1920s-’40s

Shades Of Tobacco

Tomorrow is International Pipe Smoking Day, so if you don’t have a pipe and tobacco, you can spend your Sunday afternoon procuring them. And you’d better hurry before it’s illegal. Pictured here are two undergrads with tobacco-colored tweeds as depicted in a 1936 issue of Esquire. Here’s to our fellow men of the pipe. —

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From The Archives



Esquire’s Academic Clothes Curriculum, 1947

Yesterday Esquire announced that David Granger is out as editor after helming the magazine for nearly 20 years. His replacement is Jay Fielden, who had been overseeing Town & Country. Will Esquire return to the way it was from the ’30s to the ’60s? Not likely. All the more reason to put your subscription money


Comfort And Neatness, 1949

From the September, 1949 issue of Esquire. Subscribe to the digital archives here. From the University of Maine to UCLA, college men spend most of their time pounding the books in class, in the dorm, or in the library with Miss Distraction of 1949. Their keynote is comfort and neatness. The fellow in the window


Saddle Shoes And Kilties, 1941

What do saddle shoes and kilties have in common? They’re both featured in the Laurence Fellows-penned image above from the Esquire archives, and they’re both not on my Christmas list. Regular readers will know my aversion to both footwear atrocities. But then again I dig bit loafers. De gustibus, et cetera, et cetera. Below is


It’s 1940 All Over Again

Chris Sharp found these images in the same Esquire issue featured in our last post: September 1940 (sign up for the archives here.) They should provide further inspiration for any of you who feel stuck in a sartorial rut. The text for the top image described this college man as wearing the color combination of


Weejuns Go With Everything, 1940

This image (another find by comment-leaver Carmelo in the Esquire archives), came with a date but no caption. So I decided to give it one for the headline above. It’s easy to think of penny loafers as a casual shoe since, in the grand footwear scheme of things, they are. But much of the charm


Glad-Time Night In Tigertown, 1942

What to wear with a rep tie and OCBD? How about a plaid tweed jacket and a windowpane vest? There were so many options during the Golden Age Of Ivy, even while there was a war going on. Cheers to Chris Sharp for spotting this 1942 illustration from the Esquire archives, which you can access


Heavy Program, 1946

An encore from Esquire in the year 1946 (head over here to access the archives for a mere $4.99 per month). According to the text, the student on the left has a tweed suit cut in “conventional three-button style and easy lines.” The other fellow “sticks to the regulation two-tone saddle-strap shoes, checked tweed jacket


Tweeds On The Books, 1946

The war was over and the boys were already back in school. This is from the Esquire archives, which recently went online and can be accessed for a mere $4.99 per month. Ivy Style Facebook member and comment leaver “Carmelo” found this image from 1946, which features some of my favorite things: blue buttondown, grey



Ideal For Lounging About: Bass Weejuns, 1936

It’s already time to dip into the Esquire archives again. This one was spotted by Marc Chevalier, walking menswear encyclopedia and member of Ivy Style’s Facebook group. The ad above dates to August 1936, less than one year after Esquire had helped introduce the Bass Weejun to the nation. Two months later, there was this


What Is The Origin Of The Two-Button Cuff?

The Masters golf tournament gets underway tomorrow, and so in the interest of timeliness we present the above photo to fuel historic conjecture. The photo is of Ernest Jones, one of the most famous early golf instructors and author of the classic tome “Swing The Clubhead.” Jones was an Englishman who lost a leg in


Brooks Civvies: The New Yorker, 1945

Perhaps the heyday of the Ivy League Look began not in the ’50s, but the moment after World War II’s detente. In this 1945 New Yorker cartoon, a soldier returns home from the war and is told by his mother to immediately get himself some mufti at Brooks Brothers to show that everything is all


White Friday

  Stuff your stocking with stocking ties from White of New Haven.