Adam Glassman
Photo: Robert Trachtenberg
Q: I just don't know how to dress for work anymore. I see colleagues wearing ripped jeans, low-cut tops, flip-flops...how do I tell if I'm crossing the line?

A: Anyone who thinks it's okay to flaunt her body 24/7 is, to put it mildly, confused—understandably, since the workplace dress code is so ambiguous now. It's pretty hard to mess up a suit; it's really easy to make mistakes when casual Fridays have leaked into the rest of the week. Plus, celebrities are setting unreasonable standards. But listen, ladies, they go to premieres, not offices.

American women desperately need workable guidelines. To develop yours, build a fashion database. Assess the nature of your profession. Observe what your boss wears—and your boss's boss—for clues to get-ahead style. Before an interview, research a prospective employer's corporate environment.

"What a woman wears in a business setting can be construed as an indicator of her judgment," says Scherri Roberts, vice president and director of human resources for my own company, Hearst Magazines—and she should know. Although the right clothes won't get you hired or promoted, the wrong ones can sure get in your way.

How to Look Like You Mean Business

Find the uniform for you. I used to be horrified by prep schools where everyone was dressed the same, but now I think it's invaluable to be able to turn to something that always looks smart, chic, and pulled together. It can be classic, like a suit with a knee-length skirt (no shorter—work-appropriate also means age- and body-appropriate). Wear it with a modest V-neck shell or a camisole with lace; just don't overdo the froufrou. A dress and jacket, while still authoritative, is softer. But you don't want beach clothes—like a sundress—washing over into work, and sheers are acceptable only if layered over a matching camisole or slip. Separates can look a bit offhand, however, unless everything is impeccable: pressed, stain-free, and finished with smart accessories like scarves, belts, discreet jewelry (flashy pieces are distracting), or sandals (not thongs) in a fun color.

The Never-Ever-at-Work List 

  • Flip-flops
  • Halter or tube tops
  • Anything strapless
  • Sweatpants
  • Deep cleavage
  • Shirts that cap between buttons
  • Anything soiled or wrinkled
  • Nightclub makeup
  • Evening hair with that unkept, "bedroom" look
  • Strong perfume
  • Sheer dresses and tops without proper lingerie
  • Microminis
  • Beat-up "weekend" jeans
  • Chipped nails
  • Belly shirts and navel-exposing pants
  • Short-shorts
  • Dirty old running shoes
  • Open-toed, high-heeled, strappy, shiny evening shoes