If you’re looking to express your offbeat, kooky personality, dressing preppy probably isn’t for you. The number one principle is sameness. Sameness from day-to-day but also sameness with your fellow Preps. You have your sturdy go-to wardrobe staples – your beige corduroys for the weekend, your tennis whites, your navy blue suit, pink polo for picnics – and then you never need to think about wardrobe ever again.

Still intrigued? Here are some basic tenets to follow when dressing, courtesy of the Handbook:

1. Conservatism
2. Neatness – Yes, you do need to tuck in your shirt.
3. Attention to detail – skimp on the details and everyone will spot you for a fake!
4. Practicality – forget stiletto heels; embrace the classic pump
5. Quality – No, you don’t go to Forever 21 and load up on trendy clothes.
6. Natural Fibers – synthetics scream disco era, poor taste, lack of money.
7. Anglophilia – Except maybe for Burberrys, now that they’ve cheapened the brand.
8. Specific Color Blindness – pastels do go with primary colors!
9. The Sporting Look – even if you’d never hunt down a spider in your bathroom in order to flush it down the toilet, it’s best to look as if you’re joining a fox hunt in ten minutes. Or going off to flush pheasants from your hedges. But beware: the deer hunting look doesn’t pass muster.
10. Androgyny – your khakis, rain gear, wool sweaters and tweed jackets should look just as good on Muffy as they do on Bink.

And more guidelines, courtesy of the article, “Preppies: The Last Upper Class” by Nelson W. Aldrich Jr. in the Atlantic Monthly from January, 1979:

“Preppie clothing is so uniform that it betrays a group consciousness as distinct as that of investment bankers or arriviste Arabs. A list of articles in the Preppie wardrobe would be tedious, but the following are some of the more familiar items: LL Bean boots, Top-Sider moccasins, tasseled loafers; pure wool socks, black silk socks, no socks; baggy chinos, baggy brick-red or lime or yellow or pink or Pulitzer trousers, baggy Brooks Brothers trousers, baggy boxer underpants; shirts of blue, pink, yellow, or striped Oxford, sometimes buttoned down, some made for a collar pin, usually from Brooks or J. Press or The [name of town or college] Shop; jackets of tweed, corduroy, poplin, seersucker with padless shoulders, a loose fit around the waist, and (if tweed) a muddy pattern; a shapeless muddy-patterned tweed overcoat, its collar lopsidedly rolled up under one ear, a shapeless beige raincoat bleached by years of use and irresistant to rain; no hat, a cross country ski cap, a very old snap-brimmed felt hat, a very old tennis hat.

Thus the male preppie wardrobe.”

If that’s not enough help, here are some more ideas for men and women alike:

• Anything monogrammed.
• You can’t go wrong with a turtleneck. Not a turtleneck sweater but a straight-on, cotton turtleneck. Solids are fine, but if you can find one with a tiny repeating pattern of spouting whales, sailboats, tennis racquets or even fall leaves, you scored big-time. Pair a tucked-in turtleneck with some khakis and you’re golden. Don’t forget your leather boat shoes (Sperry Top-Siders)! Extra-credit: boat shoes, no socks. Very prep, very stinky.
• A cable-knit sweater with khakis or a skirt. Not jeans! Jeans just don’t figure into this at all, so get them out of your closet and your mind. Better: turtleneck, oxford shirt, cable-knit sweater paired with chinos. Prep-alicious! Extra-credit – roll or cuff the pants a few times to show off striped or argyle socks.
• Men should own plaid cotton button down shirts. Not flannel. Flannel is OK if you are up at the cottage helping Uncle Kip split wood on a fall Saturday. Otherwise, forget it. Women should have several plaid, wool skirts and/or trousers.
• Women should invest in a silk blouse that has a built in bow at the neck. They could also invest in a silk tie to wear with a blouse and v-neck, cable-knit sweater.
• Men should own a navy blue suit and white shirt. Supplement with shirts that have thin stripes and shirts of other solid, pastel colors.
• Of course, there’s always the polo shirt with an insignia on the left chest. Everyone wants theirs to be Ralph Lauren (the ULTIMATE in preppy wear) but don’t forget about the Lacoste alligator. Men – you know you have to have one in hot pink. There’s no getting around it.
• Men – consider wearing Bermuda-length shorts, boat shoes, no socks, polo shirt and sport coat

Where To Shop
The holy grail of the prep look is still LL Bean. Apparently, LL is even bring back its retired Norwegian pullover sweater (the Handbook refers to this sweater as “the nearest thing to a Prep membership card) this month; long a popular item for prepsters and ivy league students.  Of course, Brooks Brothers, Ralph Lauren or Talbots will never steer you wrong.  If you’re “faking it til you’re makin’ it,” you can shop at J.C. Penney  or Land’s End for some staple items. And there’s always shopping online. Try Cable Car Clothiers, Murray’s Toggery Shop or H. Stockton.

If you’re not afraid to embrace what I call New Prep, you could buy Tommy Hilfiger. The problem with some of the New Prep designers, and even Ralph Lauren, is their reliance on the logo/brand that appears on their clothing. True preps remove the tags, insignias, etc whenever possible.

I find that GAP and J. Crew have changed over their clothing lines to cater more to the “urban hipster bohemian” look now instead of being truly preppy. Their clothes are usually not timeless but very dated after one or two seasons. This same look is touted in the show Gossip Girl. Yes, it’s heavy on prep but much too Sexy Prep. Where are the turtlenecks?

Amazing Finds
If you can get your hands on these items, you’re living the lux Prep life.
Long kilt paired with velvet blazer.
Embroidered corduroys ( men or women)
Real madras shorts
Needlepoint eyeglass case
Vintage Fair Isle cardigan or pullover sweater
Seersucker suit
Nantucket Reds
Chesterfield coat in gray herringbone

And now some random inspiration…