In an effort to gather all my writing in one place, every Monday I 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.

Welcome to the first installment of the Women’s Fashion Guide. In this ongoing series, we’ll help fill in your wardrobe gaps, forgive your past sins, and encourage you to shine your stilettos.

This week’s article is about classic clothing. Recall your mother’s timeless refrains: ‘That won’t match anything.’ ‘That will fall apart in the wash.’ ‘That dress makes you look like a hussy.’

Mom was right. That dress did make you look like a hussy. Fortunately, your high-school crush thought so too. But mom was also right about sensible shopping. You could use a new pantsuit.

Building a Wardrobe

Thank god you were born a woman.

The sartorially adventurous man can have a red shirt made, perhaps purchase a loud tie. You, on the other hand, can pour yourself into a crimson dress with built-in panties and fish-scale sequins that chatter as you walk. You can halt conversation; you can smirk as gentlemen loosen their ties and swallow hard; you need never pay for a drink.

Wear what you want. Dive into feathery chiffon swing skirts, witty little gemstone bracelets, kissable cashmere wraps. Roll around in the delicate, glittering, unctuous glory of it all!

All right, now get up off the floor. You’re crushing your feather boa. Also, your closet is starting to look like the wardrobe rack for Moulin Rouge. Is it, or is it not true that you own seven brand-new miniskirts, but not a single pair of shoes that matches your interview suit? I thought so.

If you want to build a wardrobe, you have to start with the basics, clothes you can count on. Once you have some solid building blocks in neutral colors, buy the silly, sparkly separates and accessories that will keep your girlfriends from yawning. For now, we’ll focus on tried and true.

White Button-Down Shirt
If you’re a tall girl and you’re dating a skinny guy with a good tailor, you may be able to score one of these by batting your eyes and slipping it on. If you’re 5’3″ and your boyfriend is a linebacker, head to your favorite boutique and look for a crisp, white shirt made of 100 percent cotton.

Find one with darts that bring the waist in slightly. You need a shirt that looks good untucked: i.e., that doesn’t come more than halfway down your bum and isn’t too baggy—but can also be tucked in for wear with a suit.

Details will date the shirt, so find something that doesn’t have peasant ties at the wrists or prissy little flowers embroidered on the collar. Avoid shirts with breast pockets, that way you don’t have to worry about whether your bust line makes the pocket gape. The right piece will look as good with a business suit as it does with your white cotton undies. Press it until it crackles. Wear it with a pencil skirt for business or a plaid pleated skirt for pleasure.

Knee-Length A-Line Skirt
These look good on every shape and can be dressed up or down. Buy a skirt in a solid, neutral color and a fabric that will work in any season, like a lightweight wool gabardine.

Try a striped T-shirt, matching cardigan, and flats for breakfast with a girlfriend. Pair a black skirt with heels and something low cut for dinner.

T-Shirts
You’ll need one black, gray, or navy T-shirt and one in either white or cream, depending on your complexion. Look for a cotton/polyester blend: It will fit your curves better than a purely cotton version, it won’t look tired so quickly, and it will travel well. Find a thick, durable weave. Thin T-shirts wrinkle easily, and they also show every bump of lace on your bra.

When you find the right T-shirt, go back and buy two more in your favorite bright colors. They’re perfect for layering under a bulky sweater in the winter or for pairing with a pair of tidy, side-zip shorts when you’re out sailing. OK, washing the car.

Jeans
Pull them on; glance in the mirror. If your ass doesn’t look antigravitational in these jeans, if it doesn’t look like some other woman’s ass entirely, put them back. They should also break just-so over your sneakers. If you’re petite, consider having them hemmed by a tailor who knows that jeans should never, ever look like they’ve been hemmed.

Shop until you find the best possible pair. Can you heft moving boxes without displaying a porn-star triangle of G-string? Could you picnic with his parents in these jeans? Could you successfully accessorize with a tank top and a shot of tequila?

When you find the right pair, don’t agonize over the price tag. No matter how much you spend on them, it’ll still work out to about five cents a wearing. So buy the pair you want. Buy two.

Warm Sweater
If cream looks good on you, find a chunky turtleneck sweater in off-white. It goes with everything, and looks equally charming with a pair of jeans or with a skirt and boots. If cream makes you look warmed over, consider camel, chocolate, or black.

If you feel like something dead is wrapped around your throat when you wear a turtleneck, or if your neck is so short that you sometimes have trouble turning your head, opt for a very slight V-neck.

Slim Casual Pants
Think Jackie Kennedy, not Army/Navy. No pleats, no bottom cuffs, no cargo pockets, no kicky little waist ties. No. Find a pair with a flat front, one button, and one zipper. Go with a slightly tapered or straight leg.

You can wear them with anything, but keep them pressed. Pull them on when you’re running for bagels in the morning. For a well-scrubbed look, pair with bright, fitted V-neck sweaters, or a T-shirt and a front-zip, hooded sweatshirt.

Knee-High Leather Boots
Some women take to these, other women feel like hookers. Nothing is sexier or classier with a skirt. If anyone propositions you, your skirt is too short.

Trench Coat
Buy yourself a black or khaki trench coat and you’ll wear it everywhere but the opera. It looks great with jeans and winter skirts, and adding a colorful scarf will pull most looks together with minimal effort.

Find a coat that’s fully lined and impeccably tailored. If you can’t afford a new coat—and they can be expensive—you can usually find them at vintage boutiques. Vintage varieties have luxuriously deep pockets that let you shove your hands in up to your elbows. This is a rare and wondrous element in women’s clothing, so seek it out.

Dark Pant Suit
Why are most women’s suits a little Miami Vice? It’s a hundred times easier to find an affordable and flattering suit in lavender or sage than in black. But it’s worth the extra cost to own a suit that doesn’t make you look like an after-dinner mint.

Look for a single-breasted pantsuit with classic lines and trousers that you can wear separately. Search out light, seasonless fabrics like crêpe. Avoid odd, trendy buttons and synthetic fabrics. The pants should break over the shoes you’ll be wearing (heels or flats: choose before you buy) and the sleeves shouldn’t be too long or too short.

Little Black Dress
Cigarette holders have gone out of vogue, but as long as you can still order a good martini, you’ll need a little black dress.

Avoid ruffles, lace, multiple fabric combinations, and asymmetrical tailoring (a toga top, or a skirt with an uneven hem). The perfect dress should be comfortable, well fitted, and just the right length to hit the most flattering point on your let. Too-tight dresses sacrifice elegance. You’ll most likely be wearing shoes that hurt: do you really want to suck your gut in all night, too? Find something with both elegance and sex appeal.

In the dressing room, ask yourself a few questions. Do you feel calm? Slightly superior? Could you wear back-seam stockings without looking trashy? Could you make eye contact with a charming gentleman across the room, part your lips, and raise your eyebrows ever so slightly? If so, wrap it up.

What’s Left Unsaid
If you have to try on dozens of outfits to find one that looks handsome but still casual, you don’t own enough classic pieces. The above list is by no means complete. We haven’t even touched on wool pants, minimalist leather jackets, black heels that you can dance in, cashmere cardigans, and the multitude of accessories you should have in your arsenal.

Too many women waste too much time trying to look as though they’ve just thrown something on. With these pieces, you’ll actually be able to choose an outfit at one go, which gives you more time to decide which lipstick to wear.