How to Draw the Monopoly Man: Easy 10-Step Guide

Bring Rich Uncle Pennybags to life with this fun, screen-free drawing activity perfect for ages 6 and up. All you need is a pencil, an eraser, and a piece of paper to master this iconic board game character. Follow our teacher-tested steps to build confidence and improve your character-sketching skills.

10 Steps

🎯 Final Result

A colorful, finished illustration of the Monopoly Man standing with his cane.

Step-by-Step Instructions

Step 1: Sketching the Face and Mustache

Close-up sketch of the Monopoly Man's eyes, nose, and signature mustache on white paper.

Start by drawing two small circles for the eyes with curved arches for eyebrows. Add a 'C' shape for the nose, then extend lines outward to create his iconic bushy mustache using a wide 'W' shape. Teacher's Tip: Keep your pencil pressure light here so you can easily adjust the mustache shape if needed.

Step 2: Defining the Head and Arms

Outline of the Monopoly Man's head, ear, and arm positioning.

Draw a large, rounded shape for the head, leaving a gap for the ear. Add a 'C' shape for the ear and small lines for hair. Extend two curved lines from the head to form the base of his outstretched arms. Teacher's Tip: Use smooth, continuous motions to make the head look more natural.

Step 3: Drawing the First Sleeve and Hand

Detailed sketch of the Monopoly Man's sleeve cuff and hand.

Enclose the end of one arm with a narrow curved rectangle to create the shirt cuff. Use small, overlapping curved lines to sketch the fingers. Teacher's Tip: Hands are tricky! Focus on the 'mitten' shape first before adding individual finger lines.

Step 4: Adding the Second Cuff and Cane

Sketch showing the second hand and the start of the Monopoly Man's cane.

Draw the second cuff with a tiny circle for a cufflink. Extend lines to form the other hand, then draw a 'J' shaped line extending downward to create his classic cane. Teacher's Tip: Make sure the cane line is parallel to give it a solid, sturdy look.

Step 5: Sketching the Top Hat Brim

Drawing the brim of the top hat held in the Monopoly Man's hand.

Draw a slanted 'U' shape near the hand to serve as the base of the top hat. Add curved lines to complete the fingers holding the hat. Teacher's Tip: This creates the illusion that he is holding his hat in his hand.

Step 6: Completing the Top Hat

Finalizing the shape of the Monopoly Man's tall top hat.

Build the top hat upward from the brim using curved lines. Add a rectangular band across the hat to give it that signature formal look. Teacher's Tip: Keep the sides of the hat straight to contrast with the curved brim.

Step 7: Drawing the Suit Jacket

Sketching the collar and the main body of the suit jacket.

Draw a 'V' shape under the chin for the collar, then extend long, curved lines downward to outline the sides of his suit jacket. Teacher's Tip: Ensure the jacket lines are symmetrical to keep him looking dapper.

Step 8: Adding the Shirt and Pants

Adding the shirt detail and pant legs to the Monopoly Man drawing.

Add a 'W' shape for the shirt tail and sketch the pants using curved lines and a 'Y' shape for the inseam. Teacher's Tip: Use a slightly darker pencil stroke for the pants to distinguish them from the jacket.

Step 9: Final Details and Shoes

Adding buttons and shoes to complete the Monopoly Man outline.

Add three small circles down the center of the shirt for buttons. Finish the pant legs and draw the shoes with irregular, rounded shapes. Teacher's Tip: Don't worry about making the shoes perfect; they should look like classic dress shoes.

Step 10: Bringing Him to Life with Color

The finished, colored Monopoly Man drawing with a shiny hat effect.

Time to color! Use black for the suit and hat. To make the hat look shiny, try adding a touch of blue to the edges for a highlight effect. Teacher's Tip: Use light, even strokes with your colored pencils for a professional finish.