The Ivy League Style Guide: The Art of Timeless Fashion

AFFILIATE DISCLOSURE

The Fashionisto

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Updated June 25, 2024

Ivy League style menPin
Explore the timeless appeal of Ivy League style.

The Ivy League style, marked by timeless staples like Oxford shirts, tweed blazers, crewneck sweaters, and penny loafers, emerged in the early 20th century. It drew inspiration from prestigious private schools and universities like Harvard and Yale, where British tailoring merged with American collegiate sportswear.

This blend of influences gave rise to a distinctive aesthetic that embodied academic excellence and effortless sophistication. By the mid-20th century, the Ivy League look had become integral to American culture.

Ivy League Style Essentials

Cable knit v-neck sweater Brooks Brothers Ivy League style menPin
Channel the Ivy League aesthetic with a cable knit v-neck sweater and polo. Photo: Brooks Brothers

The Ivy League style, epitomized by institutions such as Princeton and Columbia, exudes intellectualism, elegance, and refinement while remaining humble and approachable.

While it shares similarities with preppy style, the Ivy League aesthetic tends to be more understated and refined, focusing on timeless simplicity rather than bold colors and patterns.

Oxford Shirts

Oxford shirt Banana Republic Ivy League style menPin
Evolve your wardrobe with the timeless charm of the classic Oxford shirt. Photo: Banana Republic

Steeped in history, the Oxford shirt has been a wardrobe staple for generations, dating back to the early 20th century. Crafted from Scotland’s famous Oxford cloth, prized for its quality since the 19th century, these shirts boast a rich heritage.

They are revered for their exceptional durability and enduring style. Whether elevated with a tweed blazer or dressed with casual khakis, the Oxford shirt’s versatility has solidified its status as a must-have for anyone embracing the Ivy League aesthetic.

Polo Shirts

Polo shirt J.Crew Ivy League style menPin
The polo shirt is an excellent smart-casual style worn casually or dressed up. Photo: J.Crew

René Lacoste originally designed the polo shirt for tennis players in the 1920s. By the mid-20th century, Ivy League students had adopted the polo shirt to symbolize relaxed yet refined fashion.

The polo paired perfectly with everything from casual chinos to formal trousers. Today, the polo shirt exudes effortless sophistication and classic style, often seen in vibrant colors and paired with penny loafers.

Ivy League Sweatshirts

Harvard sweatshirt Ivy League style menPin
Ivy League sweatshirts exude timeless charm when worn solo or layered under jackets. Photo: The Harvard Shop

The Ivy League sweatshirt has become a cultural icon, blending athletic wear with timeless style. Emblazoned with iconic logos or crests, they proudly endorse esteemed institutions like Columbia and Dartmouth.

Their enduring appeal has led to mainstream collaborations between elite schools and brands like H&M and PacSun, making Ivy style accessible through various clothing, from t-shirts to sweatshirts.

Cable Knit Sweaters

Cable knit sweater Mango Ivy League style menPin
Cable knit sweaters marry equal parts style and coziness. Photo: Mango

Initially worn by fishermen for warmth, cable knit sweaters gained popularity for their intricate patterns and cozy feel. Their textured, dimensional design and soft, plush yarns create a sense of rugged sophistication.

They are often layered over Oxford shirts or under blazers, add classic style to any outfit, and remain a staple in many Ivy League wardrobes.

Blazers & Sports Coats

Navy blazer Tommy Hilfiger Ivy League style menPin
Make a sartorial appearance with a rich navy blazer. Photo: Macy’s

Navy Blazers: Rooted in 19th-century British Royal Navy tradition, the navy blazer was later embraced by elite American colleges, becoming an Ivy League wardrobe staple.

Crafted from versatile fabrics, such as wool, it effortlessly transitions from formal events to business meetings and casual gatherings, earning its status as a timeless wardrobe essential.

Flannel blazer Suitsupply Ivy League style menPin
Find great versatility in the flannel blazer. Photo: Suitsupply

Flannel Sports Coats: Flannel blazers, made from soft, brushed wool, provide warmth for cooler months. Typically in solid colors or subtle patterns, they embody understated sophistication, aligning with the Ivy League’s emphasis on classic, refined clothing.

Pair them with flannel trousers, chinos, jeans, or corduroys, and dress up with a tie or down with a crewneck sweater.

Moss tweed blazer Ivy League style menPin
Bring a rugged but refined sensibility to your wardrobe with the tweed blazer. Photo: Moss

Tweed Blazers: Tweed blazers, rooted in Scotland’s rugged countryside, are crafted from durable, water-resistant wool. They’re prized by the Ivy League elite for their practicality and timeless elegance.

With textured, earthy tones, they’re versatile for formal and casual settings, often paired with wool trousers or khakis and layered over button-downs and knitwear, epitomizing scholarly style.

Chinos & Khakis

Chinos Charles Tyrwhitt Ivy League style menPin
Chinos seamlessly bridge the gap between smart and casual. Photo: Charles Tyrwhitt

Chinos and khakis offer a perfect balance between casual and formal. Originating from military uniforms, these cotton trousers became popular on college campuses for their comfort and versatility.

Typically worn in beige, navy, and olive shades, they pair well with everything from blazers to polo shirts.

Varsity Jackets

Varsity jacket Brooks Brothers Ivy League style menPin
Add sportiness to your casual attire with the classic varsity jacket. Photo: Brooks Brothers

Also known as letterman jackets, varsity jackets are a staple of American college culture. Typically featuring a wool body and leather sleeves, they often boast patches or letters signifying school spirit and achievement.

Today, they’ve evolved into a fashion statement, transcending their athletic roots to add a sporty, youthful touch to any wardrobe.

Peacoats & Trench Coats

Peacoat Quince Ivy League style menPin
The contemporary peacoat pays a nod to naval style. Photo: Quince

Outerwear forms the backbone of Ivy League style, born from the region’s unpredictable New England weather. The Peacoat, steeped in naval tradition, brings warmth and elegance to colder weather, typically in classic navy or black hues.

Meanwhile, with its military roots and timeless design, the trench coat offers a sophisticated solution for rainy days.

Neckties & Bowties

Brooks Brothers repp tie Ivy League style menPin
The stylish repp tie reigns supreme as a classic Ivy League accessory. Photo: Brooks Brothers

Ivy League neckties and bowties are renowned for their signature patterns, including classic stripes and Glen plaid, which have become hallmarks of esteemed schools and clubs.

These timeless designs infuse a sense of heritage and tradition into one’s attire, with striped ties often featuring school colors, repp ties characterized by diagonal stripes, and Glen plaid ties and bowties serving as distinctive accents.

Footwear

Ivy League campuses have a long history with three timeless shoe styles, each embodying a unique aspect of the polished, collegiate aesthetic:

Penny Loafers G.H. Bass & Co. Ivy League style menPin
G.H. Bass & Co. is one of the industry leaders when it comes to the classic penny loafer. Photo: G.H. Bass & Co.

Penny Loafers: In the 1930s, G.H. Bass & Co. introduced the classic “Weejuns” model, featuring a stylish strap with a distinctive slot. This design quirk sparked a clever tradition.

Students would store pennies in the slot as a good luck charm and a convenient way to carry coins for phone calls. The penny loafer’s enduring popularity soon made it a timeless symbol of classic, effortless style.

Boat shoes Sperry Ivy League style menPin
From the dock to the city streets, boat shoes deliver a smart nautical flair. Photo: Sperry

Boat Shoes: In 1935, Paul A. Sperry designed boat shoes to provide traction on wet boat decks. By the mid-20th century, they had become a beloved casual wear staple among Ivy League circles.

With their durable leather construction and functional design, boat shoes embody a relaxed yet rese of style, perfect for everyday wear.

Suede driving shoes Aurélien Ivy League style menPin
Slip into style and comfort with suede driving shoes. Photo: Aurélien

Slip-on Shoes: like the classic driving moccasin, Slip-on shoes exude effortless elegance and convenience. Their laceless design effortlessly conveys a polished yet relaxed sense of style, aligning perfectly with the Ivy League’s understated sophistication.

Ivy Style Outfits

Casual Ivy League Outfit

Polo shirt outfit Ivy League style men white jeansPin
The polo shirt adds a polished look to the casualness of white jeans. Photo: Ralph Lauren

The epitome of casual Ivy League style is embodied in a polo shirt paired with jeans and loafers, a chic and understated combination.

For a modern twist, pair a classic polo with white jeans for a crisp, sophisticated look. Add loafers to complete the ensemble, and you’ll radiate a relaxed, put-together perfect for everyday wear.

Ivy League Formal Wear

Navy blazer outfit Ivy League style menPin
Embrace formal Ivy League style with a navy blazer, Oxford shirt, and chinos. Photo: Vineyard Vines

A cornerstone of the Ivy style is a well-tailored blazer, which instantly elevates an outfit with its timeless appeal.

Pair a classic blazer with a crisp oxford shirt, neatly pressed chinos, and loafers for a sharp, put-together look that exudes quiet confidence. This versatile ensemble is perfect for dressing up or adding a touch of sophistication to everyday wear.

Ivy League Sports Influence

Rugby shirt outfit Ivy League style menPin
Incorporate a sporty aesthetic into your Ivy League look with a rugby shirt. Photo: Mango

Ivy League style has its roots in collegiate sports, and one iconic piece that embodies its relaxed attitude is the rugby shirt.

Pair a classic rugby shirt with black jeans and loafers for a stylish, laid-back hat perfect for everyday wear. The horizontal stripes of the rugby shirt nod to Ivy League’s athletic heritage, while the black jeans and loafers add a sleek, modern touch.

And for a more formal occasion, throw on a rowing blazer to elevate the ensemble and add a touch of sophistication.

Modern Ivy League Brands

Fashion brands update Ivy League classics with modern colors, prints, and twists, balancing casual and formal. These revamped designs are easy to wear and style, blending heritage with innovation to keep the look fresh and fashionable.

Polo Ralph Lauren herringbone jacket Ivy League style menPin
Polo Ralph Lauren strikes sartorial favor with its classic herringbone jacket. Photo: Ralph Lauren

Ralph Lauren: Known for its Americana aesthetic, Ralph Lauren brings a modern twist to Ivy League classics. Their collections feature polo shirts, blazers, and sportswear that embody both elegance and casual cool.

J. Press striped sweater Ivy League style menPin
J. Press serves up a timeless ensemble with pleated trousers and a wide-striped knit sweater. Photo: J. Press

J. Press: One of the most storied Ivy League brands, J. Press has crafted some of America’s best jackets and blazers for over 100 years. Their commitment to traditional tailoring and quality has made them a cornerstoneLeaguey Leauge fashion.

Brooks Brothers white jeans Ivy League style menPin
From casual to formal, Brooks Brothers delivers Ivy League style in spades. Photo: Brooks Brothers

Brooks Brothers: As one of the oldest American clothing retailers, Brooks Brothers has been instrumental in defining Ivy League fashion. They offer various essentials, from dress shirts and suits to ties and casual wear.

Vineyard Vines quarter-zip Ivy League style menPin
With its whimsical spirit, Vineyard Vines injects a breath of fresh air into the traditional Ivy League style. Photo: Vineyard Vines

Vineyard Vines: This brand brings a playful and colorful approach to the Ivy League aesthetic. Known for their vibrant prints and relaxed styles, Vineyard Vines offers everything from polo shirts to chinos.

Tommy Hilfiger white polo shirt Ivy League style menPin
Championing its fashioned take on classic American cool, Tommy Hilfiger embraces Ivy League style fundamentals. Photo: Tommy Hilfiger

Tommy Hilfiger: Known for its classic American cool style, Tommy Hilfiger often includes elements like nautical stripes, bold colors, and smart casual wear. The brand’s collections frequently feature Ivy League staples such as blazers, chinos, and button-down shirts.

Textured sweater L.L. Bean Ivy League style menPin
L.L. Bean is known for its wardrobe essentials like crewneck sweaters. Photo: L.L. Bean

L.L. Bean: Renowned for its high-quality outdoor apparel, L.L. Bean’s Ivy League staples include Bean Boots, sweaters, and flannel shirts. Their rugged yet refined items have long been favorites on Ivy League campuses, especially for outdoor activities.

Reversible varsity jacket GANT Ivy League style menPin
GANT brings a contemporary look to the Ivy League aesthetic with its reversible varsity jacket. Photo: GANT

GANT: Originally a shirtmaker, GANT has evolved to offer a full range of clothing. Known for their high-quality Oxford shirts and innovative approach to casual elegance, GANT embodies the classic Ivy League look.

Long-sleeve polo Lacoste Ivy League style menPin
Lacoste is synonymous with the classic polo shirt. Photo: Lacoste

Lacoste: Famous for its iconic polo shirts, Lacoste has been a fashion staple since the 1930s. The brand’s timeless designs and commitment to quality continue to make it a favorite among those looking to embrace Ivy League style.

Harrington jacket Barbour Ivy League style menPin
With its renowned reputation for crafting exceptional outerwear, Barbour offers a range of timeless pieces. Barbour

Barbour: Known for its waxed jackets and quilted outerwear, Barbour adds a touch of British country style to the Ivy League wardrobe. Their durable, stylish pieces are perfect for a traditional look with a rugged edge.

Ivy Icon: JFK Style Inspiration

President John F. Kennedy shawl neck cardigan Ivy League style menPin
President John F. Kennedy photographed aboard the Honey Fitz in Hyannis Port, Massachusetts, with his daughter Caroline in 1963. Kennedy wore a shawl neck cardigan. Photo: By Cecil W. Stoughton (1920 – 2008) – Cecil Stoughton, White House Photographs NARA, Public Domain, Link

President John F. Kennedy’s style had a lasting impact on Ivy League fashion, blending sophistication with relaxed charm. At his family’s summer home in Hyannis Port, Kennedy’s casual style was effortlessly chic, popularizing nautical-inspired clothing, boat shoes, and loafers for a laid-back yet polished aesthetic.

President John F. Kennedy suit Ivy League style menPin
President John F. Kennedy pictured with Ambassador of Nepal, Rishikesh Shaha, in May 1961. Photo: By Robert Knudsen. White House Photographs. John F. Kennedy Presidential Library and Museum, Boston – https://www.jfklibrary.org/asset-viewer/archives/JFKWHP/1961/Month%2005/Day%2002/JFKWHP-1961-05-02-A, Public Domain, Link

Kennedy’s sartorial influence extended to his presidential attire, where he set a new standard for fashion with tailored, often bespoke suits that featured impeccable fit, narrow lapels, and natural shoulder lines.

President John F. Kennedy, Robert, Ted Ivy League style menPin

Kennedy’s sleek, modern suits were characterized by their clean-cut simplicity, often paired with slim ties and polished dress shoes in classic colors like navy, grey, and charcoal.

Pictured left, President John F. Kennedy poses for a picture with his brothers Robert and Ted in 1960. Photo: By United States Senate (invalid URL), Public Domain, Link

Kennedy embodied classic Ivy style, wearing tweed sports coats for sartorial flair, while his brother Robert paired his sports coat with a smart polo for a crisp, understated look.

Kennedy’s mastery of casual elegance was also evident in his everyday attire, where he balanced formal elements with relaxed pieces like soft knit sweaters, Oxford button-downs, and V-neck cardigans.

President John F. Kennedy Sweater Wayfarer Sunglasses Ivy League style menPin
Wearing a classic crewneck sweater and Wayfarer sunglasses, President John F. Kennedy sails aboard the U. S. Coast Guard yacht Manitou off the coast of Maine. Photo: Robert Knudsen, Public domain, via Wikimedia Commons

This refined yet approachable look was completed with signature accessories, including Ray-Ban sunglasses and slim, understated watches. Through his effortless style, Kennedy continues inspiring generations of men.

Modern Ivy Style

Rowing Blazers tartan suit Ivy League style menPin
Embrace a bold, modern Ivy League aesthetic with fashion brands like Rowing Blazers. Photo: Rowing Blazers

The Ivy style is characterized by clean lines, classic cuts, and a subtle blend of casual and formal wear. This aesthetic is often complemented by a classic, understated haircut, such as the Ivy League hairstyle, which adds to the overall sophistication.

Furthermore, with roots in traditional fabrics like tweed, seersucker, and Shetland wool, the Ivy League aesthetic has been adopted, adapted, and reinterpreted by cultures worldwide, from Japan and Asia to Europe, as a symbol of elegance, intellectualism, and social status.

A true classic, Ivy League style continues to inspire fashion, celebrated for its enduring appeal and versatility.


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