Featured

I Stopped Being High Maintenance and Started Wearing Red Lipstick. Here’s what I learned.

By  | 


 Kari wearing red lipstick and chic trench coat in downtown Chicago.

Kari wearing red lipstick and chic trench coat in downtown Chicago.

Kari wearing red lipstick and chic trench coat in downtown Chicago.Tentative title: How to wear red lipstick … and why everyone should be wearing red lipstick.

From Loitering to Adulting

I was a spectacular Bohemian. I say this now with great pride because it is the only job for which I have ever been completely qualified.

Over the years, I’ve sat in countless bars and loitered in numerous coffee shops, requiring nothing from them except to be seedy and wreak of desperation. Here, my thoughts were free from judgement. My fingers hit the keyboard like raindrops on a windshield. Sentences flowed together and rippled into seas of essays and feature articles. Daily, I’d swap offices and dress codes based on my moods. Jeans? Sure. Dresses? K. Sweatpants? Even better.

Unfortunately, writing freelance was becoming an expensive one-way ticket to Broketown. A few clients made partial payments, others caught amnesia. The writer in me despised the collection officer I had become. So, I got a job — an adult job. Again.

I glided into the interview wearing thrift-ed couture, borrowed Chanel, and a boatload of confidence. My dress was a bright green, heels were nude, and my lipstick was something near a sheer millennial pink. Overall, it went well. I got the job. 6 months later, my inner Bohemian was dead and I was the human embodiment of the color beige. Lost in a rut of business skirts and mauve eye-shadow, it was time for a change.

The Crimson Kisser is a Glow Up Elixir

First, I revamped my wardrobe, simplifying my morning routine while simultaneously upgrading my look. Then, I stopped doing the most and started doing the absolute least (almost).  Basically, I learned the power of a well lined matte red lip and my life changed forever. I’ve harnessed all the fuss and frustration of getting dressed and out the door into mastering the lip brush and liquid lipcolour.

After two months of sporting a crimson kisser, here’s what I’ve learned:

  • No one cares what I wear. Especially men. During a particularly exasperating two weeks I stopped washing my hair and wore the same outfit three times. One co-worker’s observation? “You always look so fancy.” Neat!
  • Red lips are the glow up elixir. On short notice, my awesome sauce boss sent a pair of Blackhawks tickets my way. I arrived in a team hoodie, destroyed jeans and a red lip. Not exactly 90’s Naomi but the selfie I took at the game is now sitting on my mother’s bookshelf. She liked it that much… Albeit, she is my mom. Her opinion isn’t the least biased.
  • Wearing red lipstick every day is like speaking non-stop in hyperbole. It can be exhausting for friends, family, and anyone I spend real time with on a regular basis. “Red is your color girl.” This is the first thing my friend said when she climbed into my car last week. I surmise this is her ironic way of telling me to ease off the red lips for a while. Too bad, doll. I’m addicted.

The moral of the story? Red lips are all you need, no matter where you’re going. I promise.


Kari Herrera is the creator of Chicagoings.com, Chicago’s indie city guide and blog. She often writes about the city’s points-of-interest as experienced by a local. She is a Social Media Marketing Manager and freelance writer. When she’s not working, Kari donates much of her time to the education of French-speaking immigrants in Chicago.

The Chicagoings Newsletter: It's Free. It's Useful. It's Spam-Free.

If you're not a subscriber to the Chicagoings.com newsletter you're missing out on monthly giveaways and weekly updates featuring the best of Chicago.

We will never spam you. EVER!