I suggest you start by putting an ad in the Classifieds right here.
Check out the ad I put up a couple of days ago for my Stetson Temple - you need a few decent pictures, a clear description of the hat's condition and any issues (sizing, quirks, damage). Make it clear how you want to be paid (PayPal or old-school mailed check/money order) and what the shipping charge is. For the Temple, I came up with a starting price by roughly dividing the current retail cost in half, and decided I could be a sport and pay the shipping, since I want to present a bargain.
Of course, I see I haven't gotten any bites yet! If that's still the case after a week, I will bump the topic and drop the price $5, and continue for a few weeks, until it becomes clear that there's really nobody interested. But I have sold both hats and jackets successfully through the Classifieds forum... and it's satisfying to know that these items are going to the good people of TFL!
I say it depends on the market you are catering to. The Good Doctor's advice is excellent, but as far as asking price, you are going to get different results if you sell here, in person (antique mall or thrift store), and on an auction site.
I think you are only going to get "top dollar" for certain hats, or types of hats, here on the FL. An old school Stetson, a Wormser, or a Dobbs in the right style (high crown, wide brim). The interest around here centers on classic vintage hats. In a thrift store or antique mall (assuming you had one, LOL), you will get a wider variety of interested parties. There, you can find folks who are more willing to buy newer models, stingy brims, and other things not so coveted by most lounge members. Price point here depends on foot traffic.
An auction site, such as eBay, is where you will get the most eyes on it and reach a larger pool of potential buyers, resulting in more competition and higher sale prices. Of course, there is more hassle with selling on the Bay. If you choose to go down the auction site road, look at how much similar hats have sold for recently, and price accordingly.
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