Past Paper: How to Be Right on Top

We’ve worn vintage clothing for decades. We’ve not owned a contemporary suit since college, and over the years we’ve built up an extensive collection of neckties and bowties (we even taught ourselves to tie a bowtie—no clip-ons for us) from the 1930s, ’40s, and ’50s. We also have more 1940s, ’50s, and early ’60s casual shirts, both long-sleeved and short-, than we can count (or find a place to store, much to Ms. Cladrite’s chagrin).

Our eyeglasses are vintage, as are our sunglasses.

We’ve even taken to wearing sock garters, as was once done, when we’re dressed to the nines.

In short, we’re committed to the vintage look of the pre-Mad Men era. It’s our preferred style, and has been for some thirty years.

And yet, until two or three years ago, we couldn’t bring ourselves to wear a fedora.

Mind you, we loved the look, always keeping an eye out for the various styles of hats that appeared in the dozens of old movies we watch a year. We even owned a fedora, a vintage model in wool, not fur, felt (not that we knew the difference then) that we’d purchased many years ago, but it was too snug to wear comfortably or often.

But we weren’t entirely sure we could pull off wearing a fedora, anyway, much as we wished we could. We didn’t know what style, material, color, brim width, or crown height would suit us. Heck, truth be told, we didn’t even know those were questions to be considered. And we were convinced (we still suspect it’s true) that a certain level of self-confidence was required to look sharp in a fedora these days.

But now it’s a rare occasion on which you’ll catch us bareheaded. We’re devoted hat wearers — fur felt fedoras in the fall, winter, and spring; straw Panama style hats in the summer.

Nowadays, you see lots of young folks, guys and gals, wearing hats — stingy-brimmed fedora-esque numbers of paper straw or cloth.

Perhaps you’ve been tempted yourself to don one. We encourage you to do so, by all means. But buy a real hat, one that will last you and look sharp for years to come—not one of these $5 or $10 cheapies you can pick up on the street or at some “hip” store at the mall.

Here’s a helpful brochure from 1950 that we think you’ll enjoy looking over. And when you’ve read it, you’ll know a lot more about hats than you did. Perhaps it’ll even give you the courage to take the plunge into hat ownership. Take it from us, you need only the nerve, the attitude, to pull the look off. Wear a hat like it’s the most natural thing in the world to you, and it will appear just that way to anyone you encounter. (P.S. The brochure requires the Shockwave plug-in; if it’s not working for you, you can download the brochure in PDF format here.)

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