The Official Preppy Handbook

Fashion Rules

We know that many of you understand the principles of preppy style. But just to be sure, let’s review them again.

We wear sportswear. This makes it easier to go from sporting events to social events (not that there is much difference) without changing.

We generally underdress. We prefer it to overdressing.

Your underwear must not show. Wear a nude-colored strapless bra. Pull up your pants. Wear a belt. Do something. Use a tie!

We do not display our wit through T-shirt slogans.

Every single one of us—no matter the age or gender or sexual preference—owns a blue blazer.

We take care of our clothes, but we’re not obsessive. A tiny hole in a sweater, a teensy stain on the knee of our trousers, doesn’t throw us. (We are the people who brought you duct-taped Blucher moccasins.)

We do, however, wear a lot of white in the summer, and it must be spotless.

Don’t knock seersucker till you’ve tried it. (Between Memorial Day and Labor Day, unless you live in Palm Beach or Southern California, or the southern Mediterranean, please.)

Bags and shoes need not match.

Jewelry should not match, though metals should.

On the other hand, your watch doesn’t have to be the same metal as your jewelry.

And you can wear gold with a platinum wedding band and/or engagement ring.

Men’s jewelry should be restricted to a handsome watch, a wedding band if he is American and married, and nothing else. If he has a family-crest ring, it may be worn as well. For black-tie, of course, shirt studs and matching cuff links are de rigueur.

Nose rings are never preppy.

Neither (shudder) are belly-button piercings.

Nor are (two shudders) tongue studs.

And that goes for ankle bracelets.

Tattoos: Men who have been in a war have them, and that’s one thing. (Gang wars don’t count.) Anyone else looks like she is trying hard to be cool. Since the body ages, if you must tattoo, find a spot that won’t stretch too much. One day you will want to wear a halter-necked backless gown. Will you want everyone at the party to know you once loved John Krasinski?

Sneakers (a.k.a. tennis shoes, running shoes, trainers) are not worn with skirts.

Men may wear sneakers with linen or cotton trousers to casual summer parties.

Women over the age of 15 may wear a simple black dress. Women over the age of 21 must have several in rotation.

High-heel rule: You must be able to run in them—on cobblestones, on a dock, in case of a spontaneous foot race.

Clothes can cost any amount, but they must fit. Many a preppy has an item from a vintage shop or a lost-and-found bin at the club that was tailored and looks incredibly chic.

Do not fret if cashmere is too pricey. Preppies love cotton and merino-wool sweaters.

We do not wear our cell phones or BlackBerrys suspended from our belts. (That includes you, President Obama.)

Real suspenders are attached with buttons. We do not wear the clip versions.

Learn how to tie your bow tie. Do not invest in clip-ons.

Preppies are considerate about dressing our age. It is for you, not for us.

Men, if you made the mistake of buying Tevas or leather sandals, please give them to Goodwill.

You may, however, wear flip-flops to the beach if your toes are presentable. Be vigilant!

Pareos (sarongs) are for the beach, not for the mall. (Even if it’s near the beach.)

Riding boots may be worn by non-riders; cowboy boots may be worn by those who have never been on a horse. However, cowboy hats may not be worn by anyone who isn’t technically a cowboy or a cowgirl.

You may wear a Harvard sweatshirt if: you attended Harvard, your spouse attended Harvard, or your children attend Harvard. Otherwise, you are inviting an uncomfortable question.

If your best friend is a designer (clothes, accessories, jewelry), you should wear a piece from his or her collection. If his or her taste and yours don’t coincide, buy a piece or two to show your loyal support—but don’t wear them.

Every preppy woman has a friend who is a jewelry designer.

No man bags.

Preppies don’t perm their hair.

Preppy men do not believe that comb-overs disguise anything.

You can never go wrong with a trench coat.

Sweat suits are for sweating. You can try to get away with wearing sweats to carpool, to pick up the newspaper, or to drive to the dump, but last time you were at the dump, the drop-dead-attractive widower from Maple Lane was there, too.

And finally:

The best fashion statement is no fashion statement. – Vanity Fair.Com

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