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A League of Their Own

“With the Ivy League Look reaching full fruition in the 1930s and ending as a current and relevant fashion in 1967, its full flowering spans just three decades. Indeed, there are more years that have passed since the end of the heyday than the years from codification to heyday’s end.”

“However, the silver age also cemented Ivy’s legacy in the “classic” and “timeless” sense. It continues — by whatever name and in iterations that conform with contemporary style — to be worn by anyone with the taste for it. And good taste should be available to anyone with the sensibility to appreciate it.

Christian Chensvold, The Rise And Fall Of The Ivy League Look


Some of America’s most influential sartorial movements were born and bred in the middle of the 20th century at universities across the States. Take inspiration from such men as you consider a few of our history’s most venerable and iconic looks.

Dapper Dress

Enthusiasts really seem to enjoy a good debate between the nuanced differences of the American style traditions of “Ivy/preppy/trad/whatever”. But as the influential anchors of each category are quite similar, we’re going to simplify things a bit. From penny loafers to sack suits and oxford button downs to rep ties, there is a rich sartorial tradition (albeit a somewhat stodgy one) when it comes to Northeastern, upper-middle-class collegiate style. But in its time, it wasn’t stodgy at all.

More important than the Ivy Style ingredients was the spirit of those who wore them. With each new decade, J Press and Brooks Brothers would manufacture items favored by college men, but it was the young men themselves that showed how it could be worn, establishing over time what would ultimately be accepted as “Ivy League”. Worn un-ironed and frayed with nonchalance, the true pioneers of Ivy League were not actually conforming to a standard but pioneering a new one.

With that said, we don’t recommend duplicating the outfits of Yale undergrads during the interwar years with historical accuracy. Rather, grab some of the influential ingredients of their wardrobe (not to mention their spirit) and mix them up with your favorite office-appropriate sneakers or monk-straps to pave your own inspired vibe.

Be they traditionally Ivy League (oxford cloth button downs), ‘80s collegiate (varsity jacket), or modern day classics, mix to your heart’s desire. At its time, the Ivy League Look was an expression of culture. Yours should be too.

The Softer Side of Swag

For those with a particular penchant toward all things casual, there’s an Ivy League for that, too. In 1865, Harvard’s baseball team embroidered a large ‘H’, centered on a gray flannel shirt, and the “Letter Sweater” was born. It quickly became common practice for captains to allow only those individuals that played in the most significant games to keep their jerseys over the off season, making possession of the letter a signifier of exclusivity and prestige.

It’s adapted over the years into a near infinite variety of iterations, but the aesthetic is ubiquitous and timeless. From streetwear to high fashion, there’s an eclectic appreciation (and therefore unique expression) for the letter.