Halloween is approaching, and if you’re dreading the costume scramble, ditch the boring street clothes. This year, channel your inner skater with these six iconic skateboarder-inspired costumes. They’re easy to put together, using items you might already own or can snag for cheap at a thrift store. We’re talking costumes that could cost as little as $3! So, don’t be a Halloween kook; be a kook with a legendary look.
If you’re feeling creative, share your costume on Instagram with @jenkemmag and the hashtag #jenkycostumes. Let’s see those epic, hilarious, or just plain idiotic skate-inspired looks!
jenkem halloween costumes
Tom Penny: The Effortless Legend
Tom Penny’s style is all about that relaxed vibe. To truly capture it, master the squint while maintaining an air of effortless cool. Nail that and maybe, just maybe, you too can stretch your skateboarding career into an epic, never-ending European vacation.
Gear:
- Two or three XL long T-shirts
- A beanie pulled down low over your forehead
- Baggy jeans with a relaxed, saggy fit
Estimated Cost: $20
Tom Penny skateboarding
The Phelper: The Anti-Pro Skater
If your skateboarding philosophy is “never stop, never care” and you’re not one for moisturizing your elbows, then this is your costume. Bonus points if you manage to hill bomb into a cop car, though we don’t recommend it. This look is about that raw, authentic, skateboarding spirit.
Gear:
- A zip-up vest (Carhartt is getting pricey, so any industrial-style vest will work)
- Baggy jeans, the looser the better
- A white short-sleeved button-up shirt
- A sweater vest (go for punk, not prep)
- Black-rimmed glasses (not for vision, but to see through society’s lies)
Estimated Cost: $25
Cherry Clone: The Supreme Teen Dream
Missed your chance to nail puberty the first time? Now you can revisit it as a Supreme teen dream. Just remember to tuck everything in, and that includes everything. Channel that youthful, cool skater aesthetic that Cherry was known for.
Gear:
- A white T-shirt with the iconic red box logo (if you don’t have one, a red marker works wonders)
- Blue jeans, cut into capri-length shorts
- Converse All-Stars (no substitutes for this one!)
- A skinny belt to cinch your waist
Estimated Cost: $40-$60
J Cassa Nova: The Molly Man
Triple your swagger by becoming the one and only J Cassa Nova. Be warned, your rap skills might become so impressive that you’ll find yourself fending off record labels and admirers who only want you for your swag. Embrace the persona and own it.
Gear:
- A large crew neck sweatshirt
- Baggy jeans to contain all that style
- Plastic jewelry (if you don’t have any, tape a plastic gold coin to Mardi Gras beads)
- A beanie pulled up high, Smurf style
- A marker for all those face and neck tattoos
Estimated Cost: $15
Jereme Rogers skateboarding
The Muska: The One True God
Show your devotion to the skateboarding deity, Chad Muska, by embodying his iconic look. The kids will love you, celebrities might get jealous, but most importantly, you’ll love yourself. This is about more than just a costume, it’s about an attitude.
Gear:
- A red tank top with a printed TSA logo (tape a printout on if you need to)
- Swishy pants, the puffier the better
- A red hat
- As many sweatbands as you can possibly fit
- A boom box to keep the party going until those D batteries die
Estimated Cost: $40
Chad Muska skateboarding
This Halloween, don’t settle for a basic costume. Embrace the spirit of skateboarding and become one of these legends for a night. Whether you’re going for effortless cool, rebellious spirit, or over-the-top swagger, there’s a skateboarder costume for you. Now go get your skate on and have a Happy Halloween!
- Written by: Krusty Karl
- Original Illustration by: Michael Giurato
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