In an effort to gather all my writing in one place, I’ve begun to post articles that originally appeared elsewhere, or work that has been gathering dust on my hard drive. This piece was originally published by the The Morning News in 2002. Thanks to Rosecrans Baldwin, for the edits.

Flappers never had bad-hair days. They lopped off their tresses, tugged on a cloche, and headed out for an evening of Charleston and bootleg gin. What’s more, flappers wore comfy dresses shaped like potato sacks. They could wear whatever they liked; who the hell notices when you have that darling bell of a hat on? And so, you see, hats make life easier and loads more fun.

Unfortunately, hats have gotten a bad rap since they fell out of quotidian fashion in the late 1960s. Have you ever flirted from beneath the brim of a fedora, shaded your unblemished complexion from the summer sun with a straw hat, or sipped cappuccino thoughtfully in your beret? Of course not. All but a very few of us have abandoned hats to the crazy ladies.

Did I say crazy? Pardon me, I meant ‘eccentric.’ By eccentric I mean, ‘enamored of hot-glue guns and their ability to affix small, fake birds to felt.’ These are not the kinds of hats in which we’re interested. That is, unless you’re dressing as a Hitchcock movie for Halloween.

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Milliners will tell you that anyone can wear hats. They are lying.

Some women do not look well in hats, just as some should avoid turtlenecks or string bikinis. That said, many women believe they look terrible in hats, but in reality simply don’t know how to wear them. There are five ways you can dramatically increase your odds:

1. Find a color that complements your skin. Hats are closer to your face than anything else you wear. Hence, if the color isn’t flattering, it will be especially noticeable. I know it’s the sweetest hat you’ve ever seen, and it would look so great with your boots, and it matches your eyes, and so on. Try the hat in a natural light. If it makes you look sallow, put it back.

2. Wear your hair differently. Many women just plunk a hat on top of their everyday hairstyle. If you already have a wide face, this can exaggerate it to an unflattering effect, especially if you have long or full hair. If you really like a particular hat, but just don’t think it works on you, try pulling your hair back in a tight chignon or a low ponytail at the nape of your neck, or pinning the front sections back. At the very least, tuck hair behind your ears. It may improve matters dramatically.

3. Choose a hat that works with your face shape. If you have an oval or triangular face, you’re one lucky bird. You can wear almost any hat, and you can wear it as far forward or back as you please. You can also pick any kind of brim without looking like you’re wearing a life preserver on your head. The hat’s crown (the part that fits down over your head) shouldn’t be narrower than your cheekbones.

If you have a round or square face, wear your brims on an angle when possible. You’ll want the crown of the hat to be at least as wide as your face. Hats with a wide, high crown will work especially well.

If you have an oblong face, stay away from tall hats. Wide brims will counterbalance the vertical stretch. You might also try pulling the brim down to your eyebrows to shorten your face and to hide excess forehead.

4. Make sure the hat is angled to its best advantage. If a hat doesn’t look good when you first try it on, you may not be wearing it far enough forward or back. Many hats, especially stiffer hats made of felt or straw, will also wear better when you tilt them slightly. Try angling your hat to the right or left, and look at it from every direction in the mirror. It may look good from the front, but terrible from the side. Keep fussing until you find a position that works. If you can’t, assume that the hat is ugly and keep shopping.

5. Be sure you’re wearing the correct size. The average female head size is twenty-two and one half inches. If the hat comes down over your ears, or falls off easily, you’ll want a smaller size. If you fuss with your hat, or if it makes your forehead itch, go up a size or two.

Hat Quality
If you’re headed to Ascot this year, you’ll want something nice. A quality hat is relatively easy to distinguish.

Straw-hat making is a time-consuming endeavor, as they are almost entirely hand woven. Most of them are produced in China and the Philippines. Straw is braided, and then sewn into shape. The most prized straw hats are produced with a fine straw, in a small, tight weave. A hat of good-quality straw can take a weaver up to twenty-five hours to complete.

If you’re buying a felt hat, look for wool felt, peachbloom, or fur felt, which is made from rabbit fur. More expensive felt hats are often lined. Hat trim should be sewn on to the hat’s form, and not glued in place.

Many of the hats you see on the street are ‘factory hats.’ Mass-produced, and made of lower quality materials, these hats are practical and mostly casual. Designer hats are a step up. They often have limited production runs and are made of high-quality materials.

The haute couture of the hat world is called ‘model millinery.’ These extravagant hats are hand-sewn and pieced together using only the finest materials. They’re often made for a single customer who is attending a particular event, after which the design is retired.

Storage and Repair
Store more expensive hats in hat boxes to keep them from getting dusty or discoloring in the light. Line the box with tissue paper and place crumpled paper in the hat’s crown to help it hold its shape. You may want to overstuff the crown a bit so the brim of the hat lifts up from the bottom of the box. This way the paper supports the hat’s weight, and the brim doesn’t become distorted. Add enough paper to your box so that the hat will not move if the box is jostled.

Don’t wear hats in the rain, unless they are rain hats. Nothing damages a hat more quickly than water, except perhaps fire. Don’t wear hats in the event of a fire.

If you have a felt or straw hat that’s been dented, you may be able to repair it with steam. Put a full kettle on to boil and wait until it begins to steam consistently. Turn the heat down a bit, but be sure the steam still has a little force to it.

Place the dent over your steaming kettle and move your hat around until the steam penetrates evenly. (This should take about twenty to thirty seconds.) Remove the hat from the steam and use your fingers to push the dent out, and then blow on the affected area to cool it. Use caution when you’re working with steam in a small area: too much can exacerbate damage.

You can also make an old hat stiffer by steaming it thoroughly and letting it cool. This reactivates the stiffening agents milliners used to make the hat.

If all of this sounds too complex, or too burn inducing, most milliners will reblock your hat for a fee.

Hat Types
Hats are either brimmed or brimless and they take two forms—a hat or a cap. Milliners fancy up the basics with trims and detailing. A few types of hats and their preferred uses:

Alpine: Down-filled fabric hat with storm flaps for ears, neck, and forehead. Perfect for hunting wabbits or hiding winter hickeys.

Beret: Felt cap with wide circular crown. For coffee, commutes, scouting, miming, and youthful affairs with political leaders.

Chignon Cap: A piece of fabric that covers a bun. Ideal for naughty-French-maid Tuesdays.

Cloche: A ‘20s felt hat that resembles a bell. Useful for blocking unwelcome eye contact when you’re trying to read on the bus.

Cowboy Hat: Originally developed for cattle herders, it has evolved into a signal that you are attending a bachelorette party.

Derby (or Bowler): Domed crown with narrow brim that curls upward. Excellent for Charlie-Chaplin costumes.

Fedora: A men’s hat that has since been adapted for women’s wear. Brimmed, and made of felt with a lengthwise crease in the crown. Effective for modern-jazz-dance routines when worn with a men’s-style shirt unbuttoned indecently.

Newsboy Cap: Full fabric cap with visor. Great when paired with knickers for ironic rounds of golf at your local putt-putt course.

Stocking Cap: Knitted, with a long tail that often ends in a pompom. Good for midnight runs through town with a candle, or snowboarding in 1995.

Watch Cap: Knitted sailor cap that rolls down or up depending upon your warmth needs. Best stolen from a boyfriend just before you tell him you know about that girl.

Hats Off
Though a gentleman must remove his hat indoors, ladies can wear theirs wherever they like. However, don’t wear one in your own home when you’re hosting a party. Otherwise, it looks as though you’re about to head out someplace better.

Hats draw attention, so it takes confidence to wear one well. If you can manage it, other women will assume that you are more fashionable than they. Those women will be correct.