Usher In A New Era

Editor’s Note: Reprinted with permission from a FB Group post by Richard Clark

Usher will headline the halftime show at next Sunday’s Super Bowl LVIII. In 2005, the singer, songwriter, and dancer invested $9 million in the Cleveland Cavs, giving him a one percent stake in the team.

Not long after that, Usher flew a group of family and friends into town for a game. He also arranged for a private, after hours trip to the Brooks Brothers store near the arena and picked up the tab for whatever his guests selected.

Before it was permanently closed in 2020, the Brooks Brothers store in downtown Cleveland was one of the brand’s most beautiful locations. It occupied two floors in the historic Terminal Tower, Cleveland’s Grand Central Station. The Brooks Brothers store had been a bank when the Terminal Tower opened in 1929. It was a spectacular place to shop or just hang out, as I often did.

Ushers personal and professional taste in clothes goes far beyond Ivy Style. But he’s a big fan of preppy sportswear. And on that night in Cleveland, he bought stacks of v-neck sweaters in various colors and fabrics, as well as button-down and polo shirts.

Purists may scoff at this. But I take it as another sign of Ivy Style’s universal appeal and its pervasiveness. For me, it’s just another reminder of how cool Ivy really is.

26 Comments on "Usher In A New Era"

  1. I fancy myself a purist and would not scoff. I cannot see why anyone would scoff. I love it when anyone brings classic TNSIL or even a natural fabric riff on TNSIL into their wardrobe.

  2. John
    You are so right on . When I would visit my JPM team in Cleveland we had our office in that building. While traveling I would sometimes spill or forget something and I could run in and get a shirt or what ever and the service there was great. One time I spilled something on my suit coat at lunch,I took it to them and they had it cleaned and brought it up to the JPM office before I was to speak that night. That’s service.

  3. Weston Price | February 8, 2024 at 2:46 pm |

    Ivy is not “cool”. That’s its appeal to people of good taste.

  4. I don’t think “Ivy” is cool as much as “things that were originally Ivy are still popular.” The Articles of Style podcast touched on this, but to most people, the stuff we call “Ivy” are just clothes. Almost no one uses the term “Ivy” anyway. It’s “preppy” and even that has morphed well beyond its original meaning for a lot of people.

    People that dress in head to toe classic Ivy Style may be well dressed, but your average person would probably never say “that guy looks cool.”

    • John Burton | February 8, 2024 at 6:59 pm |

      Not sure I agree. I think at this stage of the game everyone who is well dressed looks cool. And people will say so.

      • No offense but I teach high school and the teachers who dress like we do are seen as kind of quaint weirdos from the past. Not saying it’s uncool but it’s definitely not “cool” I promise you.

  5. I agree that Ivy is cool. Especially in the modern-day context. It is indeed a raised fist of defiance, raging against the “athleisure” and “fashion runway” machines. Ivy has quarreled with a variety of looks and styles since it was codified (okay, marshaled) by Brooks way back when. While it’s true I’ll insist on more than a few well-defined parameters, I’ll allow that there’s plenty of room for interpretation. And, of course, there are several interpretations and expositions of the style, and, as such, a congregation of emissaries and ambassadors.

    Interesting — the coolest people I’ve known have favored his/her own unique rendering of this style. As I reflect, a lot of the “not at all cool” people I’ve known have favored other looks.

  6. “Everyone who is well dressed looks cool.” Truth. It’s the relaxed, insouciant, fashion-defying ease that sets Ivy apart — from the rest of the spiffed-up crowd. The appeal, and what makes it so unique, is the effortless, piece-of-cake merging of formality and laxity. The Pitti Uomo and Paul Stuart devotees look great (admittedly), but it’s, well, “a lot — a bit much.” Whereas Ivy lolls and loafs — sportily and indifferently. Nonchalantly.

  7. Sure. I agree. And similarly, there are those “posers”, those who are “not at all cool”, who think that dawning the Ivy look will make them cool. It doesn’t work that way. For while a man can put on an orange and blue football uniform with the number 7 on the chest, that doesn’t make him John Elway. Ivy style, within “well-defined parameters” is the cool style. But cool is an essence which cannot be purchased. One must take a long, hard look in the mirror, make an honest self-assessment, and ask oneself, “is you is, or is you ain’t?”

    And, to be fair, I know a lot of very cool people who’ve never been exposed to the style, as it is nowhere near as pervasive as it was in the heyday.

  8. John I agree with you “that anyone who is well dressed is cool”. In this era we don’t find too many people WELL DRESSED” Ivy people cared how they dressed and they way they presented themselves. Ivy style is cool and a wonder clean and well dressed look.

  9. MacMcConnell | February 9, 2024 at 1:44 pm |

    “It is indeed a raised fist of defiance, raging against the “athleisure” and “fashion runway” machines. ”

    So Ivy is the “New punk”. 😉

    “Everyone who is well dressed looks cool.”

    Yes, no and sometimes.

  10. Ivy Style Reader | February 10, 2024 at 4:51 pm |

    Can someone do a detailed description of Tucker’s clothing during his Moscow trip, both during the interview itself as well as when he was outside, in the airport, etc.

  11. What if you won a shopping spree at Brooks Brothers, or J. Press, The Andover Shop, O’Connell’s, etc. or somewhere more like J Crew, Banana Republic, Jos. A. Bank, etc. or TJ Maxx, Marshalls, Nordstrom Rack, Saks Off 5th, Century 21, etc. … Let’s say you won a $10 – $100 spree, around $250, $500, $1,000 or more than that. What if there were no limits on place or price? What would you get?

  12. But by definition, if one is concerned with one’s coolness, one isn’t cool.

    Be neat and clean, thrifty but not stingy, friendly but discerning, reasonably well-read, patriotic, reliable, etc, and don’t worry about the malarkey.

  13. Bop
    You mean an Eagle Scout?

  14. Felix, I could use a new pair or two of Pantherella Laburnums, mid-calf in navy. A tie or two might be fun, but only if it makes me cool. I find the fantasy spree a curious comment, but I guess Usher went on one.

    Bop, you got that right.

  15. Fantastic stuff. Some of the best ambassadors of the “trad” look never went anywhere near a prep school. Miles Davis, Chet Baker, and now we always see Wynton Marsalis and his Lincoln Center Jazz Orchestra always in blazers and repp ties. Reading the oral history of Charlie Davidson and the Andover Shop or Ricahrd Press’s stories about Frank Sinatra, and there have always been top notch entertainers who looked to use Ivy and “make it their own” just as they did with music.

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