Brooks Brothers Hosts A Nostalgic Evening

By Matthew Longcore

Most of us who appreciate Ivy Style have that sentimental brand that first introduced them to the timeless elegance of navy blazers, oxford cloth button down shirts, repp ties, and the like. For me, that brand is Brooks Brothers.

My earliest experience at Brooks Brothers was when I was a young boy in the early 1980s, visiting the New York store that once graced Madison Avenue. I believe that my first visit was during Christmastime, when New York City turns into a magical place. I recall being mesmerized by the sense of history and heritage at Brooks Brothers. It felt like much more than a store. More like a club, of sorts, and I wanted to become a member.

By the time I was in my late 20s, I had begun to think of a gentleman’s wardrobe as something worthy of  investment. Buy the classics, take good care of them, and they will last for many years. That became my motto then, and remains so today. Fortunately for me, around the same time that I developed this philosophy about clothing, Brooks Brothers opened a store in my hometown.

It is hard to believe that Brooks Brothers store in Westport, Connecticut has now been in the very same spot for more than a quarter century. During this period of time, Brooks Brothers has surely had its ups and downs, which has generated much discussion here on Ivy Style. We all know the old gripe – “it’s not the same as it used to be” – but respectfully, I think many of us who say that may not have set foot in a Brooks Brothers store for awhile now.

Under the brilliant guidance of creative director Michael Bastian, Brooks Brothers is on the rise. Much of the formula, as I have observed, is bringing back the iconic classics that made the brand famous. Materials like Harris Tweed from Scotland, OCBDs made in America, and sack suits featuring the signature 3/2 roll lapel.

Today, Brooks Brothers is thriving, and so too is the Westport store. In fact, the store is expanding. Having outgrown its longtime location, Brooks Brothers will soon move to a larger space:

After more than 25 years in Westport, Brooks Brothers will vacate its space in what used to be called Brooks Corner, at the corner of Main and Elm Streets. But they’re not closing. In fact, they’re moving a few yards away, to bigger digs. Brooks Brothers’ new location is 44 Main Street.

The new store is expected to open in early 2027. I will certainly be there for grand opening. In the meantime, I am enjoying visits to the store in the same location that I have loved for over 25 years.

On a recent visit to the Westport store, the manager Susan Civitano – a lovely person who is the very personification of excellence when it comes to creating a positive experience for customers – asked me if I might be interested in hosting an event at the store. The event came together quickly, with the help of a terrific caterer – A Dash of Salt from nearby Greenwich – and a guest list comprised of friends and Ivy Style readers, along with a few followers from social media.

We had a wonderful evening. Attendees included Rhys Moore from St Johns Fragrance Company,  Michele Cosentino from tennis clothing brand Top Banana, Jennifer Mathews from the Preservation Society of Newport County, and interior designers Scot Meacham Wood and Judy Fisher. Longtime Ivy Style readers were also in attendance, including William Candrick and Anthony Alexander.

For me, a highlight of the evening was wearing a new three-piece suit from Brooks Brothers, which was tailored for me at the Westport store. The Glen Plaid wool suit features a jacket with a 3/2 roll lapel, a 5-button fully lined vest with lapels, and trousers with side adjusters which I had cuffed.

I wore the three-piece suit with brown leather oxfords, a navy and white striped tie, and a vintage Brooks Brothers shirt from The Great Gatsby Collection. For Baz Luhrmann’s 2013 film adaptation, Brooks Brothers collaborated with costume designer Catherine Martin to manufacture over 500 period-accurate men’s ensembles, leading to a highly sought-after, limited-edition retail capsule.

I have to say, this new three-piece suit from Brooks Brothers just may be my favorite item in my wardrobe. The look is so retro, so vintage – and it represents everything I love about the history and heritage of menswear. In my article titled Three Cheers For The Three-Piece Suit from March of this year, I wrote:

According to trend watchers in the media, we are in the midst of a revival for clothing styles popular in the past. And of course, there is the old adage that everything good eventually comes back into fashion. If these sentiments are correct, let’s hope we can bring back the three-piece suit.

F. Scott Fitzgerald was a lifelong Brooks Brothers customer, and the brand is frequently mentioned in his novels. I must say, this suit is especially Fitzgeraldian. For me as one of Fitzgerald’s most loyal fans, that’s a good thing.

On  deeper level, the opportunity to wear something so reminiscent of  the past, was especially satisfying. I am firm believer that Ivy Style endures because of the power of nostalgia. Recently, my article on Ivy Style in the AI Age garnered some wonderful comments from readers.

S.E. wrote:

I’d argue the current impetus isn’t aspiration (ambition) so much as nostalgia, which is essentially sentimental in spirit. When I catch a glimpse, I do not assume the person is rich; the safer guess is that he/she is an “old soul.”

To which Charlottesville replied:

“Anemoia”: nostalgia for a time or place one never knew. The Polo ads of the 80s are an extreme, and extremely attractive, almost mythical example. I think a lot of us on this site have a fondness for a past which we may never have seen for ourselves, or perhaps glimpsed only in its waning days.

At the Brooks Brothers events, surrounded by old friends, I struck up a conversation with my new friend, William Candrick. He mentioned nostalgia and its importance to Ivy Style. We agreed that so many of us who love Ivy Style are inexplicably drawn to the past.

Today, in the middle of the 2020s, our world bears less and less resemblance to the 1920s. And yet, for me, that decade of a century ago has always felt familiar. I find the “old soul” concept that S.E. referenced, and the “Anemoia” described by Charlottesville, as completely relatable.

And I am reminded, as I consider this, of those famous final words in The Great Gatsby:

“So we beat on, boats against the current, borne back ceaselessly into the past.”