Proper Cloth’s Design Guru On Fabric, Fit And The Future Of Menswear

I fell in love with Proper Cloth at first sight. First sight of a corduroy jacket, that is. Specifically, their Olive Stretch Corduroy Waverly Jacket: understated and sophisticated, blending the rich texture of wide-wale Italian corduroy with an unstructured, unlined design. Refined yet relaxed—a versatile staple for both casual and elevated ensembles. And as I was pleased to find out, the color—that of moss on a stone wall, a green that’s grown wise—was exactly that pictured on the Proper Cloth website.

That jacket turned out to be perfectly emblematic of a brand-wide commitment to thoughtful design, refined fabrics and versatility, and the spirit of a made-to-measure dress shirt company that has evolved—quietly and confidently—into a full-spectrum menswear label.

As Head of Design at Proper Cloth, Chris Callis oversees a collection that spans sharp Italian shirting, rugged utility wear and laid-back tailoring—an evolution he’s helped steer from the very beginning. “We’ve gone from a scrappy startup hyper-focused on dress shirts to a full-spectrum menswear brand with a broad, thoughtful collection,” he says. “But the one thing that hasn’t changed is our obsession with quality and customer feedback.”

Raised by an artist father—with plenty of gallery visits as well as creative schooling—Callis gravitated toward the unique artistic expression that is fashion. “I was always drawn to the balance between creativity and functionality,” he explains. “Menswear felt like this perfect fusion—visually expressive, but grounded in real-world use.” Callis’ attraction solidified during his time at Ralph Lauren, where he interned in the neckwear department—a division close to Ralph’s own roots—and worked weekends at the brand’s Rugby store in Manhattan. “It felt like Menswear Mecca. There was just so much talent and taste packed into that company.”

After college, he helped Suitsupply launch their social media presence but was eager to move into product design. A mutual friend introduced him to Proper Cloth founder Seph Skerritt, who was looking for someone to do both sales and fabric design. “It was a bit of a leap, but the timing was right,” Callis recalls. “I knew I wanted to be hands-on with the product, and I loved the idea of helping build something from the ground up.”

Under Callis’ design direction, Proper Cloth has refined not only its tailoring but its design process. “In the early days, our focus was crystal clear—build the best dress shirt on the market,” he says. “As we expanded into more product categories, we had to learn how to be merchants as well as designers. When you’re working with a small assortment, it’s easier for a customer to understand the story. But once you have dozens of pieces in a collection, you need each one to have its own reason for being.”

That evolution and commitment to clear storytelling is visible in a sampling of some of Proper Cloth’s most recent offerings. The di Fabio Taupe Wool and Linen Basketweave Waverly Jacket blends wool and linen in a classy basketweave pattern that breathes well across seasons. The Black Merino and Cashmere Ribbed Crewneck Sweater provides both warmth and elegance through its luxuriously soft knit. The Coffee Irish Linen Dress Pant is made from premium Irish linen—a relaxed and polished look perfect for summer days. The Blue Melange and Rose California Plaid Shirt is that rare thing: an attractive all-season shirt that offers casual refinement.

The Fresco Suit, a highlight of Proper Cloth’s recently launched spring collection, meanwhile, promises excellent airflow through its tropical fresco fabric.

Callis has a few personal favorites—“I could talk about this all day,” he admits—pointing to the Reda Merino Wool Dress Shirts as emblematic of the brand’s design ethos. “They’re kind of a signature for us now,” he says. “It’s a really elevated progression from the non-iron dress shirt—smooth, naturally wrinkle-resistant, with stretch, and machine washable. This season we updated the fit, refined the interlining for a cleaner finish, and introduced some low-contrast mélange plaids and solids. It’s all about the details.”

Another highlight: the Stretch Wool & Linen Bedford Suit, a solution for summer dressing that doesn’t sacrifice structure. “We developed a wool/linen/elastane blend that has just enough linen for that summer texture, but not so much that it gets stiff or wrinkles easily,” Callis explains. “Then we cut it in our Bedford model, which works great as a full suit or broken up. The soft shoulder, patch pockets—it all gives the suit a casual refinement that feels right for warm-weather events.”

For a more rugged offering, Callis is especially excited to launch their Sedona Cotton & Linen Plaid Utility Shirts, a homage to mid-century American workwear. “We call them ‘country plaids,’ inspired by brands like Big Mac and Old Brother,” he says. “We teamed up with a small Japanese mill that uses vintage American looms, which gives the fabric this perfectly imperfect texture. We added linen to make it summer-appropriate, updated the fit to be a little shorter and more wearable untucked, and finished it with a garment wash for softness and puckering. It’s a faithful reinterpretation, but totally modern in how it feels on.”

This kind of fabric-led approach is central to Callis’s philosophy. “We believe in following the fabric,” he says. “That means finding the right mill for each job. The mill that makes our rugged utility plaids is totally different from the one that does our fine dress shirting, and that’s intentional. A mill that’s amazing at luxury shirting just isn’t going to get that vintage workwear texture right, and vice versa.”

As Proper Cloth has grown, so has its ambition. Callis sees the brand expanding its presence both physically and conceptually. “We want to become a best-in-class menswear brand. That means more retail stores, better storytelling, more visual consistency. We’ve built a strong internal design identity, but now it’s about making that more legible to the customer.”

Still, Callis acknowledges that bridging the world of custom and ready-to-wear has been one of the company’s biggest challenges. “Not everyone is ready for custom. Some people just want a great casual shirt or are skeptical that you can get something well-fitting online,” he says. “Last year we overhauled our standard sizing and size charts. It was a ton of work, but we learned a lot. What’s interesting is that being good at custom helps you get better at standard sizing, and vice versa. That’s part of what sets us apart.”

Callis’s own style, as eclectic as it is thoughtful, informs the brand’s direction. “One day I’m into countrywear like RRL, the next it’s minimalist tailoring from brands like Stoffa or Auralee. Then it might be a traditional tailoring label out of Asia like Assisi or The Anthology,” he says. “I love seeing guys who commit fully to one style, but that’s never been me. I’m more of a synthesizer, which is something I picked up from Ralph Lauren—he’s the ultimate merchant, pulling together influences and making them feel like they’ve always belonged together.”

That same philosophy—rooted in quality, storytelling, and cross-genre curiosity—continues to define Proper Cloth’s design evolution. “Ultimately, we want to make pieces that are as interesting as they are functional, and as thoughtful as they are beautiful,” Callis says. “It’s that mix that keeps us—and hopefully our customers—excited about getting dressed.”