Freelance Underwear Jobs in Chicago, IL (NOW HIRING)

Shinesty is a fast-growing apparel brand known for bold prints, irreverent humor, and products that don’t take themselves too seriously. Our creative team develops everything from iconic underwear prints to unexpected collaborations, and we pride ourselves on building products that are both clever and dangerously comfortable. Our mothers don’t always approve of what we do, but the millions of people we’ve entertained over the years do.

Shinesty is looking for a highly creative, humor-forward Head of Print Design to lead our print program. This person is the creative force behind some of the most memorable underwear, socks, and apparel on the internet — and they bring equal parts taste, humor, and hustle to every project.

On any given week, you might be concepting a Wienerschnitzel collaboration, brainstorming x-rated print ideas, developing kitschy gift-worthy sock collections, or pitching a limited edition collab. You'll need to hold a lot in your head at once — trends, brand voice, humor, product constraints, deadlines — and make it all look effortless on the product.

This is a true player-coach position. You'll be designing alongside your team while also leading them — setting the creative direction, managing timelines, giving feedback, and making sure the work stays sharp from concept through production. You bring the vision, you build the culture, and you're not above rolling up your sleeves to get it done.

Requirements

• Lead seasonal brainstorms across print, graphics, fabric, and design trends — spanning inline, wholesale, collabs, and limited edition
• Research competitive and aspirational brands to keep Shinesty's creative output sharp and relevant
• Identify and pitch new print techniques
• Bring fresh, culturally-aware print concepts to the table every quarter

• Design across all categories - everything from ski, formal, hats, socks, tees, knitwear, but with a focus on underwear
• Build custom repeats, reduce color artwork, and deliver production-ready files in Illustrator
• Collaborate with the Design team on solid color assortments, novelty treatments, and silhouette development
• Delegate work across the print team strategically to hit deadlines without compromising quality
• Concept and manage artwork for limited editions, retail and wholesale initiatives.

• Manage, mentor, and motivate a small print design team — setting clear priorities and a high creative bar
• Run print design reviews with the broader team; gather feedback and drive revisions efficiently
• Manage the bi-weekly Sprint Board and hold regular team syncs to keep priorities clear and momentum high
• Partner with Merch and Ops to improve process and reduce errors across product development
• Identify smart opportunities to utilize AI, bring in freelance/VA where it adds capacity

• 5-10+ years of print or textile design experience in apparel or consumer products
• Deep expertise in Adobe Illustrator — repeats, color reductions, and production files are second nature
• Extremely strong in curation and taste
• A genuine understanding of trend forecasting — you know what's resonating before it peaks
• You have a sense of humor and a real appreciation for what makes Shinesty's brand tick — you get the joke and you can make it better
• Proven experience leading or mentoring a design team while still being an active contributor
• Strong project management skills — you can hold a calendar, run a meeting, and give direct, constructive feedback
• Comfortable working across multiple product categories and channels — DTC, wholesale, collabs, and retail
• Experience with licensed collaborations, novelty product, or private label is a plus

You'll have genuine creative ownership at a brand that rewards bold thinking and values craft. Shinesty makes product that people genuinely love — and talk about. If you want to lead a team, design prints that end up on hundreds of thousands of people, and work somewhere that takes humor seriously as a creative discipline, this is the right seat.

Benefits

THE GOOD STUFF

• Relocation budget available (to Denver/Boulder), but not required
• Competitive salary plus bonus potential
• Laptop and whatever other equipment you need to entertain the people
• Medical, dental, and vision insurance
• Flexible PTO, no need to accrue time, take as much as you'd like
• Flexible working hours, just get your stuff done and generate results
• All the tools and resources you need to be successful in this role