Billy Reid on What He Loves about Chicago and His Advice for Other Fashion Designers

By Stephen Ostrowski | May 23, 2018 | Style & Beauty

The namesake behind the lauded luxury line talks Chicago favorites, menswear trends and industry lessons with Michigan Avenue.


Billy Reid (Photo: Hannah Thomson)

There’s a palpable warmth to Billy Reid’s West Randolph Street space, a congeniality not often found in the sometimes-stiff environs of brick-and-mortar luxury retail. Credit flourishes like the store’s staircase-framing photo and art wall, or the family room-familiar furniture pieces, but the hospitable vibes are in no small shortage due to the designer himself, who, in person, exudes a soft-spoken charisma consistent with the brand’s relaxed, lived-in aesthetic.

Clearly, the approachable ethos work: later this year, the multi-CFDA Award-winning designer celebrates the twentieth anniversary of launching the eponymous line (originally known as William Reid), while the West Loop store has quickly emerged as a staple on the local style circuit since opening in 2015. Similarly, Reid’s embraced Chicago, counting Girl and the Goat, Au Cheval, Soho House and Maude’s Liquor Bar as favorite spots; of Wrigley Field, he enthuses: “That’s like no other experience. That and Fenway—can’t get any better.” While in town during this month’s James Beard Foundation Awards to host his Southern Mafia Luncheon with the Southern Foodways Alliance, Reid shared what he loves about the Windy City, the importance of resilience in the fashion industry and more with Michigan Avenue.

When you’re here, are there any destinations you try to hit up, whether it’s retail or design or arts?
BILLY REID: It’s a great walking city. Chicago has always amazed me with how clean it is for a big city. When you walk around, especially towards [Millennium] Park, and around the Art Institute, it’s just so beautiful. I feel like I see something architecturally different each time I go out there.

There’s an intangible about Chicago, that's just an energy and a positive sort of attitude of the people that really comes through. It’s not something that you can put your finger on, but I feel it every time I come up here. And I’ve felt it; even 20 years ago, I came up here, and still feel that same way.

What resonates with the Chicago customer here?
BR: Well, it’s colder here, that’s for sure, and a little windier. From a product standpoint, we definitely see more of our coats, our leathers—[which] are really two of our strongest categories as a company—and tailored clothing; people in Chicago still buy tailored clothing. They love outerwear, they love leather, and that season is a little bit longer than, say, a New Orleans, where that season is about maybe three weeks.

But, from what people seem to be attracted to, or what they seem to buy, fashion is less and less regional these days. The same thing we may see here walking on Randolph Street, I’ll see somebody at the coffee shop in Florence, Alabama, wearing a similar thing….Men getting style information instantly has completely changed what you might think someone in a small-town like Florence, Alabama might wear versus someone in a Chicago or New York these days. It’s the same; I don’t think there’s really any sort of regional fashion anymore.


The interior of the West Loop store (Photo courtesy of Billy Reid)

Industry-wide, do you see the pendulum shifting in any certain direction?
BR: Yes, I think it’s definitely swinging, from a business standpoint, [to] people making less things and better things. That’s something we’re certainly trying to do: make less and make better. Seasonless, that’s the other thing: we have completely changed our development calendar. We took seasons out of the equation. Now, we look at is as product drops that hit the stores ten different times of the year and product having a longer life cycle….If you’re going to make it, why are you getting rid of it in two months? If it’s good enough to be there, keep it for the season or keep it even longer. So making a lot less things, having more product shelf life for things and less seasonal. Doesn't mean that we’re not going to make beautiful cashmere coats or things, but really trying to make things that can have at least eight-, nine-, ten-month use for the customer.

What do you have for the upcoming Shindig?
BR: We haven’t announced anything; we’re working on some really good things. It’s the tenth anniversary for Shindig. It started as this really sort of small gathering of people, and it’s turned into this big event. We keep the template of events the same and really try to let the people involved be the difference maker of it. There will be a few things different here and there. We haven’t solidified it yet, but, with the tenth anniversary, we’re really trying to bring in some people that have been there before, some alumni pieces of it as well as some new people and kind of mix that together.

We try to keep it diverse with the music, there’s a little bit of everything….Try to give them something they’re not expecting, and then give them something that they do expect. This is my twentieth year of having a collection this year so my first collection was in fall of 98, so we’ll do a sort of 20-year retrospective and a fashion show, like a full New York-type fashion show.

billy reid

A selection of looks from the brand's Fall/Winter 2018 collection (Photo: Hannah Thomson)

What else are you doing to commemorate 20 years?
BR: To commemorate, there’s definitely some merchandising parts of it: 1998 was the Year of the Tiger, so we took this tiger and did several different things—we knitted it into a sweater and into different pieces, there’s this whole thing with patches that we did. At Shindig, we’ll do a sort of retrospective with all the runway show photographs going all the way back to 1998 in a giant room and people can see all the stuff we’ve worked on. So that will be a pretty significant part of the weekend.

Any major takeaways or lessons that resonate with you [after twenty years]?
Resilience is probably one. I started in ’98, had some pretty early success, won a CFDA Award in 2001 and then had a runway show on September 10, the day before the terrorist attacks, and then I lost my business after that. We moved to Alabama, I started all over, and then, in 2008, we opened in New York City, and literally flung the doors open the day that the stock market crashed. So we had to kind of scramble and figure out what we were going to do and we got through it.

One thing I’ve learned is to be true to yourself, be true to what you believe in, I think anytime I’ve done things when I didn’t believe in it, it didn't feel as good or maybe wasn’t as successful. So I really try to work from a gut perspective, really instinct on so many things. If I had any advice for anyone it’s: trust your instincts, be ready to face adversity and be resilient and be ready to adapt to changing conditions in the market, because in our industry, change is constant. Right now we’re going through so many market changes with digital, stores are closing all over the country.

We’ve been really fortunate. Experience is an overused word, but that’s what we started as: when somebody came to the store, it was going to be like mold that experience, from a service standpoint to what they see, touch, feel. We still believe in retail and still believe in that model. Creating that really special place that gives them a reason to go shop.

Photography by: