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 …

In the heyday of the Ivy League look – that golden era between This Side of Paradise (1920) and The Official Preppy Handbook (1980) – a group of legendary menswear shops clustered in midtown Manhattan around Madison Avenue and 44th Street. The big four – Brooks Brothers, J. Press, Paul Stuart, and Chipp – catered …

The Harriman Cup is an annual polo match between alumni from Yale University and the University of Virginia. This year marks the 40th Annual Harriman Cup Polo Match. The event will take place on Saturday, September 14 at Bethpage Polo at the Park in Bethpage, New York. Ivy Style and the Preppy Handbook Fan Club will …

“American Ivy” is a podcast from Avery Trufelman which discusses the origin of preppy style, its evolutions and comebacks, and the cultural expression that underlies clothing. In is a series of 7 episodes from Articles of Interest, Trufelman focuses on the Ivy League look, a style which includes chinos, polos, sweater vests, and loafers. The …