Headwear Sr. Designer, Level II

The Digital Stronghold; Waltham (MA); Hybrid; USD 90,000 - 120,000; Full time

Job summary

Boston Scally Company is seeking a Headwear Sr. Designer to drive concept through production across hats, seasonal collections, and collaborations in a fast-paced, entrepreneurial environment.

You’ll collaborate with Product Development, Merchandising, Marketing, and manufacturing to balance creative vision with cost, quality, and feasibility; a strong portfolio and 5–10 years of experience are required.

Qualifications

• 5–10 years of progressive design experience in apparel/headwear or related fields.
• Strong portfolio showcasing creative range and attention to detail.
• Hands-on experience taking softgoods from concept through production.
• Knowledge of materials, construction, trims, embroidery, patches, screen printing, appliqué.

Responsibilities

• Develop original, on-brand headwear concepts and translate trends into commercial designs.
• Create sketches, renderings, technical drawings, colorways, embroidery concepts, patches, trims, and labels.
• Explore new materials, construction techniques, finishes, and decoration methods.
• Own designs from research through production and revisions.
• Balance creative vision with quality, cost, and production realities with partners.

Skills

Headwear design

Adobe Illustrator

Adobe Photoshop

AI tools for ideation

Concept through production

Storytelling in product

Tools

Adobe Illustrator

Adobe Photoshop

Job description

We’re Hiring: Headwear Sr. Designer, Level II

Boston Scally Company is looking for a Headwear Sr. Designer to help shape what’s next for one of Boston’s most recognizable lifestyle brands.

We’re not just making hats. We’re telling stories through product — drawing from Boston culture, New England heritage, Americana, streetwear, sport, and the people who make this place what it is.

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.

Why Boston Scally?

Because the product is only part of the story.

We’re building a brand rooted in the tough, humble, sarcastic, and unmistakably Boston spirit — and we’re looking for people who want to help shape that story for the long haul.

Our values are simple:

Own the outcome.
Move with purpose.
Speak truth, listen fully.
Learn and share.
Drop the ego.
Build for the long haul.

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.

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