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.

48 Comments on "Meet Robert “Squeeze” Squillaro, New Exec At J. Press"

  1. Giacomo Bruno | May 2, 2018 at 3:33 pm | Reply

    In the old days, salesmen at J. Press ( and Broos, as well) would have ignored an unshaven customer, no matter how well he was dressed.

  2. Bravo. A keen, insightful, knowledgeable conversation. Break a leg, Mr. Squillaro!

  3. Mark Russell | May 2, 2018 at 3:58 pm | Reply

    Tough act to follow.
    May the force be with you.

  4. This was a nice piece. I am looking forward to see how things go for Squeeze. The new shoes made by Rancourt look really nice. So far, the rebuild is looking good.

    @Giacomo Thanks for the helpful comment.

  5. Mitchell S. | May 2, 2018 at 4:03 pm | Reply

    He uses the term “ivy” to refer to J. Press but the right term is “trad”. However, trad gets no respect. These whippersnappers today have no respect for classic traditional menswear.

  6. Roger Sack | May 2, 2018 at 4:37 pm | Reply

    Padded shoulders and a roll-less button down.
    Not a great start.
    I hope that I am wrong.

  7. @Roger Robert’s the man. Happy days are here again!

  8. Thank you, everyone, for the fine comments so far.

  9. whiskeydent | May 2, 2018 at 5:26 pm | Reply

    @Christian
    Regarding another story a while back, I raised the idea of J. Press barnstorming the country with trunk shows as they did decades ago. As I recall, I suggested that Ivy Style would be a good vehicle for spreading the word. Did anything of that nature come up in the conversation?

  10. I shall be popping into NYC later in the year, so would you please try devilishly hard to “make sure the shoulder is perfect” by then, Mr. Squillaro. My gratefulness would be unbounded.

  11. Joel Vaughan | May 2, 2018 at 6:35 pm | Reply

    His comments on the need for a lining in the old-new BB OCBD are interesting. Nice to see since I have so many of them.

  12. @Mitate For reference…what’s the closest to perfection you’ve encountered?

  13. @Roger – I know you are referring to his photo when mentioning the shoulder padding and collar roll. But I think it’s important remember that Press has made great strides in the past year re: a natural shoulder. The new Empire jackets feature a much better shoulder than the old Cohen jackets. And the Press button down doesn’t feature the full roll that Mercer and some of the new-old Brooks shirts have.

  14. I should say the Press button isn’t renowned for the roll featured on the Mercer and old-new Brooks. But a very fine shirt nonetheless. Plus they are selling a yellow shirt OCBD this season!

  15. NAFTA didn’t backfire! It achieved its purpose and resulted in reducing the price of consumer goods for American while promoting stability via economic development of our neighbors. Of course manufacturing lost out, but net positive for the U.S.

  16. Vern Trotter | May 2, 2018 at 11:08 pm | Reply

    He looks like me when I go 2-3 days sans razor. Impressive background.

  17. Great piece and will be interesting to see how things develop. It’s a challenging balance to serve the older customers while attracting the new. I think the “45 target” is very smart and if done well, the older/younger gaps are still attainable.

    “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?”

    Well, they may not be on social media, but a bet a fair number of them search on Google, and a good SEO and content marketing program won’t cost millions and millions. Mr. Squillaro, if you read this, we should talk (click my profile link).

  18. Boston Bean | May 3, 2018 at 12:17 am | Reply

    An unshaven man wearing clashing stripes on tie and shirt + a lapel pin + a tie clip + Brylcreem. Not someone I’d go to for sartorial advice.

  19. Vern Trotter | May 3, 2018 at 12:31 am | Reply

    What are the odds on cuffs ? No cuffs?

  20. I’m afraid my closest encounter won’t help as a reference, DCG. It was on a jacket by German company Oska, which I obviously had to file under ‘fluke’.

  21. S.K. Taylor | May 3, 2018 at 3:15 am | Reply

    Boston Bean,
    I’m afraid I have to agree with you.

  22. Wishing this gentleman well.
    Recommend he pays more attention to custom options than off the peg, as that is where true Ivy now is.
    I can’t see a lucrative future in ready made sub-Ivy copies unless the details, especially the shoulder line, are spot on for the Ivy buyer.
    Maybe he will capture the Ivy-Curious market or some kind of Ivy-Hybrid market?
    J. Press can produce some fine custom garments. For the Ivy buyer I would suggest that that is where their attention should be when looking at this once revered clothier.

  23. Great interview. And great insights.

    Especially appreciated:

    “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.”

    “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.”

    “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. ”

    Again, really great stuff here. Thanks for the interview.

  24. Maybe a broken record, but Gambert offers an oxford that’s vintage as hell. In a good way. Thick, beefy. Robust stuff. Calls to mind what the old (Brooks) oxford cloth must have been like. A pinch of the collar leads you to guess there’s interlining, but there isn’t. Just the cloth. It’s bed linens weight, which is all to the good.

  25. Gambert oxford reference is 5251, in case anybody’s interested. Throwback cloth. Thinking one shirt will last two decades of wearing, washing/drying, dry cleaning. Cloth with “vigah”!

  26. Just Sayin | May 3, 2018 at 9:29 am | Reply

    Interestingly, American manufacturing was departing US soil for Mexico and Asia due to cheaper manufacturing costs (usually labor rather than actual manufacturing) well before NAFTA. There are several good books on the history of US labor-management relations which offer insight into how the history of unionization and labor organization pushed US companies to seek out lower labor costs, first in the US and then outside of it. For example, while NAFTA was signed in 1994, television companies such as RCA started to move their factories to Mexico in 1968 as a way to escape the high labor costs that resulted from labor organization in places like Memphis and Bloomington, Indiana. The recent Brooks Brothers article discussing the profit (or lack thereof) of manufacturing in Garland, and now this mention of manufacturing costs, makes me think someone should do a real history of the reasons classic American menswear shifted production overseas, and when (one not simply interested in trashing NAFTA, which while it certainly sped up a process, also hid the fact that the process was already ongoing.)

  27. Just a fantastic piece. Thank you!

  28. I’ve been super impressed with the new Hardwick blazers. American made. Exquisite attention to details. Approachable prices.

  29. Great interview. I appreciated how candid, unguarded and devoid of “marketing speak” it was.

  30. Roger Sack | May 3, 2018 at 2:02 pm | Reply

    “But I think it’s important remember that Press has made great strides in the past year re: a natural shoulder. The new Empire jackets feature a much better shoulder than the old Cohen jackets. ”

    “great strides”, indeed. Not being a menswear professional, I don’t understand why JP can’t
    just produce a shoulder like the one on a 30 plus year old JP suit that I still have.

  31. Roger: “But when manufacturers go out of business, as we’ve seen, it’s very difficult to replicate that exact cut.”

  32. Well, they can (produce a natural shoulder). The past decade has been a nightmare.

    Now that the Heyday generation are too old to buy clothing, J. Press will rely upon two, maybe three, groups:

    (1.) Street traffic in New York and D.C. Walk-ins. This is the accidental customer.
    (2.) The (generally speaking) “traditional” customer who might also buy something at Ben Silver, Paul Stuart or another fairly well-known store that tends toward traditional (even if updated) clothing. The guy who resists fads, and, even if he doesn’t give a damn about darts or pleats, wants blazers, tweeds and repp ties.
    (3.) The TNSIL Fogey. The citizens of Tradsville, whether 18 or 80. For whatever reason, they’re purists about Ivy style.

    A safe hunch is that they haven’t quite figured out how to shape the brand, guide the buying (cloth, manufacturers), or develop a marketing strategy. It’s all over the place. The fact that they stuck with Cohen and began offering slim-fitting, darted clothing (that doesn’t look good on anybody, including the skinny guys) reveals a remarkable lack of vision.

    But the new exec knows his stuff, so let’s hope he’ll get this old train back on the tracks.

  33. I’m no longer a J. Press customer. I’ve discovered two Southwick retailers who will make jackets and suits at very reasonable prices (less expensive than OTR) and a couple of shirtmakers who do the OCBD just right for just the right price. Just about everything that was once exclusive to J. Press is now available by other means (including Shaggy Dog sweaters*, tennis sweaters** and Atkinsons ties). What can we say? Retail is a tough game.

    *Shetland Woollen Co.
    **Smart Turnout

  34. A Trad Confused | May 3, 2018 at 5:35 pm | Reply

    Congratulations Robert, I look forward to seeing your impact at JP.

    Best,

    ATC

  35. Matt Olson | May 3, 2018 at 7:40 pm | Reply

    Great interview, thanks! Reassuring and exciting to hear about future plans for J. Press.

  36. Fantastic piece CC.

  37. The two Baby Boomers who would be most likely to make the trek to J. Press for shirts, ties and suits are, if the pictures speak truth, John Bolton and Howard Dean, who quite obviously occupy opposite ends of the political spectrum. Beyond the Yale degree, there’s probably something else at work. In terms of what they wear, almost countercultural. Maybe once the higher-ups at J. Press figure this out, they’ll have insights into their customer–the J. Press guy.

  38. whiskeydent | May 4, 2018 at 10:38 am | Reply

    There are men who don’t want to look like every other guy walking down the street. They want a sense of style that sets them apart without being garish or trendy. I count myself as one of them.

    I wonder if J. Press could reach out to these guys with a “dare to be different” appeal. Guys like this are comfortable with challenges; the meek need not apply.

  39. Charlottesville | May 4, 2018 at 3:44 pm | Reply

    whiskeydent — Spoken with all of the boldness of a true Texan! I agree, although I think that by wearing a linen tweed 3/2 sack sport coat and pink OCBD from Brooks with a PRL tie, khakis and tan bucks, I am sufficiently differentiated from the average guy on the street these days. For that matter, simply wearing socks at the office differentiates me from my young hipster friends in adjoining offices today, but that is a battle I don’t think I can win. At least one of them is wearing a (skinny) suit and tie. Hope you have a good weekend.

  40. whiskeydent | May 4, 2018 at 5:20 pm | Reply

    @Charlotteville
    No meekness in that outfit.

  41. If the J. Press customer is like a typical commenter on this site, it seems this gentleman understands what his customer cares about. Now for execution. Great read!

  42. Old School Tie | May 7, 2018 at 11:17 am | Reply

    Is shaving illegal in the US….?

  43. sharp dresser!

  44. Fantastic read.

  45. Parker Bradford | August 11, 2018 at 11:22 am | Reply

    Would you buy a blazer and flannels from a man who can’t afford a shave ?

  46. I suppose it would depend on how much I liked the blazer and flannels.

    Would you buy a blazer and flannels from a black man or gay man? Or is shaving the overriding consideration?

    Would you read a website edited by a bearded man?

  47. Great interview

  48. The last line of this article says it all “Everything’s changed”

Leave a comment

Your email address will not be published.


*