1920s-’40s

Leading Men: The Princetonians

When it comes to starting fashion trends, there’s Princeton and then there’s every other school. From the three-button suit to its namesake haircut, Princeton has popularized such menswear staples as Norfolk jackets, raccoon coats, tweed sport coats, rep ties, spectator shoes, khaki pants and Shetland sweaters. Princeton’s sartorial influence has been dulled by time, but


Phillips Academy Yearbook, 1942

This week I met with the new owners of The Andover Shop. First off, they can report that Charlie is hanging in there at the ripe age of 93. The team that took over has only modest upgrading plans, which mostly include a new website and perhaps some store events. Certainly no collaborations with Urban


Vintage Varsity

The first vintage costume event I went to — way back in 1996 — was the Bay Area’s Gatsby Summer Afternoon. Held at the Dunsmuir House, an estate in the Oakland Hills, the event features music and dancing, vintage cars, and a contest to see who can create the most opulent picnic spread. The event draws


Natural Style: Dartmouth in the ’40s & ’50s

A tour of Dartmouth College’s library in the 1950s, shown in the top video, sheds light on the school’s lifestyle and sartorial history. Male students seen hard at work wearing sweaters, flannels and thick trousers highlight two things: The lack of female students and a clear fashion sense unique to the college. Dartmouth did not


Birth Of The Cool

  This Esquire illustration was recently posted to Ivy’s Facebook group. It obviously has great visual appeal, but I found it especially interesting for the date: it was drawn in 1942. Now you can see the ’40s-era drape in the cut of the blazer and the trousers. And of course by the time the Ivy


Hold That Tiger

Lately we’ve been posting about Princeton and the Joe College years of the late ’20s. Now we combine the two with images from a Charleston-themed retro party held at Princeton in 1949. Arriving fashionably late in dad’s coonskin coat: This pair of twinkletoes were winners of the dance contest. Imagine what the losers looked like.


Campus Capers

In the ’80s it was the preppy look. A generation before that, the Ivy League Look. And a generation before that was the Joe College years. What they all had in common, besides some sartorial ingredients, was appeal to the broader masses, and in the case of the ’20s and ’30s, guys who’d never even


Classic ‘Rock

It’s long been said that Yankee frugality dictates that men hang on to their clothes, repair them as necessary, and pass them on to their progeny. Somehow I got hold of one when the owner wasn’t looking. It bears witness to the values of Ivy style: quality, smartness, practicality, longevity, thrift, stability. Custom made in


Joe College

J.C. Leyendecker’s first initials stand for Joseph Christian, but they might as well stand for Joe College. In a career spanning from 1900 until World War II, the American illustrator painted 300 covers for the Saturday Evening Post, as well as advertisements for products like Kuppenheimer Clothes and Interwoven Socks, that featured Harvard Rowers, Princeton football


Penny For Your Thoughts

Ivy Style’s Facebook group hit a milestone last weekend, surpassing 5,000 members, half of which want to strangle the other half by their necktie. And I don’t mean for not having a dimple. Or rather for having one. You get my point. Anyway, the imperturbable souls able to brave social media in 2018 (too strong




War And Peace

On this Memorial Day, here’s to all the men who never got the chance to attend college on the GI Bill — or live out the rest of their lives. We are grateful for their supreme sacrifice.  As for those who did go from storming the beach in Normandy to storming college classrooms, here’s a


Hooked On Vents

As a follow-up to our recent post on hook vents, here are two new finds from frequent comment-leaver Carmelo Pugliatti. The first shows a hook vent from the 1890s, when men carried walking sticks and wore bowler hats. Note the lapped seams as well. Below that is is a flash forward two-and-a-half decades later, to


Raccoon Season

Historically, Ivy style has always championed durability and functionality. Nowhere is this truer than in the realm of outerwear, where such weathered classics as the toggle coat and balmacaan remain viable and timeless. However, at certain vivacious moments in the style’s history, discerning collegiate sartorialists have exchanged the reliable for the resplendent, the austere for


Price Is Right

Iconic horror actor Vincent Price knew how a proper Yale undergraduate should dress in the 1930s. 



Camera Roll

Golden Age of Hollywood actor Robert Montgomery poses for the camera with ample roll: not only on the lapels of his ’30s-cut suit, but on his buttondown shirt collar as well. Wonderful example of Old Hollywood masculine glamor (with obligatory pipe and sleek hair) combined with the youthful nonchalance of a buttondown. Thanks to Ivy


Studied Carelessness, 1934

This is what passed for undergraduate nonchalance in 1934: three-piece suits, suspenders, lace-up shoes, topcoats and hats. From the January issue, here’s Esquire‘s take on the studied carelessness of collegiate style. — CC