Uptown, to the Collegiate School for boys — founded in 1628, the oldest school in America, JFK Jr., and all of that — with my plaid sport coat, my Ivy-inspired oxford, and my striped boat shoes.

Here are the best preppy clothing brands on the market. Shop the preppy aesthetic from popular brands like Ralph Lauren, J.Crew, Lands' End, and more.

Suddenly, clothes that were as sexy as they were preppy made perfect sense. ... they had to borrow from the boys. (Brooks Brothers didn’t even launch a women’s department until 1976).

The preppy style of the '50s, '80s, and '90s is timeless. Here, take a look at preppy style evolution and get tips on how to wear it today.

Fred Perry, a brand known for preppy streetwear, has been associated with far-right groups since shortly after it was founded in 1952, as many historians have pointed out. Most recently, its $95 ...

How ‘Ivy’ clothes became a century-spanning fashion mainstay “Ivy was a huge clothing phenomenon in the mid-20th century,” said Avery Trufelman, host of the podcast “Articles of Interest ...

Style Points is a weekly column about how fashion intersects with the wider world.. Lisa Birnbach has seen this all before. The author of The Official Preppy Handbook, which went old-world viral ...