Historic Images

Try to be less grumpy!

As a follow-up to our last post on Taylor-Made shyoes, here’s another Main Street retailer that used the term “Ivy League” in its ad copy once the look became popular. These two Stetson ads are from 1953 and 1955 (coincidentally the same years as the Taylor-Made ads). Thanks to frequent comment-leaver “Old School” for alerting us …

Once the Ivy League Look gained popularity during the silver age of the ’50s, Main Street clothiers used the term as an advertising buzzword. Needless to say, Brooks Brothers and J. Press never had to resort to the term, and in fact dismissed the term “Ivy League” with mild scorn, as they’ve always done with …

A couple of weeks ago we posted a collection of vintage Dexter advertisements, and now here’s an interesting follow up. In 1968, as the Ivy League Look was plummeting in popularity, the shoe that would cement itself as a preppy staple in the 1970s was gradually garnering greater attention.  The above ad is from The …

If you hold a mirror up to your computer screen, you’ll see that the gent being measured for a jacket is at the venerable clothier Chipp, as seen in this illustration from the company’s 1965 catalog. Ivy Style asked Paul Winston, son of the Chipp founders, for any insight on the drawing, and he replied, “The …

Today Ivy Style extends warmest wishes for a happy International Men’s Day, with a little help from Harvard’s theatrical troupe The Hasty Pudding Club.  The above image dates from the 1880s, when men were men. 

This Norman Hilton advertisement dates from 1958. The copy includes the phrase “comfortably distinctive,” which is a good description of the Ivy League Look in general. Being distinctive while still comfortable is much more challenging, alas, when not wearing a flannel suit and soft-roll collar. But let the principle guide us nevertheless.

Back in 2011 I wrote a little piece on the navy blazer for Gilt MANual, calling it the Swiss Army Knife of tailored jackets. And yes, I’ve actually worn it as a warm-up jacket to the tennis court. That’s probably a bit affected, but it was rather enjoyable, and probably for that reason. One thinks of …

For Election Day 2020, here’s trivial troika of retro diversions. First up is the Kennedy clan in 1960, looking concerned when the outcome was still undecided. Perhaps JFK was humming our second vintage distraction, the Kingston Trio’s signature song “Worried Man”: And thirdly, from the previous election cycle of 1956, we have the debut cover of …

This interview originally ran in 2011, but the historic information on Gant, one of the most celebrated brands of the Ivy heyday, has evergreen value, and so today we pay it a revisit. * * * With fashion in a constant state of flux, it’s no wonder apparel brands are less than assiduous when it …

Today we feature a random assortment of vintage images that have been lying around in an old shoe box, metaphorically speaking. And yes that’s a pun on “shoe;” after all, some of these images are from Yale.   This one, however, is from an altogether different kind of campus shop:   College men were once …