Meet Robert “Squeeze” Squillaro, New Exec At J. Press

If Robert Squillaro’s nickname isn’t already “Squeeze,” it might just be now. The menswear veteran — who attended New York’s FIT and went straight to work at Brooks Brothers in the twilight years of the mid’-’80s, working his way up to executive level — recently joined the leadership team of Onward Kashiyama, owners of J. Press (or “Squeeze” to its loyal followers). 

Ivy Style recently sat down with Squillaro to discuss his future plans for J. Press, as well as his past at Brooks. — CC

* * *

IS: I hear you recently returned from Japan. 

RS: I did, and I was very impressed with the retail scene, at least in Ginza [the upscale Tokyo shopping district]. The associates really take pride in their stores, and I saw more suits and ties than on Fifth Avenue. As for trad clothing, it’s a bit more fashion-forward, more about new twists on classic clothing as opposed to just classic. 

IS: Will that influence J. Press for the American market? 

RS: Well, when we do things like York Street or Blue, we need to make sure that it’s relevant to today’s consumer. But we also have to make sure the fit can take a wide range of customers.

IS: How do you hope to implement your taste and expertise with J. Press?

RS: My vision for the brand is to offer the best version of all the iconic items for the guy who loves Ivy League Style, from the countries they’re supposed to come from, such as the knitwear from England, Scotland and Ireland. It won’t make us the most price competitive, but we want you to wear something for 20 years.

On jackets I think the gorge and point-to-point need to be tweaked, but not made so fashion-forward that it won’t fit the regular guy. We want to make sure that the button stance and pocket placements are slightly higher, otherwise you look dumpy. These are the little things for how we’re going to tweak our model.

I think if we aim for the 45-year-old guy, we can also get the 65 and the 25. It’s almost like using a shotgun. There are a lot of guys in the mid-range who just want classic, good-fitting American style. We want to stay true to our heritage: a three-button, undarted natural-shoulder jacket. Do I think that over the past 30 years our model was the best of that? Maybe not. But when manufacturers go out of business, as we’ve seen, it’s very difficult to replicate that exact cut. When you look at how many American’ manufacturers exist now compared to 30 years ago, it’s sad. The only reason Southwick survived is because Brooks Brothers bought it. Over the past 20 years NAFTA hasn’t exactly been good for American manufacturing.

IS: You mean a government program may have backfired? What a surprise!

RS: There are hardly any fabric manufacturers left for men’s tailored clothing. So we have full duty on fabric coming into the US protecting mills that no longer exist. But if the same suit manufacturer has the garments made in Canada or Mexico, then there’s no duty on the fabric. It’s not a great situation.

But back to us, that’s now our focus: to make sure the shoulder is perfect, the lapel, and of course we were always famous for our slightly higher gorge. We may have two models, with one for the guy who wants to put a hip spin on Ivy, but we will never alienate our classic customer. Once Ivy Style is in you, it never leaves. 

IS: You use the term “Ivy” freely, and I’m not sure even I do that. It feels like an historic term, just as preppy has been watered down over time. I think it’s kind of quirky and cool if you use the term among associates. 

RS: I do, and I think there are slight nuances between it and preppy. When I use Ivy, it’s more J. Press and those fabulous brands and stores that popped about around colleges. To me, Brooks Brothers is less fun. It had always been less fun than Chipp, Fenn-Feinstein, Langrock and J. Press, because Brooks didn’t necessarily have a store on the college campuses. 

IS: The latest jackets are largely from the manufacturer called Empire, and they are improved over the previous model. But you want to refine them further?

RS: When you have a natural shoulder, your point-to-point needs to be narrower than if you had shoulder padding, because you need the wearer’s shoulder to support the garment.

IS: The market for Ivy and then prep was always driven by a combination of new converts as well as the old guard. Do you think the taste for it is still being passed down from father to son? 

RS: There’s still a little of the multi-generational legacy shoppers, but that group gets smaller and smaller. On the other hand, there are new guys looking at Ivy and thinking it’s really cool. He might take our Donegal Mist tweed sportcoat, buy it a size short, wear it with an OCBD, club tie, and grey flannels tapered from the knee, with Alden tassel loafers, and all of a sudden it looks really cool.

Preppy and Ivy overlap. Where our classic guy has fun is with his Shaggy Dog sweaters, madras pants, colorful socks, ribbon watchband or a belt with color. But he’s not wearing crazy bold suits. The J. Press guy gets fun with his casual clothes, but not his serious ones, save maybe for the watchband.

IS: That’s what was always so charming about WASP taste: the most outrageous fun clothes juxtaposed to the most conservative business clothes.

RS: I think there’s room with my customer for whimsical neckwear, You don’t want your guy coming in for shirts and suits and then going somewhere else because your ties are too serious.

IS: What are your other plans? 

RS: To get more brand awareness. We’re like a hidden gem. We need more people to know about J. Press and not just in the Northeast, from our stores in Cambridge and New Haven. That’s not easy to do without spending millions and millions in advertising. There are still many middle-aged guys who are not on social media and don’t know about us, so how do I reach them? The message will get out, but I also want to make sure our branding and stores are recognizable so when you enter a store, you get a J. Press experience. And the website should duplicate the store experience, say by showing combinations of items that the customer may not have thought of before. 

IS: But there are only a few stores. Doesn’t that happen already? 

RS: Well the New York store is different, but we’re doing some renovations to the DC store. We’re going to make it not so much more contemporary, but a little more masculine, more gentleman’s clubby, more blue and white and less beige. As for the campus stores, we’ll still keep the businesswear, but we want the front of the store to be just a little bit younger thinking and feeling. So if we open a new store, it will be more like DC if it’s for businessmen, and more like New Haven and Cambridge if it’s for younger customer. 

IS: Are you thinking of opening another store? 

RS: Not with what’s happening with the state of retail right now. But I would like to have one more in a city environment.

IS: What percentage of total revenues is from e-commerce, versus combined total retail revenue? 

RS: About 20%. It was higher until we reopened the NY store. Which has done very, very well since it opened. We’re very happy with the performance. We hope to have one evening event per month to help let everyone know we’re back on 44th Street.

IS: What do you see as the main difference, speaking heritage-wise, between J. Press and Brooks Brothers? 

RS: Brooks was more for when a guy’s parents sent him something, or when he graduated and went to work on Wall Street or at a law firm. When I started at Brooks Brothers in the ’80s, only about 12 percent of the buying was done in sportswear. They were primarily tailored clothing, dress furnishings store.

IS: What was your title when you left? 

RS: Global brand manager for men’s tailored clothing. But I’d spent time in accessories, pajamas and underwear, and gifts, so I know the brand inside and out. Sometimes I love to read comments on things like oxford buttondowns and the collar interlining, since I was there firsthand and a part of it. I stay out of it and just listen. But take the cloth, for example. It went from Anderson in Scotland, JP Stevens in the US, then to another mill, and when all of them closed, they had to go offshore and painstakingly tried to duplicate it. But to me it always went just a little bit down. They just never captured it perfectly. So when you take the interlining out, the old fabrics would hold their shape. The new unlined oxford isn’t quite the same; it’s a little lumpy, the way it lays on a tie. The current cloth might actually need a very thin interlining but not fused, so it doesn’t get that stiff, crunchy feel. 

IS: And what about the J. Press shirts? You can get an unlined collar special order. 

RS: Yes, and slightly longer. What’s key to a buttondown is actually the positioning of the anchor buttons. They need to be not too narrow, too spread, too far down nor too far up. That’s what gives you a roll. Back in the day the manufacturing wasn’t automated, so when you see old movies one side of the collar would be different. But that’s what gave it character and made it so special. 

IS: You were at Brooks right before the Marks & Spencer era. but were out from ’96 to 2010, when you were director of sales and merchandising for Southwick, but doing projects for Brooks. 

RS: Yes, I merchandised the Own Make collection. Unfortunately it didn’t come out the way I wanted. I think the fabrics were what I felt they should be, but not necessarily the fit. 

IS: I remember those jackets, and they were a weird fit. 

RS: It was a very tight, short fit, and how that happened was the whole collection came out of a collaboration with Bergdorf Goodman that never came to fruition, but we ended up doing it for a Japanese customer. So the fit was really designed with them in mind. So the initial version didn’t fit our customer. When we started to play around with it, it lost its expression as a three-buton sack, and then they pulled the plug. 

IS: Isn’t that an example that you can’t tweak patterns very much without getting a Frankenstein result. You have to create a new pattern. 

RS: Exactly. You do something here and you cause a problem somewhere else. It didn’t live, it’s intentions were great. But it didn’t resonate with the younger customer and it didn’t fit the classic customer. 

IS: You said you worked in every department and knew the brand inside and out. What is left of the ’80s Brooks now? You must have been quite surprised when you returned in 2010. 

RS: I think you once wrote in a post that you can’t condemn a brand for failing to be what it’s not even trying to be. I think what a lot of American heritage brands are trying to be is what they think is relevant to the majority of consumers today. We can’t deny that in the last 25 years Italian brands have done a fantastic job of convincing the American consumer that their product is the best in the world. What happened to the american menswear market is kiund of like what happened to the automobile market. When you’ve made it, you want a BMW, Audi or Mercedes, and a Zegna, Canali or Brioni suit. So Hickey Freeman, Paul Stuart, Oxxford and Brooks Brothers are in the position that Lincoln and Cadillac found themselves in.  

IS: Yes, but this isn’t a coincidence that Brooks happens to also be owned by an Italian firm. 

RS: No, but I think when Claudio first bought the company, he wanted to bring back the quality that M&S has let slide. But as the company, which has a lot of people and voices, tried to put luxury into it, but sometimes American luxury can only be fully understood by an American. Just like if you asked me to move to Italy or London and take over an iconic brand, I’d kind of have an idea, but it’s going to be an American’s version. You’re going to miss certain things. And when you try to get things right, you often resort to what you’re most comfortable with. But I still love the brand and it’s been very good to me and my life and I love the history. But are they doing everything from a style and country of origin perspective that I wish they were doing? No. But you can’t take the brand back to 1985. Everything’s changed.