Net Worth

How do you wear a dramatic hat without screwing up your hairstyle? Get a fascinator hat, ideal for special occasions like weddings, funerals, and every formal event between the two. Popular in Europe, I'm quite sure you've seen them on the heads of British royals or as famously worn by the late Isabella Blow. Accessorize with red lipstick, arched brows, and the smokiest come hither look you can muster. (£50/$99)

Cloche Encounters

First popularized in the 1920s, the cloche hat was designed for women with short-cropped hair. Flappers showed off that lovely expanse of skin stretching from nape to collar, yet retained that certain air of mystery with the brim pulled down low. French for "bell," the sleek and close-fitting shape is a fashion classic — this updated fur felt version has a removable flower pin. Oh la la! ($255)

Rabbit Hunting

Up to 40% of body heat is lost through the head, therefore heavy duty gear, like this man's plaid wool and shearling Anchorage hat, is necessary for the most cold and windy snow days. Equal parts Elmer Fudd, Fargo, and punk rock, the black and red plaid check and oversized fit are the main attractions. Made by your grandpa's company, Woolrich, prospecting outfitters since the days of log cabins and such. ($45)

Thinking Cap

Protect your dome this winter with warm and cozy headgear like this bobble stitch knit cap. Knit from wool with a smidge of angora for that soft fuzzy halo affect and finished with a tiny bobble nub at the top and ribbing around the perimeter. Wear like a beret, tilted at an angle, and while you're at it get a few more in one of the 6 other colors because you'll love the fit. Makes a great holiday gift as well. ($28)

Checkmate

While you're out shopping for chilly weather gear, get yourself a smart chapeau like this tweed trilby hat. A deeply indented crown and short brim effectively feminize the traditional man's fedora. A popular British hat shape since the late 1890's, the large tweed check has been twisted into an interlocking star pattern for a modern take on an old classic. (£22/$45)

Flower Power

Flower petal swim caps first became popular during the 1960s. Remember those old saccharine sweet Doris Day movies? She always wore a modest one piece bathing suit and flower bomb swim cap just like this one to protect her dye job. Women with relaxed hair may also be reluctant to enter a pool without protection for an expensive hair do. Keep your locks dry with a guaranteed hit at the pool party; also available in white, blue or rainbow-coloured. ($53)

Zora Neale Hurston

Not a lot of people know this, but Zora Neale Hurston was a hat lady. I don't have any hard evidence, but in nearly every photograph I've seen, she's wearing a hat. Usually tilted to the side, sheilding her face. These people are rare, I don't know any at all — the hat people. I've recently enjoyed the pleasures and attentions of wearing a hat, but better than shoes? Better than chocolate?

Hat Check

"I realized early on in my career as a milliner that most women had lost the art of wearing a hat with confidence." - Louise Green
The above quote is so very true. When do you ever see women wearing real hats? How many hats do you own? Definitely more popular in the South, especially amongst the Sunday set — church ladies own atleast six! All of the hats at Louise Green Millinery are handmade, like this funky fresh straw English rider. ($162)

Leopard Lady Love

Retro style is my absolute favorite, and this leopard beret represents the 40s era to a T! Modeled by modern pin-up Bernie Dexter, this is the head gear for any girl who has ever been described as "sassy." Get your inner Marilyn on by accessorizing with a slinky top and wiggle skirt. When I get dressed I usually begin with shoes, but in this case I'm building my outfit around the hat. Handcrafted in British Columbia, this faux fur beret is a definite must have! ($110)

Jamacian Mafia Hat

I recently bought a similar hat at a Memorial Day street fair and whilst wearing said hat this week I was complimented by a stranger who stated that it looked like a Jamacian mafia hat...
No. 1, who knew there was a Jamacian mafia? And no. 2, I now feel cool as hell (lawd a mercy)! If you don't have a straw hat to rock this summer, then this one should definitely be on your shopping short-list. Called the Hourglass ($160) from Cha-Cha's House of ill Repute, check out the leopard trim on the brim and the embroidered spider on the crown. Irie mon!

Roman Holiday

Sexy Italian men on their Vespa scooters racing about Rome at madcap speeds whistling at the girls and wearing this hopsack cap by TracyWatts. ($160) But this version is for women and methinks I would look quite fetching in it. Would Ms. Audrey Hepburn have this chapeau in her collection? You betta believe it!