Ivy Style interview with Robert Squillaro, executive at J. Press

Ivy Style had our first interview with Robert Squillaro, Senior Vice President and Chief Merchandising Officer at J. Press, back in 2018. We recently spoke with Robert again to ask him some questions about menswear today and the position of J. Press as a leading purveyor the Ivy League Look. — Matthew Longcore

IS: Hi everyone. Today Ivy Style is with J. Press executive Robert Squillaro. We have 10 questions for Robert and I’m going start with a very basic question: Robert, how did you get started in menswear?

RS: I’ve always had an interest in men’s clothing style and style in general. When I first started college I was taking general business classes and I wanted to focus on something more specific, so I took a few retail classes. After my sophomore year my mother gave a brochure for FIT and after meeting with the dean of the business school I decided to give it a try.

Ivy Style exhibit at the Fashion Institute of Technology Museum (2012 to 2013)

I was really interested in the curriculum, especially as a New York resident living in the fashion capital. The professors there allowed me to cater my curriculum to menswear as opposed to womenswear, which was the primary focus at the school. I took an interest in many of the American heritage brands like Brooks Brothers, J. Press, and Ralph Lauren. When I finished at FIT, I got a job in men’s retail. I started out as holiday sales help on the main floor of the Brooks Brothers Store on Madison Avenue and did that for a few months and then moved into their training program. From there I worked my way up through various executive positions and it’s been a lot of fun ever since.

IS: That’s great to hear – so Brooks Brothers was your start, when did you join J. Press?

RS: I joined J. Press in January of 2018 after having spent the seven years prior to that in my second stint at Brooks Brothers.

IS: J. Press, of course, is a leader when it comes to Ivy style – what is the competitive advantage?

RS: I think two things: authenticity and the fact that J. Press has really never strayed from what they’ve done since their beginning in in 1902. Also, the fact that we still make and source just about everything in the countries and type of factories that we always have used since our beginning is important.

As an American heritage brand, we make everything we can in the United States, and when we can’t, we make in Canada and the United Kingdom. While most of our competitors have shifted their sourcing to other low labor cost countries, we’ve stayed true to American manufacturing and British influence.

IS: J. Press remains rooted in the United States and the United Kingdom – that makes perfect sense for an ivy brand. Which clothing items from J. Press would you say are considered the most iconic?

RS: If I had to pick the top item, it would probably be our Shaggy Dog sweater.

IS: I would certainly agree with that.

RS: During the years I worked for other brands, when I thought of J. Press I thought of the Shaggy Dog sweater first, followed by the flap pocket Oxford cloth button down shirt.

IS: Haha, you’re reading my mind. Those would be my answers to my own question.

RS: Another iconic item would be our tweed sport coats that have a vertical stripe decoration in them, especially our Donegal Mist cloth. These three items are probably the most unique to J. Press. Of course we carry all of the classic items as well, American made chinos, sack suits, non-flap pocket oxfords, Scottish cashmere cable knit sweaters, madras, seersucker – all the great classics. But I would say those three items are somewhat unique to J. Press.

IS: Here is an important question, especially coming from me as the founder of the Preppy Handbook Fan Club and now the editor of Ivy Style: are “Ivy style” and “Preppy style” the same? And if not, how would you say that they differ?

RS: I don’t think they’re the same, but I also think you can get overly caught up in the exact specifics of what the different definitions are. Ivy style came first, and preppy followed much later. I remember Ryan O’Neal being called “preppy” in the movie Love Story in 1970, but the term “preppy” really wasn’t a big thing until probably the late 70s/early 80s.

Ali MacGraw and Ryan O’Neal from the movie Love Story

Ivy style really gets its roots in what we would call “trad” clothing. Many of these items were worn together in a nonchalant way by college students that created what we now define as ivy style.

IS: In her blog Saltwater New England, Muffy Aldrich writes that there is “the thing before preppy.” Ivy style is part of that thing before preppy. It’s an earlier thing.

RS: That’s correct. Now you can take a lot of the anchor pieces and see that they sit in all three styles – Ivy, Traditional, and Preppy. For example, penny loafers, OCBDs, khakis, polo shirts, and navy blazers are all three.

IS: A Venn diagram of overlapping things – sure, that makes sense.

RS: When I think back to that late 70s and early 80s prep, there was a lot of color. You would see lime green, hot pink, yellow and orange, most notably in polo shirts and chino pants. You started to see those colors in traditional fabrics too. Madras was done in pastels as opposed to many of the muted darker colors that had been done prior to that.

IS: Yes absolutely, that’s very much what we associate with 80s prep. J. Press, of course, is very traditional in many respects but it also does evolve with changing times. How so?

RS: Well, you know, one of the ways you have to change is with methods of manufacturing as some things are just not made the way they once were. Some fabrics aren’t made any longer and many have gotten lighter in weight, which makes them more wearable than fabrics in the past.

As far as the actual style is concerned, one glaring change would have to be that suits and ties are not being worn to work every day by most men as they once were. We’ve had to shift to sport coats and sweaters and sales of both have grown tremendously. We do a great job with our sport coats. To me, it’s a much cleaner and sharper look to throw on a jacket over your open shirt, rather than wearing a fleece vest or nothing over the shirt at all.

IS: These days is J. Press selling mostly in its brick-and-mortar stores or online?

RS: Obviously during COVID for most retailers everything was being done online. During the aftermath, our business started to shift back to the stores. Nevertheless, the J. Press website is still is our biggest store, although our retail stores have recovered nicely and are exceeding pre-pandemic sales metrics.

IS: Would J. Press ever consider offering womenswear?

RS: That is something that I would love us to get into. We have talked about it, but right now we have other priorities. Believe it or not, some of our vintage catalogs from the 60s did feature womenswear.

IS: Interesting! I had no idea.

RS You know, we have plenty of women today buying our Shaggy Dog sweaters but a true women’s version would probably be better fitting if we shortened the sleeves and body a little bit for the female torso. Our entry level brand that we currently call Pennant Label would probably be where we were would consider offering womenswear first.

IS: I can tell you of an occasion where a woman shopped for herself at J. Press. My father went to Brown University and wanted a Brown muffler for a football game. We went to J. Press to pick it up and my stepmother saw a red and white muffler in the school colors from Miami University in Ohio. She bought it for herself and they both wore J. Press mufflers at the game. It was fun. So yes, I think the idea that women might pick up something that was made initially for men has always been an option. Speaking of items of clothing, what is the one item that every loyal J. Press customer must own?

Brown University Schoolboy Muffler

RS: I’m going to go back to the Shaggy Dog sweater – you really need them if you’re going to be a true J. Press fan. We have both classic and trim fits. The trim fit is a lighter weight lambswool Shetland. It’s a little bit easier to wear in an indoor environment. The original classic is a pure Shetland yarns. If you look closely at the compound colors, you have many different colors making up the overall sweaters. They are spectacular.

IS: I’ve had the traditional fit several times over the years but it sounds like heading into the fall, especially with the office that I work in which is an old building at Yale, I would probably be happy with the trim fit that you described so I think I’m going to give that a try myself. I saw a really nice one in in a light gray, so I have my eye on that one.

Shaggy Dog Sweater in Mid Grey

It’s the end of the summer, unfortunately, for those of us who love summer. But it’s also exciting as we’re heading into the fall season and that’s a great season for clothing. Is there anything on the horizon for the fall collection the upcoming season that Ivy style readers and J. Press customers should be aware of you?

RS:  We’ll have our usual 20 plus colors of Shaggy Dog sweaters and this season we’re bringing back the cable knit Shaggy Dog crewneck as well.

IS: Oh nice! I love cable knit sweaters.

RS: We’ll also have our usual 16 colors of English corduroy trousers and both our Donegal Mist and Harris Tweed sport coats are now available in a very light unconstructed model, so it takes some of the weight out of the coat and makes it a lot more wearable. The fabrics are sturdy enough that it doesn’t need all the interior components to give the jacket body and you get a perfect natural shoulder.

We’ve added colors and patterns to our collection of duffle coats this year. If you’re looking for something to put on when the weather gets a little cooler, we’re offering a range of boiled wool overshirts that offer a clean look.

We have cotton moleskin sport coats that look great with our range of sport shirts. We’ve also added in a lightweight cashmere crewneck sweater as an alternative to our chunky heavyweight and our cable knit cashmeres – all knitted in Scotland.

I think we’ve got a great lineup of products in our Pennant Label. We’ve added some more tailored components such as tweed jackets and pinwale corduroy sport coats with matching bottoms along with a full range of Oxford cloth shirts including a spread collar option. There’s a lot to choose from. In addition, we offer made to measure tailored clothing and shirting program.

IS: I look forward to perusing the J. Press catalog and to picking out some nice items from the fall collection.

Robert, thank you very much for taking the time today. It’s been a pleasure speaking with you.

RS: Thank you, Matthew. You know I could sit and talk to you for hours about all elements of clothing and fashion – Ivy style and preppy style – as well as competing brands and fabrics. Please reach out again if you or your readers have any further questions.

32 Comments on "Ivy Style interview with Robert Squillaro, executive at J. Press"

  1. Mr. Squillaro shows an excellent sense of ivy style, but I have two nits to pick. I love his touting the heritage brand and all. Press proudly proclaims made in USA or made in Canada when applicable, but an increasingly high proportion of goods simply say imported. Is that code for offshoring to countries not usually associated with the ivy ethos? Also, a return engagement with Brooks, decades after it had completed a major shift away from its own heritage, surprised me. Times change. Styles change. Press has changed far less than most but not all.

    • Matthew Longcore | September 4, 2024 at 1:39 pm |

      Tim, just a point of clarification – Heritage products from J. Press are made in the USA, UK, and Canada. Pennant Label products from J. Press are sourced from a variety of countries in order to offer lower prices as this is their entry level priced collection.

  2. @ Tim, are you opposed to JPress importing tweed, corduroys and knitwear etc from Britain? And genuine Madras shirts from India?

  3. Nice interview. I hope you get the chance to do a similar interview with Brooks Brothers. As Brooks has recently dived into the vault for a “Heritage Collection,” it would be interesting to get their perspective on Ivy Style and how they view their role in moving the style forward.

    • Matthew Longcore | September 4, 2024 at 1:44 pm |

      Joe, thank you for the positive feedback. It was a pleasure to interview Robert Squillaro from J. Press. I am planning to interview Michael Bastian, creative director at Brooks Brothers. We will discuss Michael’s perspective on Ivy style and the Brooks Brothers heritage collection.

  4. Great interview. I enjoyed perusing the Pennant Label look-book when it was released online the other day. While I’m not so young anymore, I keep a trim enough figure that PL fits me just right. I already eyeballed what I hope to order once the official fall brochure (and its coupons, knock on wood) are released closer to autumn. It’s wonderful that I can always count on the seeming oxymoron of catching something new from Press that I want, all while they generally maintain their roots. Bravo.

    • Matthew Longcore | September 4, 2024 at 1:53 pm |

      Eric, I have become a Pennant Label fan based on style and price. I especially like the Yale bulldog items which are much nicer than anything one can find at the university bookstore. They remind me of a bit of The Yale Co-op.

  5. Hear, hear. Donegal Mist and Harris Tweed!

  6. Poison Ivy Leaguer | September 2, 2024 at 1:52 pm |

    A trivial factoid and an opinion:
    According to the credits, Ryan O’Neal wore Botany 500 in Love Story.
    Regarding the Ivy vs preppy semantic teapot tempest, I believe that Ivy is preppy. The look was not popularized by scholarship students from Arkansas. It was popularized by the rich St. Grottlesex boys.

  7. the passenger | September 2, 2024 at 1:55 pm |

    Here’s a question for Mr. Squillaro: on most Oxford shirts, the top of the pocket has fabric folded over and sewn with a V shape. On the J. Press oxfords that do not have a flap pocket, the fabric is folded over and sewn straight. (The current Brooks shirts I have seen also have this.) Why not the V? It’s a small thing, but the V seam looks a lot better to me.

    • Interesting. I have five BB MTM shirts, two OCBD, three Broadcloth, selected for their beautiful, non-stocked stripes. All five have the straight pocket seam. 🧐 Garland factory? There for awhile, BB couldn’t be bothered to provide a pocket.

    • Matthew Longcore | September 7, 2024 at 12:57 pm |

      I shared your question with Robert Squillaro. Here is his response:

      Both J. Press and Brooks Brothers have the same pocket hem stitching because most of our standard pocket ocbds were made in the same factory and that factory was only able to offer the straight hem stitching. The two different hem stitching is a matter of style preference and either is correct. Our flap on our flap pocket shirts have a V shape so we were fine with using the straight hem stitch on our standard pockets for a different look.

  8. J.Press and Chipp were nextdoor neighbors on 44th Street- across the street from Brooks.
    Press had the “Shaggy Dog” shetland sweaters and Chipp had an equal number of colors of shetlands that were not “shaggy.”
    Some preferred the J.Press sweater and some preferred the Chipp sweater- both were fine quality.
    As Richard Press will attest-he joined his father and uncle at J.Press a year or two before I joined my father at Chipp- the relationship we had with our suppliers was very different in the “good ole days.”
    If you had a question to ask a supplier you picked up the phone and in a minute or two you were talking to the owner of the company.
    It was not unusual to find the owner of different companies in my father’s office.

    Our sweaters were supplied by E S Deans and Company.
    The Deans NY office was next door to our shop.
    A day or two a week I would find Effingham Deans- a born Scot with a thick Scottish accent- having lunch with my dad in my dad’s office.
    His sweaters were very good quality.
    The Deans sweaters cost us what Press was paying for their sweaters.

    Each sweater had a label that said in large letters – DEANS OF SCOTLAND. At the bottom of the sweater was a small tag that said in very small letters- made in Hong Kong.

    Not everything that is “imported” is poor quality.

    • Matthew Longcore | September 4, 2024 at 2:01 pm |

      Paul, great history about J. Press and Chipp, thank you for sharing. Excellent point about the relationship between quality and something being imported. Harris Tweed comes from the remote islands of the Outer Hebrides and authentic Madras comes from Chennai in south India.

  9. Poison Ivy Leaguer | September 3, 2024 at 11:54 am |

    Mr. Winston’s comment reminds me of an old favorite, Shetland sweaters by J & D Mc George, Ltd. of Dumfries. John Wanamaker sold them in Philadelphia, and Larrimor’s sold them in Pittsburgh. Does anyone else remember that brand?

    • Matthew Longcore | September 4, 2024 at 2:06 pm |

      I remember Wanamaker fondly. My father – a graduate of Brown and Cornell – lived for many years in Abington Township, Montgomery County, Pennsylvania. We shopped at Wanamaker frequently.

  10. Charlottesville | September 3, 2024 at 12:07 pm |

    Thank you Matthew and Mr. Squillaro for the excellent interview. I am thankful that J. Press continues to provide authentic Ivy clothing as it has for well over a century, and is bringing in younger customers with the Pennant Label. I am also glad to hear that the brick and mortar stores are still prospering.

    And thank you. Mr. Winston for reminding me about Deans of Scotland. Their sweaters were a mainstay in Charlottesville in the 70s and 80s. I wish I still had the Deans cable crewnecks that I had back then.

    • Matthew Longcore | September 4, 2024 at 2:07 pm |

      The brick and mortar J. Press store is thriving here in New Haven, Connecticut. The excellent customer service beats shopping online any day.

    • My parents would always bring back Deans sweaters from their annual Bermuda trips back in the 1970s. I had a nice little collection as a teenager, often worn with faded jeans and tennis sneakers.

  11. Stoics Society | September 3, 2024 at 4:04 pm |

    I had the pleasure of meeting Mr. Squillaro a while back at a J. Press event. As a female fan of the brand, I also questioned him about a women’s line. He directed me to the newer trim-fit Shaggy Dogs. Game changer!

    • Matthew Longcore | September 4, 2024 at 2:09 pm |

      Tammy, the trim fit Shaggy Dog sweaters are a great choice for women! As I mentioned in the interview, the schoolboy scarves also have unisex appeal.

  12. I agree that “imported” does not necessarily signal “poor quality” but let’s not confuse the issue here. There is a marked difference between “imported from the country that originally made these goods” (such as wool sweaters from Ireland or Scotland, for instance) and “imported because the labor costs in Vietnam are low.” There is some nuance here for certain and we should not pretend that these are the same things.

  13. Charlottesville | September 4, 2024 at 10:26 am |

    By the way, the new J. Press look book is out online and it really looks great. In my opinion, FWIW, it is perhaps the best in a couple of years. Gorgeous tweeds, sweaters, cords and some beautiful suits as well, and all well presented in the photos. Congratulations to Mr. Squillaro and the people who put it all together.

    • Matthew Longcore | September 4, 2024 at 2:11 pm |

      I agree about the fall collection. So many items that I need in my wardrobe. Looks like I am going to need a bigger closet.

  14. The past few years have witnessed yet another revival of all (okay, many) things antique, vintage, and yesteryear, including but not limited to clothing. A lot of my friends are “into vintage,” and the social justice-inspired “slow fashion” and “fair trade/manufacturing” movements are de rigueur among friends, neighbors, and colleagues. We’d all stand guilty-as-charged of being so-called “overeducated eastern elites.”

    It might be argued that this (present) moment is the best (yet) for clothing that salutes pre-WWI Brooks. Since it has been acknowledged, affirmed, and admitted that J. Press and their campus shop imitators were basically, for all practical purposes, imitating old Brooks Brothers, I wonder how “far off the reservation” some of the more pedestrian campus shops took the look. I was never a fan of Weejuns or overly the mod-ish trim/skinny tailoring; I was always more drawn to the Victorian/Edwardian Anglophilia of early 20th century Brooks. There’s reason to believe that a youthful Ralph Lauren was inspired by similar instincts.

    Options now abound. Shirts? Mercer & Sons. Knitwear? Harley of Scotland (woven and made there). Outerwear? Cordings. Shoes? Crockett & Jones. Easy and immediate access to a diversity of retailers. Ben Silver and The Andover Shop are commended for persevering in their salutes of pre-WWI Brooks — appreciative of the iconoclastic, slightly eccentric, decidedly Anglican traditionalism at the heart of it all. If Ivy was before Preppy, Edwardian Anglophilia (think Brooks circa 1913, sans waist coats) was before that:

    https://www.whiffalumni.com/whiffs/group.php?groupyear=1913

  15. I am not opposed to woolens from the UK, Madras from India, or shoes from Italy. I am not even opposed to suits from China, shirts from Viet Nam, or boots from Mexico. I am merely pointing out that certain non-Pennant items offered by Press are simply labeled “Imported.” Many countries, the USA included, can put out substandard goods as well as truly fine goods, and many countries, the PRC and others included, are able to offer some goods that are exceptionally well crafted. By choice, I buy chiefly made in the USA, the UK, or Canada products, but it bothers me how many retailers and manufacturers go to great lengths to obscure their true provenance. If you offer incredibly high quality goods made in China or India, just say so.

  16. USC Class of 1976 | September 4, 2024 at 5:33 pm |

    Just saw the J. Press email today previewing their Fall ’24 offerings. Looks like a lot of great stuff. My problem is that for the past half dozen years or so, almost no odd jackets are available in “larger” (I am a 48 L/XL) sizes. Having been a Press customer of about 40 years, I find this disappointing. I have in the recent past purchased jackets from O’Connell’s and the Andover Shop. Given my druthers, Press would still be my first choice. When the late John Jackson (RIP) was still at the 44th Street location, seeing him was always a highlight of my frequent trips from LA to NYC. The staff at the Yale Club location remains great. Earlier this year, I shared my “J. Press Club Card” (circa mid-1980s) with a young associate. Seems he had never seen one before…Here’s to some “plus sizing” in the coming year(s).

    • Trojan,
      I’m not L/XL, but I, too, am impossible to fit OTR/RTW, making MTM or Bespoke the only options. Can you say “EXPENSIVE”? Quality materials are too expensive for retailers to keep less common, especially large sizes, in inventory. I understand that. Manufacturers require retailers to take on a required number of assembly line products. I buy shirts online because I can. Jackets or suits…No way.

  17. Another great article. Have a few older J.Press pieces, but as of late have really been enjoying Pennant. Most all my OCBDs, short sleeve (both ocbd and madras) popovers, rugbys, sweatshirts and even a couple of polos are Pennant label. Ashamed to say I ruined the one Shaggy Dog I had… but, that is certainly next on the list!

  18. The fall lookbook looks great–so nice to see J Press returning to it’s core–and not chasing trends. Love the presentation and photography. Well done!

  19. Gave a cursory look to the online preview of the Fall ’24 look-book the other day, and as usual lots of great looking items to covet. Sadly, there is really nothing else I “need” at this point. Still looking forward to the arrival of the physical catalog in the mail however. I’ll quietly leave it in my son’s room a day or two later. The power of suggestion and all that.

    Kind Regards,

    H-U

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