Headwear Sr. Designer, Level II

Boston Scally Company

$80K — $95K *
Retail & Consumer Goods
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5-10 years of progressive design experience in apparel, accessories, headwear, or related fields.
  • Strong portfolio demonstrating creative range and attention to detail.
  • Hands-on experience in taking products from concept to production.
  • In-depth knowledge of materials and various decoration techniques.
  • Proficiency in Adobe Illustrator and Photoshop, with experience using AI design tools.

Responsibilities

  • Develop unique, on-brand headwear concepts that innovate and inspire.
  • Translate cultural trends and consumer insights into commercially viable designs.
  • Create detailed sketches, graphics, and product specifications.
  • Experiment with new materials and design techniques for headwear.
  • Manage the design process from research and concepting to production and revisions.
  • Collaborate with cross-functional teams to integrate feedback into final designs.
  • Oversee multiple projects and timelines in a fast-paced environment.

Benefits

  • Hybrid work model with flexible in-office requirements.
  • Opportunities for occasional travel for product development and events.
Full Job Description
We're Hiring: Headwear Sr. Designer, Level II

In this role, you'll own the creative design process from concept through production, developing unique cap designs across silhouettes, seasonal collections, core programs, collaborations, and special projects. You'll work closely with Product Development, Merchandising, Marketing, and manufacturing partners to turn big ideas into products people genuinely want to wear.
What You'll Do
  • Develop original, on-brand headwear concepts that push the product forward.
  • Translate trends, cultural influences, consumer insights, and storytelling into commercially relevant designs.
  • Create sketches, renderings, technical drawings, graphics, colorways, embroidery concepts, patches, trims, labels, and other product details.
  • Explore new materials, construction techniques, finishes, and decoration methods.
  • Own designs from initial research and concepting through samples, revisions, and production.
  • Partner with Product Development and manufacturers to balance creative vision with quality, cost, construction, and production realities.
  • Establish seasonal design direction and maintain a strong, consistent creative point of view.
  • Present concepts to cross-functional teams and confidently incorporate feedback.
  • Manage multiple projects, timelines, and priorities in a fast-moving, entrepreneurial environment.
  • Stay curious about emerging design tools, technologies, materials, and AI-powered creative workflows.

What We're Looking For
  • 5-10 years of progressive design experience, ideally in apparel, accessories, headwear, lifestyle, streetwear, footwear, or consumer products.
  • A strong portfolio showcasing creative range, commercial product design, and exceptional attention to detail.
  • Hands-on experience taking softgoods from concept through production.
  • Strong knowledge of materials, construction, trims, embroidery, patches, screen printing, appliqué, and other decoration techniques.
  • Strong skills in color, graphics, typography, proportion, textiles, and product construction.
  • Proficiency in Adobe Illustrator and Photoshop.
  • Experience using AI tools for research, ideation, and image generation - and a willingness to keep evolving with the technology.
  • Excellent communication, presentation, collaboration, and organizational skills.
  • A solution-oriented mindset and the ability to turn ambiguity into clarity.
  • Someone who is proactive, adaptable, highly self-motivated, and comfortable managing multiple projects and deadlines.
  • Most importantly: a strong creative point of view without a big ego.

Headwear experience is preferred, but we're open to designers who bring exceptional softgoods experience and the right creative perspective.
Location: Waltham, MA
Work Model: Hybrid - 3+ days per week in the office as needed, with flexibility based on business needs
Travel: Occasional domestic and international travel for product development, vendor/factory visits, trade events, photoshoots, and team meetings.

If you're a product-obsessed designer who can bring creativity, craftsmanship, commercial thinking, and a little Boston attitude to the table, we'd love to see your work.

Apply now and show us what you've got.

#Hiring #ProductDesign #FashionDesign #ApparelDesign #Headwear #GraphicDesign #BostonJobs #DesignJobs #CreativeJobs #WalthamMA

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