What to Wear When You’re Sick of Jeans but Still Want to Look Cool

I’m not sure if we are living through the self-improvement era or if worrying more about your mental health is a condition that comes with age, but I do know that I have recently become obsessed with making myself feel good. It sounds kind of trite now that I’ve typed it out loud but I never really thought about what it takes to “feel good” until, you know, I did.

Historically, I’ve leaned on clothes as the agent that heralds unilaterally positive change. I counter bad moods with good clothes, feeling like shit with shoes that I prefer to call the shit. But recently, that valve — the most reliable pressure point I know to make things feel more okay — isn’t quite working. I’m not sure if that’s because I’m changing or simply because the old tricks don’t quite cut it anymore, but I do know that the last few weeks have built a new routine that I’d like to kick before it gets out of hand.

It goes like this: I stand in front of my closet. I look at the clothes. I see the sweaters, I put on one. I like the sweater. I am grateful for warmth. I look at skirts and veto them all. Look at pants, feel intrigued, then ultimately determine that I will look far too corporate if I’m to wear them with a sweater. And boots. So I dip into my jeans pile only to find that every pair that has ever worked, that has ever pushed me to feel satisfied by my reflection, sucks.

So what does this mean? Is it possible that the end of jeans is coming? That in a few months’ time, we’ll all be confused? If not jeans, then what? What in the good name of Levi Strauss are we expected to wear? I know for sure that a cropped flare fit with ankle boots — a surefire marriage, I was certain! — makes me cringe. That if I’m going to wear skinny jeans, I may as well buy flip flops and that too-long jeans worn with ballet flats and a simple black turtleneck (impossible in 19-degree weather) make me feel like I have given up.

I have surrendered!

The thing is, I haven’t and I won’t. So consider this story a meditation of trying to work through a rough patch in the trajectory of my relationship with jeans. I need to give them a break. I’m going to give them a break, and until I can find that simple, no-brainer, pull-it-out-of-your-closet-with-your-eyes-closed combination, I’m going to try really hard. With this:

What to Wear When Youre Sick of Jeans Leandra Medine Style Inspiration Man Repeller - 12

Elizabeth & James sweater, Dries Van Noten dress, Tory Burch shoes, Prada sunglassesTopshop tights

And this:

What to Wear When Youre Sick of Jeans Leandra Medine Style Inspiration Man Repeller - 31

Saks Potts kimono (another kimono here), Gant shirt, Saint Laurent bow tie (or scarf option here), Loewe pants (another option here), Dries Van Noten boots

And this.

What to Wear When Youre Sick of Jeans Leandra Medine Style Inspiration Man Repeller - 36

J.Crew turtleneck, Isabel Marant button down, Marni cardigan, Dries Van Noten dress, Valentino shoes, Illesteva sunglasses, Olympia Le-Tan clutch, Topshop tights

Photographed by Krista Anna Lewis


Leandra M. Cohen

Leandra M. Cohen is the founder of Man Repeller.

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