In the comments on Monday’s post, Victoria asked something that has me perplexed:

Question: I used to work in at an investment banking firm. One female analyst was wearing clothes that were either grossly mismatched, or just too “loud”. She would wear super high heels or flashy shoes (not flip flops) and skirts would be a touch too short. I was approached a managing director about this analyst. She wanted to know how to broach this subject with this analyst. I had no idea what to say because frankly it was her style - she simply didn’t know how to dress any differently and technically, she was within the firm’s dress code guidelines. She was wearing proper shoes and suits. How do you approach somebody about their dressing style without offending them or sounding harsh and at the same time getting your point across???

I have been mulling this for days, and I still don’t know what the answer is. I know what the analyst was doing wrong–her wardrobe of too high heels and too short skirts was completely unprofessional–but I am at a loss as to how Victoria, or the manager, could or should have discussed this with the employee.

As much as we might hate the idea that appearance matters, in a professional setting appearance matters. Managers and clients will make snap judgments about your abilities based on how you present yourself, and you will do the same with co-workers and employees. In order to be a successful professional, you really do need to LOOK like a successful professional.

However, that does NOT mean you have to wear a Uniform to work every day. It is important that you know and follow the conventions for your office or profession, though; if you work in a more conservative field, for example, then graphic tees or jeans or peep toed shoes may not be acceptable, even on Casual Friday. Part of your responsibility is to know the conventions and follow them.

Following the conventions does NOT mean sacrificing personality, though. You can do a lot with color and texture and accessories; a basic black suit is less basic when you pair it with a really fabulous red bag or when you wrap yourself in a bright blue scarf. Following the rules does not exclude expressing your personal style, but it is important to find a balance. Think of it this way: on the weekends, you might have a beer in the afternoon and think nothing of it. But at the office I suspect you would be more likely to reach for a soda at three pm, because drinking at work is discouraged. So too with what you wear. It’s all about making choices.

But that still doesn’t answer the question of how to talk to the analyst about her choices, and here is where I will defer to the wisdom of the Internet. What would you say to this woman? How would you approach her? WOULD you approach her? Is there a way to tell her that her clothes are impacting her job performance?

Help me out here.

Don’t forget about The Working Closet’s Flickr pool–show us what you’re wearing to work! Come on, you know you want to.