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Mad Men Style: 1960s Fedoras

Today on This Week’s Look, we are sipping afternoon mimosas on the lanai and talking men’s hats. Specifically, vintage 1960s stingy brimmed fedoras, trilbys and Homburgs. Think Leonardo DiCaprio in “Catch Me if You Can.” Sammy and Frank vacationing in Palm Springs.

But enough about Leo, Sammy and Frank, let’s talk about my amazing Harold. He is a hat man. Correction: He is THE hat man. Among other things. And I am, of course, a hat woman, so it is only natural that I should fall in love with a man who can pull off a hat every day of the week. In fact, he is such a natural, I suspect the nurses put a wool felt fedora on him when he was born rather than one of those snuggly newborn skull caps. He is French after all, so one can never be sure what goes on over there. Harold’s hat collection isn’t necessarily staggering. That is to say, his collection will never rival mine in sheer numbers, but it is robust enough to provide a hat for just about any occasion.

Back to my original thought. 1960s trilbys. These short-brimmed hats are destined to become ubiquitous once the new season of Mad Men premieres next year, so if you’re in the market for one, I would do my shopping now before the rise in demand and prices follow. There are some amazing, original 1960s toppers out there right now, and we have selected some of the best for our readers. Click on each image below to see the full listing.

Vintage 1960’s Alexander wood tweed trilby, size 7, on eBay. Current bid $29.43.

Vintage 1960s mustard wool felt stingy brim fedora. Buy it Now for $53.85 on eBay, or make an offer.

Vintage 1960s, never worn, light blue and taupe houndstooth hat by Dobbs. Size 7 1/4 – 7 3/8. Buy it Now for $54.99 on eBay, or make an offer.

Vintage straw topper, size 7 1/8, from HartsCloset on etsy. $44.99.

Vintage 1960s fine fur or cashmere dark charcoal trilby from StyleStash on etsy, size 7 1/8. $160.

Vintage 1960s The Stetson “Playboy” in delicious fur with ridiculously cool gold ornament on the band. Size 7. Buy it Now for $132 on eBay, or make an offer.

Vintage 1960s “pocket fedora” by Knox, size 7 1/8. This dark green pocket hat is a straightforward business. Fold it up, stick it in your pocket and it will hold its shape brilliantly. Matching nylon hat band adorned with bright red feather. $79 on eBay.

Rare raw silk stingy brim fedora from NorthStarAtelier on etsy. $75.

They call this Alpine enthusiast “The Tyrolean.” Vintage 1960s brown wool felt hat made exclusively for The Swiss Cheese Shop of Monroe Wisconsin. Black silky lining and silver pendant with horsehair florette on a dark brown headband. Current bid $45 on eBay.

Vintage Pendleton virgin wool trilby, made in Portland, Oregon. Buy It Now for $26.95 on eBay.

Take the Rat Pack to Palm Springs with the top down and this vintage 1960s light blue straw fedora with striped ribbon hat band, size large. Buy it Now for $26.91 on eBay, or make an offer.

Vintage 1960s Stevens beaver blend Homburg-style hat in original box. Size 6 3/4. $59.99 on eBay.

Vintage Dobbs Fifth Avenue New York stingy brim fedora, size 7. Buy It Now on eBay for $19.99.

Vintage 1960s Churchill fedora in original box. I want to rub myself all over this unbelievable red topper. Just look at that nautical rope band. The hat is a masterpiece. Size 6 7/8. $49.99 on eBay.