Does My Lipstick Make You Uncomfortable? Tough.

Red Lipstick On A Blonde Woman

As recent college graduates, my three female roommates and I are all working our first full-time “Big Girl” jobs. This includes working and mingling with both male and female coworkers of various generations, cultures, and ethnicities. This is much different from part-time jobs we held in college, where we mostly worked with our Gen-Y peers in retail, restaurant, or campus jobs. We are also experimenting with balancing our business-casual wardrobe with the desire to express our unique selves. Back in the summer, my roommates and I discussed our mutual concern regarding this balance, and specifically, the introduction of lipstick into our work ensemble.

Most of my friends and I love to wear lipstick. We are not afraid to rock a bold purple or hot pink on a fun night out or a casual day at the museums. Still, it was astonishing to me that we all had the same concern that on the first day we wore lipstick to work, even in a casual and ‘professional’ color, we knew we would likely be subject to comments, judgments, and stares from our coworkers and bosses. If we were lucky, we thought, these comments might die out after the first few times wearing it, as they learned that it was not a special-occasion thing, but something we wear casually.


The first day I wore lipstick to work I chose a professional, classic red paired with very minimal eye-makeup. Inevitably, when my boss greeted me in the morning, he did a double-take and said “Oh wow! Your face!” Later that day, someone asked me what the special occasion was. I expected these reactions. Still, I was frustrated and a little embarrassed.

I do not wear lipstick for anyone’s sake other than my own. I have found that many women feel confident or powerful when they wear lipstick, or they wear it because it matches their outfit. Despite the reason, so many people (often men, in my experience) seem to feel uncomfortable with this change in their environment and therefore compelled to comment on it.  A woman should be able to wear lipstick and not worry about the remarks, be it a compliment, general acknowledgement, or worse, an unpleasant judgment. It is certainly no man or woman’s place to squash the feelings of confidence in a woman by drawing (often negative) attention to her for wearing lipstick simply out of their own unease.

I am not sure why there are uncomfortable feelings or awkwardness surrounding a woman wearing lipstick, but I cannot help but think and fear that they come from an insecurity of being around a woman who feels powerful and/or confident in herself. I also think that by judging, (i.e. assuming it must be a special occasion) the commentators are trying make sense of it and pinpoint a reason for wearing it. They don’t consider the possibility that it might just make that woman feel good.

Like any trend, the history of lipstick’s popularity has prospered and waned. The earliest archaeological evidence for lipstick comes from about 3,000 BC in the Mesopotamia. Lipstick has at times represented power, used by both Cleopatra and Queen Elizabeth I. It was condemned by the Catholic Church and at times only considered appropriate for prostitutes who occupied the lower classes. In 1770, British Parliament passed a law suggesting that women who wore make up were witches who lured men into marriage.

The Industrial Revolution helped to revive lipstick through commercial means—ease of manufacturing, low prices, and photography. In the last century, the Hollywood effect has had a huge impact as notable icons from Marilyn Monroe and Elizabeth Taylor to Taylor Swift and Sandra Bullock have rocked the red lips. Today, it is considered classic and women of all ages, class, and careers continue to rock the trend in every color imaginable.

Regardless of its history, and as much as I wish I could assert myself a witch or queen, I want to remind you: a woman’s feeling of power or confidence does not impede on any other man or woman’s power or confidence. There is enough to go around and that fear is no reason to project discomfort onto a bold-lipped lady.

Let me be clear; I am not implying that all compliments are offensive or that they will be taken out of context. A sincere compliment is much appreciated, but most often, women do not wear lipstick because they want or need the compliment. They do it for themselves.

By now you may be confused as to how to behave around a lady wearing lipstick. I am here to relieve you of that pressure with three basic guidelines. I am sure this will help even if you have known a lady for 10 years and it is the first time you have ever seen makeup on her face. (Note: these should apply to any bold fashion or makeup choices on anyone.)

  1. Remember: this person is most likely not wearing lipstick to appease you, upset you, or seduce you.
  2. If you do not have anything nice to say, do not say anything at all. (Seriously, how hard is this to learn? It applies to all aspects of life.)
  3. If you really love the way the lipstick looks and must comment, keep it simple. “You look very nice today,” should work just fine. You do not need to single out a specific component of her appearance; she will get the message.

*BONUS: Know that when a woman wears lipstick, she is fierce and not to be messed with.


Annaliese Stockmeier : 90’s Rom-Com Fanatic, Tabata Aficionada, and Chicago Foodie. The next Rick Steves. Please call me Smalls.