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 …

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 …

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 …

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 …

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 …

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 …

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 …

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 …

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. …

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 …

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 …

By Matthew Longcore “Shopping from the Lilly catalog is a Preppy’s idea of walking on the wild side. The clothes here – men’s and women’s resort wear – are totally out of control in prints famous for their distinctively intense shades of lime green, shocking pink, and electric yellow. Count on at least four women …

By Dan Covell Earlier this year, Ivy Style posted my essay on the power of style on dress and contemporary music. That piece noted other previous contributors to this site who marked the many connections between Ivy Style and music, starting with jazz titans Chet Baker and Miles Davis, through Richard Press’s dalliances outfitting Frank Sinatra. …

The 40th Annual Harriman Cup Polo Match between alumni teams from Yale University and the University of Virginia featured lots of classic Ivy style, including madras sport coats and rowing blazers. Here are a few photos of Ivy Style editor Matthew Longcore and other revelers, including Jack Carlson, the founder of Rowing Blazers. Matthew is wearing …

There is nothing quite like a personalized gift.  A custom needlepoint belt from Fish Creek Brands is the ultimate gift for your favorite person. October 1st is the deadline to order a custom belt in time for Christmas. Needlepoint belts from Fish Creek Brands are 100% hand-stitched with a cowhide leather backing and a solid …

Ivy-Style.com and the Preppy Handbook Fan Club have teamed up with our friends at St Johns Fragrance, Jay Butler Shoes, and Classic Fella for an Ivy Style Giveaway! The winner will receive a fantastic collection of items including: ST JOHNS FRAGRANCE Vetiver Set – 4 ounce spray, soap, mini travel size, and deodorant The Philosophy …

by Matthew Longcore The J. Crew catalog is a fond memory for those of us who came of age in the late 1980s and went to college in the early 1990s. At my undergraduate alma mater, Trinity College in Connecticut, stacks of J. Crew catalogs were delivered regularly to the mailbox area in Mather Hall. …

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 …

by Matthew Longcore Founded in 1846, Town & Country is the oldest continually published general interest magazine in the United States. The magazine chronicles American high society and regularly features articles on style and fashion. A newer segment called The Weekly Covet features editor-approved lists for fashion, travel, and other lifestyle topics. This week the …