Caswell-Massey: The Legacy of a Heritage Brand

By Matthew Longcore Steeped in history, the seaside New England city of Newport, Rhode Island was founded in 1639 and is well-known for its vast array of Colonial and Gilded Age architecture. The White Horse Tavern, built in 1652, is one of the oldest taverns in the United States. The Redwood Library and Athenaeum, founded


Muffy Aldrich on the Preppiest New England Towns

By Matthew Longcore In her latest article, Muffy Aldrich from Salt Water New England lists New England’s Preppiest Towns, Villages, and Enclaves. I grew up in Westport, Connecticut and my grandparents lived on Prospect Road in the Green’s Farms section of town, a place on Muffy’s list. You may also know this area as the


The Collegiate Collection from Ebbetts Vintage

The Big Three Yale University 1923 Shawl Collar Sweater The Yale Football team has won 27 National Championships since they began competing in 1872.  Walter Camp, the “Father of American Football” was a Yale alumnus and coach.  Camp attended Hopkins School and graduated from Yale College in 1880. At Yale he was a member of


Ralph Lauren receives Presidential Medal of Freedom

Today, Ralph Lauren received the Presidential Medal of Freedom—the nation’s highest civilian honor. As the first fashion designer to receive the honor, Mr. Lauren received this award recognizing his contributions to American style, culture, and society for more than six decades. The Official Preppy Handbook Fan Club owes everything to Ralph Lauren. I collected Polo


The Shawl Collar Cardigan – An Ivy Classic

By Matthew Longcore The Great Gatsby is my favorite novel. While no film adaptation can ever live up to the writing quality of F. Scott Fitzgerald, the 1974 version starring Robert Redford and the 2013 version starring Leonardo DiCaprio each have great clothes. Ralph Lauren was the fashion consultant for the 1974 film and Brooks Brothers


Merry Christmas from Ivy Style

Merry Christmas from Ivy Style editor Matthew Longcore J. Press Brown/Olive Herringbone Sport Coat Polo Ralph Lauren Blue Oxford Cloth Button Down Shirt Brooks Brothers Navy-Red Silk Knit Striped Tie Archer Rust Corduroy Pants G.H. Bass Navy Pasadena Suede Bucks


The Duffle Coat – An Ivy Classic

By Matthew Longcore In 1989, when I was a high school junior, one of my favorite movies of all time made its debut on the silver screen. Dead Poets Society is set in 1959 at Welton Academy, a fictional boarding school, and was filmed at St. Andrew’s School, an Episcopal boarding school in Delaware. The


The Greatest Ivy Style Christmas Movie of All Time

By Dan Covell The end of every calendar year leads many to list-making: The top films of the year, the top books, the top eateries, etc. A group of friends and I, self-dubbed the “Fantastic Four,” met at Jimmy’s, a terrific cigar bar/restaurant in New Jersey and got a jump on this exercise to discuss


Christmas Music and The Power of Nostalgia

By Matthew Longcore Traditional, classic, timeless – these are the hallmarks of Ivy Style.  All of these are woven together by nostalgia. Nostalgia – that sentimental, wistful affection for the past – is heightened during the holiday season. Although we celebrate the holidays with our loved ones in the present moment, we are never exclusively


Ivy Style Holiday Gift Guide for Men

By Matthew Longcore Christmas is my favorite holiday for so many reasons, not the least of which is the music. As a lifelong Anglophile, I have always had an affinity for English Christmas carols. “Good King Wenceslas” is my all-time favorite, and I especially love the Celtic folk version from Loreena McKennitt on her 1995


Ivy Style Holiday Gift Guide for Women

By Sarah Bogart Cooney Sarah is the creator of the blog Fewer & Better and a contributing writer for Ivy Style. You can find Sarah on Substack. Christmas shopping for the traditional woman in your life (whether yourself or a loved one) is always fraught with difficulties. How do you know what is really worth


Main Line Style: The Perfect Loafer

Justin Jeffers is a self-proclaimed men’s style nerd and loafer guru. You may have seen his videos on his YouTube page The Fine Young Gentleman and you may follow him on Instagram at @fygblog. Justin grew up in the preppy Philadelphia suburb of Bryn Mawr. He attended The Shipley School and Villanova University before moving


Norman Hilton’s Ivy League Vision 1947–1970

By Nick Hilton A freshman at Princeton in the fall of 1937, Norman Hilton was introduced to the style of “St. Grottlesex” boys, graduates of elite New England prep schools, icons of Ivy League style. He admired, even coveted, the elite air of these men evident in the confident, patrician look of their clothing. He


For the Love of the Bow Tie

by Matthew Longcore Are you someone who wears a bow tie often? Occasionally? Absolutely never unless you’re in a tuxedo? Bow ties have been part of the repertoire of Ivy Style since its beginnings, but many of us prefer the four in hand necktie. Bow ties can seem fussier and more formal, perhaps because of


Ivy League Look in the New York Social Diary

In an article for New York Social Diary titled “If the Shoe Fits; Part I” (March 6, 2024), David Patrick Columbia describes the ‘Vassar-Yalie Prep school sensibility’ known as the Ivy League Look. According to Columbia: Brooks Brothers and J. Press were the two outfitters who drew the university/business/men and boys, and their mothers and


Stylish Interiors at Rooms With a View

By Matthew Longcore The charming coastal village of Southport, Connecticut has been described as “historic, with an aristocratic air.” Town & Country featured Southport in the July 1992 issue with the headline “Yankee Proud.” The article included several photos from legendary photographer Slim Aarons, including this photo of Albert Hadley, interior decorator to high society


Yale Daily News Features Ivy Style Editor

This article is reprinted from the Yale Daily News. PROFILE: Matthew Longcore GRD ’18 strives to democratize “Preppiness” Cody Skinner, Staff Reporter Whatever happened to the tennis sweater-clad, Sperry-loafer-wearing ‘Preppies’ whose style once dominated the halls of the prestigious private schools? Have madras sport coats and seersucker pants miraculously vanished from everyone’s closets? Not exactly.


English Tweed Suit by Abraham Moon & Sons

By Matthew Longcore Thank you to Ivy Style readers who have read the article about the Six of Clubs event this past weekend at Hill-Stead and asked about the clothes that I am wearing in the photo with David Dangremond. Here are the clothing items that I wore to the event: Ludlow Suit in Brown


Hill-Stead Museum Hosts an Elegant Evening

By Matthew Longcore This past weekend I had the great pleasure of attending a memorable evening of music and conversation at Hill-Stead Museum. For those unfamiliar, Hill-Stead is a National Historic Landmark property, an extraordinary Colonial Revival house set on a large estate in Farmington, Connecticut. The museum is well-known for its exceptional architecture, enchanting