Creative & Design Director · Chicago

Directing brands. Designing product.

I’m a Creative and Design Director with 16+ years in accessories design. I directed design for 11+ licensed brands, including Levi’s, Calvin Klein, Tommy Hilfiger and Columbia, built private label for Target, Walmart and Costco, and brought 3D and AI into how the work gets made.

Chicago · Open to hybrid, remote or relocation

Trevor Wills
Trevor WillsChicago, IL

Experience

16+ yrs

Accessories design, from Assistant Designer to Senior Design Director

Portfolio

11+

Licensed brands, plus private label for six national retailers

Team

6+

Direct reports, plus 50+ cross-functional partners

3D rollout

−66%

Physical samples after the move to CLO 3D

Licensed brands

  • Levi’s
  • Calvin Klein
  • Tommy Hilfiger
  • Columbia Sportswear
  • Cole Haan
  • Dickies
  • Tommy Bahama
  • Kenneth Cole
  • Dockers
  • Red Wing Shoes
  • Guess

Private label

  • Target
  • Walmart
  • Macy’s
  • Costco
  • Kohl’s
  • JCPenney

Case studies

Leading teams through change, running a multi-brand portfolio, and turning research into decisions.

01 AI sketch-to-image workflow

Change leadership · AI adoption

Leading a Design Team into AI

2XFaster to design and tech pack samples

Piloted three AI platforms, cleared IT, Legal and Procurement, and trained 30+ designers and merchandisers to use AI in trend, concept and design work.

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05 S/S 27 trend forecast website

Trend forecasting · Built with AI

Setting Each Season’s Trend Direction

DaysTo build the trend site, down from weeks

Turned forecasting, brand partner direction, analytics and trend trips into each season’s direction, then used AI to replace hand-built decks with a live trend site.

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06 Damen + Hastings brand imagery

Brand building · Core team

Launching Damen + Hastings

Kohl’sNational wholesale partner, grown from Chicago pop-ups

Part of the small team that built RAA’s first owned brand. Named it, worked on the brand book, directed packaging and display, and helped grow it to a national partnership with Kohl’s.

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Earlier work

Hands-on design, before I led the team

Projects from my years as a designer at Randa. I drew the CADs, built the books and worked the samples, which is why I still know the details.

How I run a design team

01

Start with the brief

Customer, price point, retailer and what the brand won’t do, settled before concepts go on the wall.

02

Bring merchandising in early

Design and merchandising work through trade-offs in month one, before the calendar decides for us.

03

Write it down

Design guides and training toolkits, so the team can run a season without waiting on me.

How I build and grow design teams

Let’s talk about your team.

I’m interested in Creative & Design Director roles across apparel, accessories, lifestyle and consumer product brands. Based in Chicago and open to hybrid, remote or relocation.