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“Are you going to wear that?” my husband asked as I tried on the flowered hat I had just scored from an estate sale. “…Yes?” I wanted to be firm, but the words came out a bit uncertainly. I have worn all sorts of “unusual” vintage hats since this project began, though typically the most outlandish ones I didn’t choose myself but was given or otherwise acquired indirectly. This big flowered hat came from an estate sale lot that had four hats. Two of them really interested me (more about them in later posts). The other two…well, I’ll just say they weren’t really to my taste. This one seemed twice as big on my head as it had appeared in the online picture. I look at a lot of estate sales online, but rarely do they contain hats, and if they do, they are usually modern, made-in-China sun hats that do not interest me. But this estate had FIFTEEN lots of vintage hats. If only one had been available, I would have bid on it. But with this many to choose from, I had to be selective. After all, I would have to find a way to store all the hats I got. I finally decided to bid on two of the lots. These estate sale auctions are tricky for me. Often the goods are grouped into lots, but I only want some of the items in a given lot. And since I can’t examine the goods in person, I have to pore over the often limited pictures online. Now, if I were a dealer, it wouldn’t matter. I would be planning to make a profit on all the items. Even a hat that is strange or in poor condition will sell if priced right. But for me, if a hat isn't wearable or isn't of interest to me, I would prefer not to spend money on it. So when bidding on the two lots, I had to figure out, not what the whole grouping of hats was worth objectively, as a dealer would, but what they were worth to ME. Here is the first lot I decided to bid on: As you can see, any lot of hats is a mixed bag. That orange feathered hat, for example, is simply frightening--I'd feel like a Muppet in it. I don’t need a plain white felt boater, or a small rose whimsy. Upon closer examination, the blue feathered hat had some condition issues. (I have a hat of similar materials, in white, and I knew to look for signs that whatever the milliner used to affix and sculpt the feathers was discoloring, and sure enough, it was). So bidding on this lot came down to two hats: the brown-and-white, black-checked straw, and the white saucer hat. The straw hat seemed a little misshapen, and might require steaming to put to rights, but it was a very unusual hat, which attracted me. However the one I really wanted was the white saucer (or mushroom or platter) hat. I have a real fondness for that shape, which is emblematic of the fifties and early sixties (Dior introduced one in his famous New Look collection late in the 1940s, and the shape remained popular for more than a decade). I knew the hat would be valuable for a reseller—they could probably list it for the $50.00 range, depending on condition. If I just considered the two hats that interested me, together they could be worth maybe $80 plus, and the other hats would also be worth money to a reseller, making the whole lot worth even more. HOWEVER, the fact that the hat I really wanted was white made me hesitate to pay top dollar, as it could possibly have discolorations not shown in the photos. I put in a bid for around $40 (including buyer's premium). In these online estate auctions, bidders are prone to swooping in at the last second and jacking up the price, so you need to leave some headroom in your bid. I had theater tickets for when the bidding would be closing, so I couldn’t watch and counterbid. In this case, I put in my somewhat lowball offer and hoped for the best, as you can put in your top offer and the software will counter other bidders until they outbid your highest amount. Unfortunately for me, another hat collector or resaler was also bidding, and as my husband and I went to take our seats for the show, I saw that she had countered my bid. I was still on top, but she was only ten dollars away. So I had to decide whether to raise my bid or potentially let the lot go. I thought about, not what those five hats were worth objectively, but what they were worth to me, and decided not to go any higher. The second lot I bid on (which had this flowered had in it) was more enticing. The two hats that interested me were both beautiful and unusual. Right before the play started, I was in the same situation on the second lot. The other collector was also bidding, and I was still on top, but not by much. In the case of the second lot, I raised my bid. And then I silenced my cell phone. At intermission, I discovered that the other collector had indeed tried to outbid me near the auction close. In the case of the first lot, she succeeded, but I prevailed in the second lot. I was satisfied. That gave me four hats to play around with. BTW, whoever the second bidder was, she had very similar taste to me. She only bid on the three lots that had the oldest and most unique hats. She won two, but I got the third. When I picked up the hats, I noticed a slight musty smell. I decided to try spritzing with vodka to disinfect/deodorize the hats. I hadn’t done that with hats before, just clothes, so I started with the hat I thought would be easiest and I wouldn't be super upset about accidentally damaging, this flowered hat. The process was pain-free and gave me the chance to refluff the slightly crushed flowers. Even after cleaning, I put off wearing it. It is a little much. I don’t often feel self-conscious in a hat, but I did in this one, especially since the day I wore it I not only sang in front of the church, but read the lesson. No lurking in the back possible! I reminded myself of my motto to “wear every hat” and went forward. One of the hat stores I follow on Etsy posted a listing for a similar (if nicer) hat, calling it a “Midsummer hat.” I guess I wore this hat as more of an “Late Summer” hat. It WAS a little past season. When I turned up wearing it in church, people said things like “You look like you’re ready for Easter,” and “You look like you should be in a wedding.” I just smiled and decided that if the roses were still blooming in front of the church (where my husband took the pictures for this blog) I could wear a rose hat, even in October.
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AuthorAnn Hillesland writes fiction and nonfiction and collects hats. In this blog she vows to wear (not just model, but wear out of the house) every one of her hats, blogging about their histories and their meanings for her. Archives
October 2025
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