Jessie Smith

Updated: Oct 21, 2020

Owner, Trouble Making Pinstriper

Some of Jessie's work.

Have you ever heard of Pinstriping? If not, you’ve seen it!

Envision stunning automobiles both old and new adorned with linear stripes, swirly designs and vivid images in an array of colors, shapes and textures; that’s Pinstriping. In it’s origin, back in the 1950’s Pinstriping at first was an application to cover blemishes and scratches but then quickly became a well respected art form as talented professionals realized how they could manipulate the paint and create eye catching art. This not only enhances the look of the vehicle but also accentuates its curves and body.

Jessie Smith, a Massachusetts native has been in the industry for well over a decade. From a young age she was heavily involved in the arts and later attended Butera School of Art which at the time was one of the only places that taught how to Hand Letter. She always knew she had to work her own way, learn her own and find her own path. Throughout her career she has held various apprenticeships, all challenging experiences. The last being with a very prestigious business in the area where she was for about eight years.

Smith is very fortunate to have had amazing mentors that have encouraged her and cannot stress enough how having an apprenticeship has been key to her success as she was able to learn important skills, gain confidence and become who she is. She stresses the importance of “Being a keeper of the brush.” Trades and craft need to be passed on from one generation to the next and cannot get lost.

"We need more emphasis on trade schools. We aren’t allowing that creativity, that spark to happen. We are keepers of the brush. It's our responsibility to teach kids coming up, if my one brush can help a person on a path of discovery it's worth it to me.”

In January of 2020 Smith started her own business, “Trouble Making Pinstriper.” Her business offers a variety of services; Pinstripping, creating signs and logos, truck lettering and more. Along with these services she has a store front where she sells paints and various tools. Smith states, “Maybe I'm crazy for starting something during a pandemic but, if not now, if I can get through this, I can get through anything.” She also speaks of how she feels strongly for all the closing shops that have been around for many years but in chaos brings new life, new entrepreneurship. There is a renewal process that goes along with troubling times. “I can be a part of the renewal, the new economy, be part of a revitalization project.

Traditionally, Pinstriping is a male dominated industry and still remains this way. When approaching this subject, Jessie spoke more about maintaining confidence and having a strong, positive attitude rather than about colleagues treating her any different. With no hesitation Jessie said,

“I am Fiery, never been one to back down, especially if someone says I can’t do it.”

This attitude is an exact reflection on her art. It speaks for it’s own, stands on it’s own and is well respected. She is a firm believer in having your work do the talking, and representing itself. Although she has had some tribulations breaking through as a woman she says "I am a Pinstriper..DONE. I'm a craftsman...DONE."

The emphasis she creates on not being a “women” Pinstriper and only being a Pinstriper is admiral. She firmly believes gender should not be a reason that one should excel over another. One’s art, dedication and commitment should speak for itself.

"If you want respect from your counterparts in a male dominated field you need to prove you belong there. And to me sometimes that means me working twice as hard; I have to be double perfection. If you are having trouble in your male dominated field, let the work speak for itself...the cream always rises.”

Where is the future of Pinstriping headed? According to Jessie Smith, prior to the Covid - 19 pandemic, there was a resurgence of people putting their extra money into their personal pride, primarily in their motorcycles, business signs and vehicles. She doesn't seem to worry about the industry bouncing back in the future. Jessie states,

“It's a natural occurrence, Americans as a whole, we don't let ourselves get down. We always find a way to uplift ourselves and come back stronger.”

She is already seeing this happening in her own business. As unfortunate as it is, what our country (and the world) is going through, she loves that she can create pieces to help her neighbors start and rebuild their businesses. It’s what she finds most rewarding, being a part of the community. In the future she hopes to see more community oriented projects amongst Pinstrippers such as what they call, “Panel Jams”, where Pinheads meet and create art together. Everyone has different styles, backgrounds, and views on the world. At these Jams there is no talk about indifferences or on worldly matters, it’s all about the art and to Smith, that’s what’s important.

The community is more important than money; I want to have a sense of pride in my community, my art and what I give back.”

All women can learn from Jessie Smith, no matter what industry they are in, or where they are in

their lives, generally. Smith stated..

“Nothing is stopping you from creating an opportunity, you are the only person putting limitations on yourself; if you're failing, it's because YOU'RE failing.”

At the end of every day, no matter how many attempts it may take to achieve something, never stop stepping up and attempting again. You will learn and one day you will succeed.

Q + A with Jessie Smith

Q: What is Moxxi to you?

A: “Having your own creative idea and being able to run with it. If you go through the history channel and look at how they all started...ex. Hershey, you bough millions of dollars of land and dairy and you didn’t even have a Milk Chocolate recipe ready?!? That’s Moxxi! That’s when Moxxi is in full tilt, it may break me but if I made it once I can make it again.”

Q: Who is one of your role models?

A: "Karen Souza - She is a legendary Pinstriper residing in Massachusetts. Since the 1970’s she has been incredibly well respected in the industry. If you have seen a beautiful job on a truck, that’s probably her. People don’t say she is a good woman truck letterer, no, she is a great truck letterer, PERIOD.”

Q: How do you take your coffee?

A: "Daily: Drip with cream and sugar Vacation: Summer, frozen coffee, otherwise a latte. “I’m not a Pumpkin Spice girl, it’s just not my thing.”

Q: What do you think about coffee?

A: “Coffee is the official rebel drink, the life blood. Believe me, New Englander’s love their coffee.”

Written & Curated By | Krysta Kearney, Moxxi Coffee Co.


Want to stay updated on Jessie Smith and the Pinstriping Industry? You can follow her on social media at @troublemakingpinstriper. Also, stay up to date on events and festivals going on in your local communities revolving around Pinstriping!

Find her website here:

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