Freelance Remote Stitch Fix Stylist Jobs (NOW HIRING)

Chicago, IL (Hybrid) | Full-Time

The Tie Bar is known for premium menswear, offering an extensive assortment of ties, accessories, and tailored essentials. Through thoughtful design and quality craftsmanship, we help customers build a polished wardrobe with confidence-your ultimate wingman for showing up sharp, stylish, and ready for any moment.

We're looking for an Associate Creative Director to lead the concepting, direction, and execution of brand and product storytelling across all consumer touchpoints, with a primary focus on direct-to-consumer channels. You'll lead a nimble creative team spanning design, copy, and visual merchandising/styling, ensuring The Tie Bar's brand is expressed consistently and compellingly across digital, retail, and physical experiences.

If you're equally comfortable art directing a photoshoot, mentoring a creative team, developing seasonal campaigns, and optimizing creative for performance, we'd love to meet you.

• Lead the development of seasonal campaigns, including concepting, moodboards, and art direction aligned with brand and customer positioning
• Direct photo and video shoots, overseeing concept development, casting, styling, and on-set creative direction
• Manage and mentor a small creative team, providing clear direction, feedback, and professional development
• Collaborate with merchandising and product teams to identify storytelling opportunities that highlight key categories and occasions
• Partner with e-commerce and marketing teams to create high-performing digital assets across email, website, paid media, and social
• Concept and oversee paid social campaigns; analyze performance and iterate creative in partnership with performance marketing
• Guide retail creative and visual merchandising direction to ensure consistency with broader brand campaigns
• Design and oversee brand assets including packaging, lookbooks, presentations, and in-store materials
• Manage relationships with external freelancers, photographers, stylists, and production partners as needed

You're a versatile creative leader who understands that great brand storytelling is both beautiful and conversion-minded.

You bring:

• 5-7 years of experience in a creative, art direction, or design role, preferably within men's fashion, accessories, or DTC lifestyle brands
• Excitement to be part of our Chicago-based team, with an appreciation for the city's creative and retail community
• Prior experience managing or mentoring creative team members
• A strong portfolio demonstrating campaign development, brand storytelling, and multi-channel execution with a focus on digital performance
• Experience leading photoshoots and content production with a refined eye for men's styling, composition, and detail
• Proficiency in Adobe Creative Suite (Photoshop, InDesign, Illustrator) and presentation/design tools (Figma, Keynote, etc.)
• Strong understanding of ecommerce best practices and performance-driven creative
• Excellent communication, organizational, and project management skills

• Have a passion for men's style, tailoring, and occasion-based dressing
• Appreciate classic design with a modern sensibility
• Thrive in a fast-paced, entrepreneurial environment where resourcefulness and agility are essential

This isn't a production-only creative position.

You'll be a key steward of the brand-shaping how The Tie Bar shows up across ecommerce, retail, and marketing while leading and developing a small, high-performing creative team. You'll own projects from concept through production, bridging digital and physical brand experiences to create a seamless, omnichannel story.

If you're energized by building brands through elevated, conversion-minded creativity, we'd love to meet you.

The Digital Stronghold is a portfolio of five brands spanning performance athletics and everyday style, including Taylor Stitch, The Tie Bar, Boston Scally, Pedal Mafia, and Glade Optics. Each brand has its own loyal community and distinct point of view, and together they cover a broad range of how men live, perform, and dress.

We are creators, builders, and collaborators. We believe in design-led thinking, thoughtful storytelling, and delivering products and experiences that our consumers truly love.

• Own the Outcome
• Move with Purpose
• Speak Truth, Listen Fully
• Learn and Share
• Drop the Ego
• Build for the Long Haul

Location: Chicago, IL (Hybrid) - on-site as needed,, with flexibility for remote work based on business needs

Travel: 10-20% (photoshoots, production, and store visits)

Ready to lead creative that moves a brand forward? Apply today and share your portfolio-we can't wait to see what you'll build.