About this stencil
This free Cool Dude Sunglasses pumpkin stencil is a printable PDF pattern you can print at home, tape to your pumpkin, and trace. A cartoon face with swept-back windswept hair, heavy brow, and large wraparound sunglasses fills this hard halloween pumpkin stencil, the lenses, hair wisps, and facial contours all rendered as separate cut sections connected by thin skin bridges. Lit from inside, the open sunglasses lenses glow brightly while the raised brow and cheek lines stay solid, giving the face a streetwise, sunlit look in reverse. The thin strands of hair near the temple are the most fragile bridges, so cut them after all the larger facial sections are removed. Use it as a carving template for your Halloween jack-o'-lantern. It is rated Advanced. Actual time varies with preparation, pumpkin size and experience. Fine details and narrow supports need careful planning. Follow the cutting and shading key in this designβs PDF.
Pumpkin size guide
- π Small (5 to 7"): print at 80%
- π Medium (7 to 10"): print at 100% (recommended)
- π Large (11 to 13"): print at 130%
- π Giant (14"+): print at 150% on tabloid paper
Frequently asked questions
Can I resize this stencil?βΎ
Yes. The PDF is vector so it scales cleanly. Print the pattern at 100% for a 7 to 10 inch pumpkin, 130% for 11 to 13 inch, or 150% for a giant. Use your printer's "Fit to page" or "Custom scale" setting.
What kind of paper works best?βΎ
Standard 20 lb letter or A4 printer paper is fine. Heavier paper is harder to bend around the pumpkin curve. If your printer supports it, set the quality to 'best' so the lines are crisp.
How long will the carved pumpkin last?βΎ
Usually 5 to 10 days. Coat all cut surfaces with petroleum jelly and store the pumpkin somewhere cool overnight. Avoid direct sun. Battery LED pumpkin lights produce no heat and help it last longer.
Can I sell pumpkins carved with this stencil?βΎ
Yes, the carved pumpkin you make is yours. The license covers personal and small-scale commercial carving (selling carved pumpkins, photographing them, posting on social). You may not resell the PDF file itself.
What if my printer doesn't print the whole stencil?βΎ
Set 'Page scaling' to 'Fit' in the print dialog and uncheck 'Auto-rotate'. If it still cuts off, the design includes 0.25" of safe-area margin so a small crop won't ruin it.
How to carve this stencil
- Start with the large open sunglass lenses, cutting each one in a single smooth pass to avoid jagged edges on the rims.
- Carve the open brow region above the glasses, leaving the swept hair strands as intact skin bridges.
- Remove the open cheek and chin contour sections on each side of the face.
- Cut the small ear and side-face detail pieces, working inward from the outer edge.
- Finish with the individual hair-wisp strands at the temples, slicing each narrow strand from its tip toward its root to prevent tearing.
Tools you'll need
For a advanced carve like this you'll want a fine-detail pumpkin saw, spoon / scoop, pin transfer tool, and small gouge if the pattern includes shading. Here's the kit we reach for, but start with whatever you already own.

Elmchee Pumpkin Carving Kit
13-piece kit with carrying case
Saws for the larger cutouts, plus a scoop for hollowing. Covers both jobs in one kit.
View on Amazon β
HOME MOST LED Pumpkin Lights
4-pack, battery operated, with remote + timer
Orange glow made for jack-o'-lanterns. The remote and timer light the pumpkin every evening without reaching inside.
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Speedball 4131 Lino Cutter Set
Handle + 5 interchangeable cutters
Interchangeable cutters for peeling and shading the face. Useful for the finer details.
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