JanSport’s “Always With You” Campaign: Cringe, Candid and Comfortably Real for Gen Z

JanSport's 'Always With You' campaign showcases relatable, awkward moments with retro animations and Gen Z humor

By: Zenia Pearl V. Nicolas

What happens when a legacy backpack brand stops trying to be cool  and instead leans into awkward honesty? Jansport could have played safe but instead, they leaned into awkwardness,  nostalgia and Gen Z humor. The result? A viral campaign that felt like catching up with an old friend.

JanSport’s new campaign, “Always With You,” is proof that cringe isn’t a mistake, it’s a strategy. In an era dominated by filters, perfection, and curated personas, JanSport went the opposite direction. Their back-to-school campaign is an ode to the in-between those messy, mundane, and emotionally awkward moments that make us real. Retro animations, puppet-like characters, clunky transitions and hilariously relatable scenes of high school chaos just raw human storytelling. 

Lindsay Read, Head of Marketing, said:

“We’re still that trusted and nostalgic brand but we’re speaking even more directly in the language of our audience.”

Partnering with comedic agency Party Land, JanSport launched a TikTok-fist, outdoor-backed campaign that leaned into Gen Z’s vulnerability, offbeat humor and day-to-day truth. 

And yes, it worked. 

What the Campaign Looks Like

The campaign consists of eight quirky video spots showing JanSport backpacks supporting users in the most unremarkable, yet deeply relatable spaces:

  • A farmer’s stand
  • A packed subway
  • A bathroom stall
  • Even a moment of grieving pet

The scenes are paired with untrained actors singing intentionally unserious anthems—deadpan, weird, and relatable. The music, humor, and visuals are all intentionally low-budget, echoing what Gen Z often produces for themselves online.

It’s not aspirational. It’s emotional realness with comedic edge.

The Strategy Behind the Cringe

According to Party Land, the creative goal was to stop trying to “look like ads” and instead reflect how Gen Z already creates and consumes content; candid, vulnerable, humorous, and a little chaotic.

“When a brand leans into who they genuinely are for their customers, rather than who they aspire to be, that’s meaningful,”

said Natalia Fredericks, Creative Director at Party Land.

Why It Worked

  • TikTok-first: Designed for organic social sharing, not for broadcast polish
  • Relatable not aspirational: From people-pleasing anxiety to grief, the campaign captures what it feels like to grow up
  • Untrained actors, real voices: Ditching gloss for deadpan delivery
  • Backpacks as metaphors: JanSport isn’t just holding your stuff, it’s holding space for you

“Our mission is to be the most trusted carry solution brand, supporting individuals through all of life’s adventures,”

said Alexandra Reveles, VP of Global Brand at JanSport.

“This campaign shows that we’re always with you, even in the moments most people overlook.”

Results That Speak for Themselves

The campaign revives ‘90s-era aesthetics with puppet-like characters, awkward voiceovers and hilariously real moments like students stuffing lockers or panicking before class.

And it’s working. According to Marketing Dive, JanSport saw:

  • 385% YoY engagement increase
  • 65% spike in TikTok traffic
  • 71% rise in purchase intent
  • Their highest one-day online sales to date 

And they did it without paid influencers. The content was relatable, not aspirational. Funny, not flashy.

JanSport’s success shows that today’s youth don’t want perfection, they want truth. The more awkward and nostalgic the ad felt, the more Gen Z leaned in. And in doing so, JanSport didn’t just sell backpacks, they sold relatability. 

This isn’t just clever marketing. It’s a reminder that behind every shared laugh is a human moment—nostalgic, imperfect and deeply felt. 

In a scrolling world of glossy content, JanSport dared to whisper: It’s okay to be real. To laugh. To feel.” and Gen Z didn’t scroll past, they leaned in. 

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