Ivy League Style Guide to Master the Classic American Look

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What is Ivy League Style?

Ivy League style is a distinct way of dressing with origins in the early 1900s uniforms of elite Northeastern United States preparatory schools and universities.

The early American institutions were built around the British educational system (attire and activities), and the Ivy League style followed the aesthetics of traditional British preparatory schools.

Ivy League Style

Initially, the Ivy League style was casual, dressing against the time’s traditional styles (Trad styles).

Nowadays, the Ivy League style is seen as a conservative but refined way of dressing, reflecting the Preppy subculture’s elitism and affluent lifestyle.

Ivy League Style

Ivy League Style Origin

The Ivy League style originated in New England, a northeastern region of the United States and home to Ivy League universities, comprising the states of Maine, Vermont, New Hampshire, Massachusetts, Connecticut, and Rhode Island.

Inspired by ‘Ivy Day’ – the ceremony of planting ivy at New England colleges, sportswriter Stanley Woodward coined the term ‘Ivy League’ in 1933 to describe colleges with similar athletic programs.

How to Dress Ivy League?

To successfully pull off the classic Ivy League look, you must understand the core components of the style: clothing, footwear, and accessories.

How to Dress Ivy League
Ivy League Style

It is also critical to know which Ivy League clothing brands to shop for and how to combine garments, footwear, and accessories.

Finally, how to match colors and patterns to exude sophistication without appearing formal while retaining the style’s aesthetic origins.

Ivy League Style Clothing

1. Sack Suit Royal Navy Blazers

Three-button single-breasted blazers in navy color with aesthetic roots in British naval attire.

Best for: corporate meetings, job interviews, and academic presentations

Recommended Brand: Brooks Brothers, Ralph Lauren

Knit Double-Breasted Blazer Regular fit, Double-breasted Navy Blue Club Blazer

2. Oxford Cloth Button Down Shirts (OCBD)

American adaptation of traditional British polo shirts in thick cotton Oxford cloth and button-down collar.

Best for: office settings, business-casual dinners, and under a blazer at academic events

Recommended Brand: Gant, Tommy Hilfiger, Ralph Lauren

Relaxed Fit white Oxford Shirt Slim Fit Stretch Oxford Shirt

3. Polo Shirts

Initially designed for tennis players, the ideal Ivy League polo shirts are short-sleeved from cotton piqué knit with a collar and two or three buttons.

Best for: Fridays at the office, weekend brunch, and summer garden parties.

Recommended Brand: Lacoste, Ralph Lauren, Lilly Pulitzer

Short Sleeved polo shirt Women’s Organic Cotton Terry Polo

4. Khaki Chinos

With roots in the uniforms of the British and French military, Ivy League chinos are straight-legged, flat-front trousers made from twill fabric.

Best for: business-casual office events, weekend errands, and family gatherings

Recommended Brand: J Crew, Gant

Sailor heritage chino pant Slim Fit Chinos

5. Nantucket Reds

Straight-legged casual trousers (or shorts) from canvas and dyed in a specific shade of red, designed to fade over time to a unique salmon color specific to Nantucket’s sailing culture.

Best for: coastal vacations, yacht outings, and summer barbecues

Recommended Brand: Murray’s Toggery Shop

Nantucket Reds Ivy League Trousers Nantucket Reds Ivy League Trousers

6. Plaid Skirts

Knee-length skirts made of Wool, with plaid or tartan patterns with aesthetics from the Scottish kilts.

Best for: school uniforms, church services, and academic ceremonies

Recommended Brand: Tommy Hilfiger, Ralph Lauren, Vineyard Vines

Tommy Plaid Skirt Polo Ralph Lauren Plaid Skirt

7. White Pleated Tennis Skirts

Initially designed for comfort and to allow movement while playing tennis, these short, white skirts with pleats are quintessential to Ivy League style.

Best for: tennis matches, summer picnics, and beach outings

Recommended Brand: Lacoste, Tory Burch

Lacoste Tennis Skirt Tory Burch Tennis Skirt

8. Cable-knit V-neck or Cardigan Sweaters

Wool or cashmere sweaters weaved in ‘cable’ patterns – a raised, textured surface – available in V-neck and button-up cardigan styles.

Best for: autumn gatherings, casual Fridays, and holiday dinners

Recommended Brand: Ralph Lauren, Lacoste

Ralph Lauren Cable-knit V-neck Sweater


Cable knit Cardigan Sweater

9. Flannel or Madras Sportcoats

Flannel sportcoats made of soft, brushed wool or cotton are ideal for colder weather, while Madras sportcoats are more suitable for warm weather, given their lightweight and colorful construct.

Best for: semi-formal events, office settings, outdoor social events, garden parties, or daytime weddings.

Recommended Brands: Brooks Brothers, Ralph Lauren

Ralph Lauren Flannel Madras Sport Coat Brooks Brothers Madras Sport Coat

10. Varsity Jackets

With a body made of wool and leather sleeves, these casual jackets feature front snap-button closures and embroidered team patches or school logos.

Best for: college sporting events, social gatherings at friends’ homes, or casual walks around campus.

Recommended Brands: J.Crew, Gant, Tommy Hilfiger

Gant Varsity Jackets Tommy Varsity Jackets

Ivy League Style Footwear

1. Penny Loafers

Slip-on leather shoes with a distinctive slot on the front – a reminiscence of the early days when Ivy League students used it as a penny holder.

Best for: academic settings, semi-formal dinners, and business-casual office environments.

Recommended Brands: G.H. Bass, Sperry

ghbass Weejuns Penny Loafers Sperry Penny Penny

2. Brogues

The Irish and Scotish-inspired low-heeled leather shoes have beautiful decorative perforations and serrations initially designed to let the water drain faster while walking through bogs.

Nowadays, Brogue-style shoes are considered ideal for business-casual and formal settings.

Best for: business-casual events, formal dinners

Recommended Brand: Thom Browne, Alden

Thom Browne Brogues shoes Alden Brogues shoes

2. Tennis Sneakers

Low-top leather sneakers with flat soles designed for optimal grip on tennis courts.

Best for: tennis matches, part of casual Ivy League outfits, country club lawn games, and relaxed outdoor brunches.

Recommended Brand: Lacoste, Tory Burch

Lacoste Tennis Sneakers Tory Burch Tennis Sneakers

Ivy League Accessories

1. Striped Ties

Classic ties with diagonal stripes in contrasting yet subdued colors with aesthetics rooted in traditional British clubs that used ties as visual group signaling.

Best for: formal events, jobs in law or finance, to accessorize business attire

Recommended Brand: Brooks Brothers, Ralph Lauren

Ralph Lauren Ivy League Striped Tie Gant Ivy League Striped Tie

2. Needlepoint Caps

Needlepointing – a New England crafting tradition – is the art of applying intricate designs or motifs featuring collegiate or traditional symbols by hand.

Best for: outdoor sporting events, barbecues, campus days

Recommended Brands: Harding-Lane, Gant, Tory Burch

Gant Needlepoint Ivy League Baseball Cap Tory Burch Needlepoint Ivy League Baseball Cap

3. Needlepoint Belts

Artisanal quality, hand-stitched belts featuring detailed stitching, intricate designs, and motifs like animals and flags.

Best for: garden parties, country club gatherings, or casual Fridays at work

Recommended Brand: Ralph Lauren, Smathers & Branson

Ralph Lauren Needlepoint Belts Ralph Lauren Needlepoint Belts

4. Knee-high Socks

Rooted in the school uniforms of British preparatory schools, knee-high socks transitioned into Ivy League style as a complement to formal wear and sporting attire.

Best for: formal events where full traditional attire is required

Recommended Brand: Brooks Brothers, Lacoste

Lacoste Knee-high Socks Alo Yoga Knee-high Socks

5. Argyle Pattern Socks

Originating from the tartans of Clan Campbell of Argyll in western Scotland, the argyle pattern became a symbol of sophistication in the 1920s when adopted by English and then American preppy culture.

Best for: Suited for semi-formal gatherings and day-to-day office wear

Recommended Brand: J Crew, Gant

Gant Argyle Socks J Crew Argyle Socks

4 Ivy League Outfit Ideas

Now that you understand the most relevant clothes, footwear, and accessories you need to put together an Ivy League look, here are four excellent outfit ideas to get inspired by.

Outfit Idea 1: Alumni Star

Ivy League Outfit
Ivy League Outfit: Oxford Cloth Button Down Shirt, Cable-knit V-neck Sweater, Sack Suit Royal Navy Blazer, Plaid Pleated Skirt, Argyle Pattern High Socks, High Heel Oxford Shoes

The star garment of this ensemble is the sack suit royal navy blazer; layered over a cable-knit V-neck sweater and an Oxford cloth button-down shirt, the blazer offers textural contrast.

The plaid pleated skirt and the argyle pattern high socks give the outfit a dash of femininity and a pop of pattern.

Finish the outfit with a dark leather pair of high-heeled Oxford shoes to create an air of polished refinement.

Outfit Idea 2: New England Vibes

Ivy League Outfit, Oxford Cloth Button Down Shirt, Flannel Sportcoat, Khaki Capri Chinos, Penny Loafers
Ivy League Outfit: Oxford Cloth Button Down Shirt, Flannel Sportcoat, Khaki Capri Chinos, Penny Loafers

The central piece of this outfit is the red and black flannel sportcoat in a dual tone, which gives it a pop of color while remaining within the bounds of preppy elegance.

Pair it with an Oxford cloth button-down shirt and khaki chinos for a tailored Ivy League appearance.

Completing the outfit with penny loafers in a matching red with the sportcoat to create a trendy look.

Outfit Idea 3: Campus Chic

Ivy League Outfit
Ivy League Outfit: Needlepoint Baseball Hat, Cropped Polo Shirt, Varsity Jacket, White Pleated Tennis Skirt, White Sneakers

In a nod to the quintessential Ivy League style, the cropped silhouette of the mini varsity jacket adds a contemporary twist appealing to fashion trendsetters and influencers.

Pair a white pleated tennis skirt, a cropped polo shirt, and a needlepoint baseball cap to bring a sense of sporty edge to the ensemble, and finish the look with classic white sneakers.

Outfit Idea 4: Yacht Club Queen

Ivy League Outfit
Ivy League Outfit Oxford Cloth Button Down Shirt, Madras Sportcoat, Brown Leather Belt, Nantucket Red Pants, Penny Loafers

With patchworks of blue, red, and white, the Madras sportcoat steals the show in this ensemble, adding a layer of sophistication and traditional Ivy League appeal.

Beneath the sportcoat, the Oxford cloth button-down shirt and the Nantucket red pants provide a timeless foundation, matching the coat’s colors to reinforce the look of Ivy League style.

Complete the look with brown penny loafers and a matching belt to create an outfit ideal for upscale weekend events like yacht club gatherings or seaside sunset dinners.

Ivy League Similar Styles

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Professional Styling Advice

Are you looking to improve your fashion style and unsure where to start? Are you into relaxed-casual, E-girlY2K, or VSCO looks, but the Ivy League style resonates with you, and you wonder why?

Contact The VOU’s Style Experts to receive your free and personalized styling advice based on your current way of dressing, preferred outfits, colors, aesthetics, age, gender, body shape, location, and event you seek to attend.

Your dedicated stylist will meticulously select essential garments, footwear, and accessories to craft a wardrobe that complements and enhances your style.

Take advantage of this unique opportunity to experience a transformative fashion adventure, all at no cost to you.

After years of managing hundreds of fashion brands from London's office of a global retailer, Mandy has ventured into freelancing. Connected with several fashion retailers and media platforms in the US, Australia, and the UK, Mandy uses her expertise to consult for emerging fashion brands create top-notch content as an editorial strategist for several online publications.

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