Amidst capital-H Heritage’s brooding, manly-man lookbooks and too serious selfies, The Hill-Side is a bright, vibrantly patterned reminder that dressing can – and should be – fun. As anyone who owns one of the co.’s US-made ties, scarves or pocket squares can attest, H-S has a way of imbuing a sense of playfulness in their products that few other labels do. And yet, they aren’t novelty goods. The brand’s output is as solidly constructed as it is unique and unexpected; they’re pieces you can, and will, wear for years to come. And now, the Brooklyn-based label is turning its sights to apparel. Later this year, The Hill-Side will be releasing an expanded menswear collection, which includes shirts, jackets, sneakers and more.

H-S cofounder, Emil Corsillo, recently took some time out to discuss the new collection over email. Here’s what he had to say.

Well Spent: You’re expanding the Hill-Side collection to include shirts, jackets, shoes, hats, leather goods, bags and more. What led to the decision to move beyond ties and pocket squares?
Emil Corsillo: People have been asking us, “when is The Hill-Side going to make clothes?” since our very first season. Over the past 4 years we’ve kept our primary focus on fabric research and business development, and in the meantime we’ve produced a wide range of garments and accessories outside of our focused seasonal collections, in the form of collaborations with our favorite brands. But at some point it started to feel like we’ve built a brand that’s cooler and bigger than the actual range of products we produce each season. Like we were overdue for a growth spurt.

We run Hickoree’s and The Hill-Side under one roof, and we’re always balancing the needs of both – it’s like having twins. Two years ago, I was really focused on the project of bringing hard-to-find, I-can’t-believe-how-dope-this-is Japanese brands to Hickoree’s. I spent a couple of weeks in Japan with our Japanese business partner, meeting with designers of awesome brands like Freewheelers, Kaptain Sunshine, Waste(Twice), and Colimbo. That trip was incredibly inspiring, and I came back to New York full of big ambitions for The Hill-Side.

But it’s taken more than just inspiration to get The Hill-Side to the expanded position it’s in now. It required a bit of a reorganization of the company, in order to refocus enough time and money away from Hickoree’s and back to The Hill-Side.

Why did you choose to make those specific products? Were there any items you wanted to make but couldn’t?
I have a really long list of all of the things I want to see The Hill-Side produce, and it keeps getting longer. I’ve been taking a real “why not?” approach to the process. Why can’t The Hill-Side make sneakers, tailored jackets, and iron-on patches? As we started working on early designs and talking to factories, the list started to get shorter. For these first two seasons of expansion, we’ve ended up focusing our new product development based on the capabilities and expertise of our factories.

Some product ideas naturally “drop-off” in the development process. We sampled some awesome zip pouches with beautiful brass hardware, but we can’t get them made at the right price, so they’re on hold for now. Other product ideas mutated and improved during the development process. I wasn’t happy with our design for an all-fabric billfold wallet, so it didn’t make it into our Spring 2014 collection. But now we have an even better leather-and-fabric wallet coming out in the fall. I spent a lot of time last spring searching for the perfect shape for a classic Panama hat. We missed the deadline for the spring season with that product, but had it all figured out when it was time to make wool felt hats for Fall 2014.

Tell us about the design process. What separates The Hill-Side’s clothes from other brands’?
When we started The Hill-Side, the design process began with a search for a set of great fabrics. Every season we worked with the best mills and weavers to find the very best colors, textures, and patterns. It’s always really fun to lay out fabric samples on our big work table and pull together a seasonal palette with just the right mix.

We’re still hunting for and designing new fabrics, but now we start with the fit and construction details of a new product. Getting these elements right is fascinating, laborious, and gratifying. Once we feel we’ve established our archetype – our shirt, our jacket, our sneakers – we get to figure out which fabrics suit which products, and how they all hang together as a collection. Now there’s a product-fabric feedback loop: I wanted to make pointed ties out of Donegal Tweed this season, and once they were part of the collection, I realized that the fabric was amazing on a pair of sneakers.

I think the two things we really have going for us when designing clothing are 1. our uncommon talent with fabric sourcing and 2. the fact that we’ve been running a multi-brand store for the past four and a half years. You won’t find another collection of shirts, comparably priced, made in the US, in the range and quality of fabrics we offer. And running Hickoree’s has given us an eye for construction quality, fit, and trim details, and an ability to design a wearable, everyday product that still feels special and unique.

What can we expect in terms of pricing?
Well-Spent hosted a great discussion about pricing a couple of years back, and all of the those points still ring true.

We want to make the very best stuff, and we also want to make things accessible to all of our customers, and it’s tough when those two goals clash. We design and develop products with a final retail price in mind, and if we can’t make that work, the product gets dropped. We recently moved production of our five- and six-panel caps from Japan back to a small factory in Brooklyn to bring down the price.

In the fall, our shirts will start at $175 and go up to $225. Our tailored jackets will range from $395 to $500. We intentionally set up price tiers within one product offering, based on the fabric we use. This helps customers by offering them several options, and it’s also an exercise in transparency and education. We want our customers to look at our prices and understand that a wool blanket stripe fabric costs more than a selvedge, indigo-dyed fabric, which in turn costs more than a wide-loom cotton herringbone.

Our pocket squares usually cost around $40, and ties and scarves are typically in the $80 range, depending on the fabric. In the fall we’re very excited to introduce a range of solid-color, overdyed oxford fabrics that will be dramatically less expensive: $25 for a pocket square and $55 for a tie. On the other end of the spectrum, we’re also making luxurious Donegal Tweed ties at a higher price point of $145.

In order to produce the new items, you had to establish a new supply chain. Can you tell us about the factories you’re working with, and why you chose them?
In the past year we’ve added seven great new factories to our “roster.” Although it’s a lot more work, we love managing and developing these relationships. We’re working with two very new, small factories in our old neighborhood of Bushwick, Brooklyn. Our wool felt hats are made at a great place in Pennsylvania. Our vulcanized sneaker factory in Japan is one of the most legit, inspiring places we’ve ever visited. All the way down to the guy who makes our fabric-covered pin-back buttons in LA. He usually makes merch for punk and emo bands, and we asked him if he could run fabric through his machine and now we’ve got something new to spiff up your jean jacket.

You’ve collaborated with a number of apparel brands over the years. Now that you’ve got your own line, what’s going to happen to those partnerships?
As The Hill-Side has grown and developed over time, our point of focus has become more and more about the fabrics we use. Because we are known as much for our “raw materials” as for the finished products we make, we’re always in a great position to collaborate with other brands. Even though we’ve expanded The Hill-Side’s seasonal collection to include garments and a wider range of accessories, there’s still, and always will be, a world of possibilities for us to work with our friends on collaborative projects.

In the spring, we’re working with the Japanese wing of Ohio-based bag factory Drifter to produce a collection of bags made with The Hill-Side fabrics. They’ll be available in Japan and at Hickoree’s. We’re also doing another collaborative line of shirts this spring with Japanese retailer Journal Standard, featuring incredible hand-woven indigo fabrics from a crazy Japanese source.

We had a wonderful time last year working with the Institute of Contemporary Art in Boston to make a series of screenprinted Barry McGee bandanas to accompany his retrospective at the museum, and we’re planning some more exciting artist collaborations with the ICA now.

You guys are self-proclaimed fabric nerds. Are there any new textiles you’re using this year – for clothes or ties – that you’re particularly excited about?
We’ve been making our “Old Virginia” Broken Herringbone fabric for the past few seasons with a single color yarn in the weft and wild, multicolored warp. For SS14 we’re using only solid navy yarn in the warp and a single color in the weft. It makes the Old Virginia fabric look dramatically different, and it really brings out the intricacy of the weaving pattern.

For AW14 we designed a print that riffs on a print from our previous season. I grabbed a scarf in our SS14 “Big Crazy Floral Print,” xerox’d it at Kinko’s repeatedly, and then re-assembled and colored the photocopied images. The result is a floral print with big offset dots, and we call it “Xerox Floral Print.” It comes in in navy, camo, and day-glo colorways, and makes an amazing 5-panel hat.

Also for AW14, we developed a custom woven fabric with a great textile mill in Pennsylvania. It’s a basic 1-over-1 plain weave, with brown yarns in the warp and indigo yarns in the weft – we call it, plainly, “Indigo/Brown Plain Weave”. The result is like a chambray, but with two tonally similar colors that really vibrate off each other. Depending on the light or the angle you look at it, this fabric can look brown, blue, or even purple. We made a tailored jacket out of it, and it’s one of our favorites.

For price and purchase info, visit Hickoree’s.