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Q: I really want a men’s carryall but I’m worried about being ridiculed for carrying a “man purse.” What are some chic yet masculine options?
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Rewind to…Preps!Also known as Paige, Ashley, Claire, Missy, Skip, Biff, Blane, Palmer, Carlton, Madison...

Jacket art for The Official Preppy Handbook.

Fashion Dos: Lacoste
or Polo Ralph Lauren shirts with upturned collars. Chinos with rolled cuffs. Sperry Top-Siders. Tasseled penny loafers. Duck boots. Après-ski. Mess­­ing with the townies. Cable-knit sweaters around the shoul­ders (around the waist if you’re dieting). Oxfords. Plaid Burberry skirts. Pat­terned Tretorns. Pink! Or kelly green. Spreading rumours about the new girl.

Fashion Don’ts: Shopping at the mall
Faux-low (e.g. Fox-brand polo shirts). Socks. The softer side of Sears. Black. Polyester. Public transit.

Patron Saints
James Spader in Pretty in Pink. Kim Walker in Heathers.

Natural Enemies
Nerds, punks, metal-heads, freaks, burn­outs, the pregnant girl, the socially underprivileged, BiWay shoppers.

To Monogram or Not to Monogram…
Only if your last name is followed by “III” or higher.

Career Aspirations
Rowing team, Wall Street, yuppie­hood. Or married to that.

Required Viewing
Making the Grade, Class, Less Than Zero.

The Bible
Lisa Birnbach’s The Official Preppy Hand­book (Workman Publishing Company, 1980). And the latest L.L.Bean catalogue.