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.

Obi Belt

Does anyone else suck at wearing belts?

ASOS Square Buckle Skinny Boyfriend Belt

I must be missing the gene, because every time I try to add a belt to my outfit, it only seems to make things worse.

Super Wide Elastic Belt

Belt mastery is the highest form of fashion-fu.

This is every item of clothing I packed for five days in Jamaica. I love packing for warm weather because it’s so easy to shove everything in a carryon.

For once, I took a photo of my travel outfit. In this photo, it’s 5 a.m. in chilly San Francisco. My formula for the perfect travel outfit is always:

comfy knit dress (ISDA and Co.) + leggings (H&M) + scarf (gift from Vietnam) + cardigan (H&M) + slip on shoes (H&M)

The scarf doubles as a wrap, and on the way home I wore the same outfit with an American Apparel circle scarf, which is magical and also works as a sarong or a shawl.

When I arrived for my four-hour layover in Miami, I was able to shed down to this, so I wasn’t sweating when I got to Jamaica. Jamaica!

I changed into sandals upon arrival and wore this to dinner on the beach.

The next morning, our first activity was a press tour of the Secrets Resort where we were staying. My striped shirt is H&M, the shorts are Rocawear (Shut up. I’m squarely in their brand demographic. Also! Those are on sale for $8 now. Go buy some so we can be twins). This outfit is my confused attempt at businessy tropical. Sort of. It turns out I didn’t need to worry much about the business part:

These shorts are stretchy. I’m pretty sure I wasn’t supposed to be on this trampoline, but I hung back until the tour guide had turned away, and bam. Actionwear!

After the Secrets tour, the Jamaican Tourist Board rounded us up on a bus to take us dogsledding and waterfall climbing (more on that later). My navy shirt and shorts are both American Apparel.

This JCrew fedora is pretty much the best hat ever. I bought it in XL so it would look like I borrowed it from a cute boy. Then Bryan tried to wear it out of the store, and I had to assert.

This is me and JoAnna conquering Dunns River Falls. Apparently I now flex whenever a camera is turned my way. My bikini is American Apparel, and it covers stretch marks with aplomb.

Secrets has a dress code for dinner, so I changed into this American Apparel minidress. Actually, I think technically it’s a T-shirt. It’s nearly impossible to wear something in a way that’s sluttier than American Apparel intends, but I got it done y’all. The earrings are from Claires.

The dress is daring, but even more so because of the low back. I paired it with American Apparel shorts so I only appeared to be on the verge of exposure.

See? This is the same look dressed down a bit. These black shorts are identical to the navy pair I’m wearing above, by the way. Here the dress reads more like the shirt it actually is.

My Southwestern sandals are BC from Zappos, which is a lifesaver when you have two days to find shoes for your trip.

As you know, I always try to pack PJs that double as outfits in case something comes up. I wore this Old Navy tee and H&M shorts to bed, and also to hang by the pool.

This romper was $9.80 at Forever 21. Are you proud of me for ignoring my impulse to iron it while on a tropical island? Thanks.

I wore this as a coverup, and I’m kind of amazed that it hasn’t fallen apart yet. Of course if I don’t hand wash it, the thing will probably shrink up to swimsuit size, but has pockets, so I threw caution to the wind.

My excellent yellow turban is from a gift shop in Puerto Rico. I got it on the same shopping trip when I failed to convince Melissa to buy the stripper heels with the zipper up the back.

I didn’t have a good pair of ruinable flip-flops, so I got these at Gap right before I left. I’m a big fan of metallic shoes for travel because they work with everything. These withstood the beach way better than I expected.

You’ve seen this DKNY suit before. The outer skirt pulls down to miniskirt length or pushes up to your midsection. You’ll be glad to note that I didn’t wear this to dinner as a dress.

This is a vintage silk Vera scarf, which is my go-to wet hair solution. Pro-tip: If you have trouble with scarves slipping off your head, you’re probably buying polyester instead of silk. Fortunately, you can find silk scarves pretty cheap second hand. This one was $5.

This is what I wore for our tour of Rose Hall. I got this candy-striper stripe top at H&M. I wore it over a romper, but also as a coverup with my bikini.

I’ve had these Saltwater Sandals for years. They’re literally made for walking on the beach.

This is my favorite photo from the trip, taken by the very patient and talented Kate. (Holy, holy go check out the World Cup commercial she filmed for Puma. Goosebumps.)

The playsuit is by Cotton + Candy, which doesn’t seem to be an Internet-friendly brand. If you live in the city, I got it on the Haight at X-Generation, and it is my new favorite thing.

And, aside from my underwear (five pairs, two bras — one strapless), and a black drapey dress I wore in Greece, that’s my trip in a carry on.

This little red dress is one of those outfits guaranteed to make you feel happy. I got it at H&M for ten bucks. When saw the price tag, I think I may have howled at the sky in triumph. It’s poly-so it packs like a dream, even with all the ruffles.

In the morning I set out on a long walk in my sneakers and dress. It turns out the men of New York are very verbal about their appreciation for red dresses. My favorite exchange:

-That’s a real pretty red dress.
-Thanks.
-You gotta get yourself some nice stilettos to go with it though.
-Why don’t you get some stilettos to go with yours?
-…Bitch.
-Uh-huh.

The jacket is also H&M, my shoes are Puma. It was sunny and warm when I started out, and pouring by the time I arrived. I bought this umbrella along the way.

Here’s a blurry close-up of the shoes. I wasn’t sober when I took it, and I had just spilled bourbon on them. Sorry, shoes.

I wore this into Brooklyn for drinks, and it was also my traveling outfit for the next day. The shirt is Old Navy, the Jeans are Express, and my scarf is vintage.

The only thing I packed that I didn’t need on this trip was a cotton robe to use on treks to the communal bathroom at the Jane Hotel (they had robes in the room). I wore a cotton knit sundress to bed, in keeping with my philosophy of packing double-duty jammies in case I need an extra outfit.

Turns out it’s way, way easier to pack for New York in Spring than in Winter. I can’t wait for summer trips when you can take three weeks worth of clothing in a carryon.

Hey Laura, let’s take a moment to pause in the scenic parking lot outside our hotel at 2 a.m. because I forgot to take a picture of my outfit today.

Excellent. The jacket is thrifted, the purse is vintage, the expression is happy exhaustion. In real life, the blues are a little more harmonious than they appear under the parking lot spotlights.

This dress is a new favorite. I just picked it up at a vintage shop, and it fit like this right off the rack. Bam! it also rolls up into a little ball for packing and doesn’t wrinkle. Pow! Sock! Tights are from Target, and the little thing on my shoulder is a Fitbit. It’s like a pedometer that makes out with the Internet.

My shoes are also Target, and the pink purse has snaps on the side that let you make it clutch-sized, or larger like I have it here. My bracelet is from a museum shop in Buenos Aires, and so I especially enjoy it when people ask me where I got it.