair of the cartoon.

Press Ctrl+T. Right click the layer and select warp. Adjust nodes so that it fits nicely on the dude's head.

Apply stroke layer style to the hair.

Duplicate the hair the layer and rotate a bit.

Create a rounded rectangle for the ear using rounded rectangle shape tool.

Move the ear layer behind the hair layer in layer palette.

Create an ellipse for the mouth using elliptical shape tool.

Enable subtract form shape area form the top bar. Create a rectangle to remove the upper half of the ellipse.

Apply stroke layer style. Rotate a bit.

Create a rounded rectangle for the body using rounded rectangle shape tool.

Select bottom nodes using direct selection tool. Press Delete.

Using pen tool create leg of the dude.

Duplicate the leg and place it for the other side.

Create arm and hand of the dude using pen tool.

Apply stroke layer style.

From layer menu select layer style>>create layers.

Merge both the layers. Erase the upper edge of the arm using eraser tool.

Duplicate the hand layer, rotate and place it on the other side.

Create nose of the dude using pen tool.

Remove the stroke of one side as we did for the arm.

Add details to the cartoon. Fill the background with a gradient.