People often say that fashion goes in cycles. Things that were once forgotten eventually coming back into style. Men across the world have become more interested in traditional clothing in the last several years. The Ivy League and preppy styles that were popular in the middle of the 20th century are once again affecting how men dress today. 

The Ivy League Look 

In the 1920s and 1930s, Ivy League style initially appeared on the campuses of top American institutions. By the 1950s, this was the most popular way for men to dress smart casual. The outfit was a mix of classical tailoring and sportswear that was designed to be worn every day. Blazers, Oxford shirts, chinos, loafers and knitwear were all must-haves. The Ivy League jacket had a loose fit, with smooth shoulders and a three-button roll that made it hang naturally.  

This approach was different from strict formality. It was fitted but comfy and it was stylish but useful. People wore the Oxford cloth button-down shirt (OCBD) with suits and blazers. It was first made for polo players. Penny loafers and brogues supplanted the more formal Oxford shoes. Khaki chinos, which were acquired from military excess during World War II, are now a permanent part of Ivy League clothing.  

President John F. Kennedy became a symbol of this style, showing how easy it was to wear traditional tailoring. His impact helped the Ivy League look move from college life to everyday dress. 

The Rise of Preppy Style 

By the 1960s, Ivy League style had changed into what people called “preppy” style. The mood was lighter, but the essence stayed the same. Chinos came in more than just beige and grey; they also came in colourful colours. Polo shirts and sweaters with cable-knit patterns became important parts of the wardrobe. Casual chic started to take the place of formal neatness, yet it still looked polished.  

People started to think of preppy style as being about leisure, sailing, tennis and summer vacations. It stood for comfort, tradition and luxury. By the end of the 20th century, it had become a well-known style of men’s clothing that was different from but closely related to the Ivy League appearance. 

Pop Culture and Revival 

Movies and TV shows have done a lot to bring these forms back. Shows like Mad Men showed off the sharp tailoring of the 1960s, which made people want to wear tight suits and narrow ties. Peaky Blinders showed how cool heritage tailoring can be with waistcoats, pocket watches and newsboy caps. Suits had an impact on a generation of young professionals who liked the clean lines and confidence of corporate power dressing.  

Younger people have rediscovered the elegance of old-school menswear through these portrayals. What used to only be in history books is now on runways, social media and in everyday clothes. 

The Indian Connection 

Indian males are part of this worldwide rediscovering. Streaming services, international periodicals and online fashion content have all introduced Western-style trends to people in cities. A lot of people want to be like the people in these stories. They indicate that clothes are a sign of success, intelligence and being unique.  

Young professionals in cities like Mumbai, Delhi and Bangalore are buying classic pieces that are influenced by Ivy and preppy styles. People now like crisp shirts, fitted blazers and flexible chinos more than short-lived seasonal trends. This shows that people are moving toward clothes that have cultural significance and will last a long time. 

Why the Comeback Matters 

Old-school fashions are popular today because they are more than just trendy. They show a way of thinking. The Ivy League style shows that you value history and learning. The preppy style says that you have money and free time. Both show refinement through their simplicity.  

A lot of men these days want clothes that will last, not clothes that go out of style quickly. They like clothes that are simple and elegant, that can be used for work, travel and social events. That’s exactly what old-school menswear does. It lets men make wardrobes that are classy, flexible and never go out of style. 

Cirocco’s Role in Classic Menswear 

We at Cirocco think that the return of Ivy League and preppy designs shows a deeper truth: real style comes from using high-quality materials and doing careful work. When a man buys a blazer made of excellent wool or a shirt made of high-quality cotton fabric, he is not only buying something nice to wear, but also something that will make him feel good about himself and his heritage.  

Cirocco produces luxury fabrics that are the basis for these traditional styles. We help guys who want to dress in a way that is both classic and modern, combining tradition with modern style. Our high-end fabrics bring the Ivy League look and the preppy renaissance to life in a unique way for guys who like these classic trends. Get in touch with us if you want to style like a proper gentleman.