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Ivy League Outfit Ideas for an Old Money Collegiate Look

With roots in the elite educational institutions of the American Northeast, The Ivy League style has been an emblem of preppy, old-money fashion for decades.

The Ivy League look depicts a lifestyle of affluence and privilege, a world of private schooling, yachting, and polo-playing, and is an unmistakable indicator of social status.

The style’s consistent use over the years by those in upper echelons underscores its enduring appeal and cultural significance as more than just fashion but a strong representation of heritage and refined taste.

In this article, we’ll offer young gentlemen insight into curating an Ivy League wardrobe to reflect a silent luxury, timeless style by providing outfit suggestions rich in history and cultural significance.

1. Ivy League Rugby Look

Ivy League Rugby shirt style

This Rugby-inspired outfit is a sartorial nod to Ivy League’s blend of relaxed and formal, suggesting a young gentleman’s transition from academic pursuits to social engagements while maintaining an air of old-money sophistication.

Start with a brown tweed blazer from a heritage brand such as Harris Tweed or Brooks Brothers.

Underneath, wear a mustard and navy striped rugby shirt from Ralph Lauren or Thom Browne to add a collegiate vibrancy to the outfit.

Ivy League Rugby style Male

The shirt is layered over a white Oxford button-down shirt from Gant or J. Press and an animal pattern necktie from Vineyard Vines, known for their repp ties with playful motifs.

Anchor the outfit with well-tailored khaki chinos from Dockers or Bonobos, representing the perfect blend of casual, smart, and top-sider shoes from Sperry for a nautical old-money lifestyle.

Finish the look with a leather braided belt from Anderson’s or Polo Ralph Lauren as a textural element that complements the tweed blazer.

2. Ivy League Uniform Look

Ivy League Uniform style

This Ivy League-inspired College Uniform look depicts the classic academic style, ideal for young gentlemen attending prestigious events.

Begin with a single-breasted navy blazer from a respected brand like Ralph Lauren or Brooks Brothers in a deep navy color and traditional cut to convey a sense of academic authority.

Ivy League Uniform style

Match with a white Oxford cloth button-down shirt from Gitman Vintage and a repp tie from J. Press or The Tie Bar, featuring club colors for a touch of collegiate flair.

Add a full-grain leather belt from Allen Edmonds or Trafalgar in a brown shade that complements the leather brogues and well-tailored khaki chinos from Bills Khakis.

Complete the look with burgundy leather brogues (or walnut brown) from an esteemed English shoemaker such as Church’s or Crockett & Jones.

3. Ivy League Rowing Look

The Rowing Blazer Ivy League style

Blending traditional Ivy League activities with a touch of sporting flair, this Rowing-inspired preppy outfit captures the essence of a dapper gentleman.

Start with a burgundy rowing blazer from Rowing Blazers, known for its authentic and chic take on classic boating jackets.

Ivy League Style Rowing Look

To enhance the collegiate aesthetic, pair with a white Oxford cloth button-down shirt from Brooks Brothers and a Ralph Lauren repp tie in a complementary color and pattern.

Continue with a canvas D-ring belt from a preppy staple like Smathers & Branson and well-fitted khaki chinos from a quality maker such as Bills Khakis or Incotex to balance the rich color of the blazer.

Complete the look with canvas lace-up shoes in a deep red hue from Sperry or Superga.

These shoes echo the blazer’s color and lend a casual, sporting touch to the refined outfit.

4. The Waspy Graduate Look

Ivy League College Style Cardigan look

This Ivy League-inspired outfit, coined “The Waspy Graduate Look,” epitomizes the quintessential style of a young, affluent gentleman ruling the academic world.

Begin with a rich, burgundy cable knit V-neck sweater vest from a heritage brand like Polo Ralph Lauren or J. Press over a white Oxford shirt from Brooks Brothers.

Waspy Graduate Look Ivy League style outfit idea

Complement the sweater vest with a contrast trim V-neck cardigan in forest green and navy from a collegiate outfitter such as Rowing Blazers or Gant, adding depth and a modern twist to the classic aesthetic.

Accessorize with a traditional repp tie in a stripe pattern from a preppy mainstay like Vineyard Vines and chinos from Bills Khakis to reinforce the Ivy League theme.

Complete the look with striped socks in school colors from Ralph Lauren and Old Money dress shoes from Church’s, cementing the refined yet youthful appeal of “The Waspy Graduate Look.”

5. Ivy League Baseball Look

Ivy League Baseball Varsity Jacket style

This Baseball-inspired look pays homage to the timeless American pastime while maintaining a sophisticated and scholarly appearance.

Start with a classic navy baseball cap featuring a collegiate letter or team logo, such as one from Ebbets Field Flannels, to set the sporty tone.

Ivy League Baseball Varsity Jacket style

Continue with a white Oxford shirt from a traditional Ivy League outfitter like Gant or Gitman Vintage beneath a trim cardigan in teal and orange from Polo Ralph Lauren, reminiscent of vintage varsity sweaters.

Add a repp tie in a complementary colorway from a preppy accessories label like J. Press and a black leather dress belt from Allen Edmonds or Martin Dingman to showcase school spirit.

For a touch of textural interest and seasonal appropriateness, wear white oatmeal linen dress pants from Sid Mashburn.

Finish with white crew socks from Pantherella and black Oxford shoes from Alden or Johnston & Murphy.

Ivy League-Inspired Old Money Style Masterclass

Mastering the Ivy League-inspired old-money look is about curating a wardrobe filled with enduring classics that have stood the test of time.

From tailored blazers to Oxford button-downs, these timeless garments form the foundation of a sophisticated and refined aesthetic.

Whether attending a college reunion, a charity gala, or a weekend getaway to the Hamptons, The VOU’s style experts will ensure you’re impeccably dressed for every occasion.

Embark on your journey to mastering the art of Ivy League-inspired old money style with The VOU’s personalized styling services and make lasting impressions in any setting.

Embrace the legacy of Ivy League style and book your consultation with The VOU today to achieve an authentic old-money look that will set you apart from the crowd.

With over twenty years of front-row fashion and styling events, collabs with haute-couture houses, and a PhD in Luxury Fashion, Laurenti is an expert in crafting personalized looks that depict old-money sophistication.

With years of expertise in high-end fashion collabs and a PhD in Sustainable Fashion, Ru specializes in curating eco-luxe wardrobes for the modern gentleman seeking understated refinement.

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