What Not to Wear, Chicago Bar Style

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We're getting a lot of questions from readers about this article at Above the Law. For example, from one reader:

I am a 2L at law school and about to start as a summer associate at a law firm in Washington, D.C. There was an article on Above the Law about an event in Chicago on Fashion Do's and Don'ts. After reading this, I have absolutely no idea what is ok to wear. It seems like every professional clothing item I own now needs to be thrown out. I was just curious about your thoughts on this….is this the reality of what to wear in a law firm? Thanks so much!

We didn't attend the event, obviously, but we do have a few thoughts on some of the “rules” that they cite.

• Their General “Rule” Espoused:  Do not look sexy.
• Our “Rule”:  Do not dress in a way that makes people think you are looking for a husband or a date at the office.
• The Caveats:  However — this does not mean that you cannot wear heels, wear fitted clothing, or wear makeup. It does mean that you might want to rethink your life if your Saturday night makeup is the same as your Monday morning makeup, or if one top can do double duty for both of those situations. As we've mentioned before, heels that are too high should perhaps be avoided at the office. (We would say that the absolute, maximum borderline is 3.5″ or 4″ — keep in mind that most of our office shoes are more like 2″.)  You may want to leave your push-up bra at home.

• The “Rule”:  Always wear pantyhose.
• Our “Rule”: If it is your first week to a new job or professional situation, or if it's your first time meeting a new client or appearing before that judge, then wear hose.
• The Caveats:  Whether or not you have to keep wearing hose is a case-by-case determination. When you are attempting to determine whether you need to keep wearing hose, look to the older women there, not your fellow newbies or the people only slightly more superior than you. If you haven't seen someone else go bare-legged, then keep wearing hose or risk running afoul of that office's culture.
• Other applications:  Open-toe shoes, peep toe shoes, boots, sleeveless dresses, colored nail polish (and certainly dark nail polish)

• The “Rule”:  Do not wear red pumps, ever.
• Our “Rule”:  We have red pumps, and red flats (patent, no less). We would never wear them on an interview, but we might wear them to the office with a regular skirt. Factors to keep in mind:  Red high heels should not also be shiny — a very matte leather is what you want. Color matters:  A darker red can seem downright conservative. Furthermore, be wary of what kind of shoes they are — for example, if the shoes  already have a vintage sexy-secretary vibe to them, buy them in a matte black, not a red.
• The Caveats:  Know your office.

• The “Rule”:  Do not wear a ponytail, and for God's sake don't wear a side ponytail.
• Our “Rule”:  Meh. We're not really sure we have a rule here, aside from this:  Pigtails are never going to be a professional look.
• The Caveats:  We've talked before about whether a high ponytail can look professional, or whether one can wear a ponytail too often to the office, or what kinds of hair accessories you can wear. It varies based on your hair style, your office culture, and how neatly you look when your hair is back. In general, this author's personal rule is that I try to wear my hair down during the day (or at least when walking the halls or going to a meeting) but then pull it back when it's later in the evening or when I'm alone in the office working — but then that's primarily based on the reason that I don't generally look good in a ponytail.

Other things, we somewhat agree with — do not wear clothing that shows your lower-back tattoo; do not wear clothing that tells people something about your underwear. We would also caution that just because one judge says pants suits are fine for him does not mean that he is speaking for the entire judiciary — we've heard from at least one reader who notes that a local judge has openly expressed his preference for skirt suits. Readers, what are your thoughts on the “rules” as we've pulled them out? Any other thoughts on the “advice” from the event?