Humor, life, mindset, sexuality, Women

How to Be Effortlessly Cool

Ode to the women who make it look easy

by Jennifer M. Wilson


This is a total bait and switch title. Did you think I was going to teach you how to be “effortlessly cool”? Hell no! I have no fucking clue how to be hip! Do cool people still say “hip”? 

I wish I were the type of woman who woke up, tossed on a vintage Ramones t-shirt (I don’t think I’ve ever even heard a song by them, that’s how uncool I am), some ripped skinny jeans and…crap I don’t know what shoes would go with that outfit without looking like I tried too hard.

I want to be the woman who just looks cool and fashionable without even trying. When the outfit looks flawless, everything seems to come together.


How do you define those women who look fabulous no matter what they wear? It’s like their clothes are a tribute to their essence and their soul. A woman who looks spectacular in a business suit might look ridiculous in the same summer romper worn perfectly on another.

For me to look good, it takes effort. I can look fantastic in that business suit too, but it won’t feel comfortable on me; it’ll feel like a costume. When I wear my “standard uniform” of skinny jeans and a weird t-shirt (usually made myself because I’m a crafting nerd with a Cricut), I don’t look “effortlessly chic”. I look homeless.

So if wearing what is comfortable doesn’t inherently make a person stylish, but dressing up doesn’t make them fashionable either…what is the special sauce for those that make it look so easy and perfect?


High school is one place you never want to stand out. At least, that was the case in the 1990s. This was the era of In Living Color, when J Lo was an unknown backup dancer. Baggy oversized sweatshirts. Overalls. Air Jordans. One girl in my school followed the beat of her own drum.

I jumped to my yearbook to remember her name. I’m looking through mobs of grainy black and white pictures (my GOD kids today are lucky Photoshop exists), figuring I probably wouldn’t recognize her. Nope. BOOM. Her gorgeous smile and bouncy blond curls popped out of the page.

Her name was Sarah.

She wore hippie-style outfits. Lots of peace signs and cartoon-y flowers. Nothing like our faux hip hop clothes. In our final year of high school, she decided she wouldn’t shave her legs. Did I mention that we had a Best Legs Competition? (yeah, that’s a little inappropriate in hindsight)

Of course, Sarah won. She had legs for miles and could pull off crazy knee-high socks with bright patterns.

Anyone else straying from the teen norm and growing leg hair would be a high school pariah. Not Sarah. She didn’t give a shit. She wore shorts and skirts. It wasn’t attention-seeking; she simply didn’t care. The rest of us girls were awestruck.

Is that the definition of being “effortlessly chic”?

I would look like a clown in Sarah’s outfits. But on her, it was like she walked out of an Abercrombie for Hippies catalog. Is the key that it’s something that feels natural to who you are? Not “comfortable” like my lazy jeans and t-shirt look. But “natural”, like comfortable to the wearer but spiced up a bit.

That might be the secret.


Purging her closet to embrace minimalism, a friend of mine gave me a bag full of clothes. She works in the entertainment industry so I trust her taste in fashion better than I do my own.

While there were things I didn’t keep, I held onto a fitted orange corduroy blazer. It sounds hideous, right? I kept it for years when one day, while heading out the door wearing the usual jeans and t-shirt uniform, I grabbed it on a whim. Surprisingly, it fit me perfectly. This jacket fits as if tailored custom for me.

As I walked around work that day, I received dozens of compliments on the jacket. Even a few male employees risked HR suspension by saying, “Wow…that color on you…you look great!” and “You look really good today.”

Had I unknowingly mastered “effortlessly chic” without knowing it?


Perhaps I’ve cracked the code: The key to looking effortlessly chic isn’t wearing comfortable clothes. It isn’t wearing clothes that are too dressed up for your style. It’s the intersection of your go-to outfits with pieces outside of your typical comfort zone. Not so much that you feel self-conscious; just enough to feel like you mixed it up a little outside of your norm.

What that in mind, scroll up to the picture at the top. Unsplash Photo Woman may be used to leather and high boots, but maybe wearing animal print isn’t her jam — Boom.

Effortlessly chic. Nailed it.


About Jennifer M. Wilson

From Medium: My midlife crisis and adventures along the way. I write because in real life my humor is allegedly too sarcastic and inappropriate.

Read more of Jennifer’s work on Medium: NinjaGirl@gmail.com


This post was also published by Living Out Loud on Medium.

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