I adore hats! My everyday winter hat is made of heavy-weight olive-green cotton flannel (scrap from a suit I made myself) and has a ruched crown and a broad snap-brim which I generally keep turned up, though I will pull the front down, Robin-Hood style when it is raining, to keep my glasses dry. I lined it with some paisley-printed green satin left over from a dress I made to wear to a friend's wedding. My favorite decorative/non-functional hat is the pleather biker hat I made for myself out of scrap from my pimpin' pleather trench coat (inspired by the coat SMG always wore as Buffy in "Buffy the Vampire Slayer") I'm wearing the hat in the picture I use as my avatar, though it is a little hard to see since the picture is so tiny. It has a little chain held down by two silver buttons across the front and it is lined in fuscia satin. I've got an old brown/grey tweed men's Stetson hat (like old men wear, not a cowboy hat) that I love to bits and pieces, and I may be getting a grey/black one pretty soon. Very gender bending. My other winter hat, that I don't wear so much because it doesn't cover my ears, is a red, velvet porkpie hat. I bought it because it was so pretty, but it isn't that practical, as it is not a snug fit so it blows off easily, it is too heavy for fall wear and as mentioned before, doesn't cover my ears. There is a reason I don't often make impulse purchases... For men, I love those flat caps (used to be stereotypical wear for Yorkshire men) but they can look really cute. They're akin to the Kangol hats that were so popular a couple of years ago. Fedoras are great, too--my husband has one and he looks so snazzy in it. If you're really cheeky and can wear a bowler without looking like a prat, my hat is off to you, and I may swoon in your general direction. Also, any really witty winter hat, like the ones that look like old aviator helmets or the liripipe style ones. Something about a man who is confident enough to wear a truly silly hat just warms the cockles of my heart.