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


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  • Lea Telivuo-Kupari

    Those Valentino shoes look so right though. And the Elizabeth&James sweater with the Dries dress! Love!

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  • Jwaxywax

    I was very much feeling this way this morning but felt constrained by ice cold London weather to stick to jeans. Thank you for more reliable and relevant advice

  • Natali

    This first outfit is totally going to the middle of my inspo board!! LOVE the shoes, totally magical! 🙂


  • Julie Meowmeows

    Rawr, love that kimono. I’m wearing purple corduroys today.

  • Stephanie
  • Natalie

    Love your outfits, my favourite is the second one – that kimono is awesome! Actually I just started wearing jeans again, after a forced skinny-jeans-overdose break. Culottes were my savior in those dark times and happily ever after flares became my new daily dosis of denim (would love to pare them with this pullover http://www.net-a-porter.com/de/de/product/643510/Gucci/pullover-aus-modal-jersey-mit-blumendruck )
    If I´d my denim crisis now (and the funds to afford it), I would try all-dries-everything outfits with a small dosis Stella McCartney and Valentino, I´m still in love with your citrus fruits stella skirt and that dotted iconic Valentino skirt and of course your Valentino shoes (both the boots and the tango shoes)…

  • Good question. But I am not sure about the solutions you gave. You wear it nicely but I would not :-)…

  • Olivia O

    Lately I cannot stop layering sweaters/shirts/anything I can find over dresses so I’m interpreting this as MR validating my life choices.

  • Brittany

    I am in different types of serious relationships with all my jeans, but also around this time of year where I’m getting out of bed later, because its so god dang dark, I don’t have time to “effortlessly” think about putting an outfit together and rely on my go-tos….jeans. I hear you though, I get sick of them too. I don’t rule them out because my style is more pared-down and minimal this time of year, but on the other hand your style is more decadent and creative which seems like you might need to just switch it up for a while before you give away more of your favorite jeans! You know best how hard it is to replace them.

    Lock them in a safe or hide them from yourself. And only when you find that deep desire to wear them after some time, with an adorable (possibly late) spring top should you resurrect maybe a single pair….

    or honestly don’t do any of that and rid yourself of all the indigo in your life.

    but aren’t they so comfy?

    and usually cool?

  • These are the outfits I LIVE for. I love the proportioning and layers and colors and textures. I also need to get away from my denim but it’s hard when the weather is so shitty and cold. ahhh the sufferiiiing

  • Malu

    I love how much fun you have with putting looks together. I always notice how I would never think of putting some of these things with another but you pull it off perfectly. I like this idea of wearing anything but jeans because, honestly, they can get annoying and uncomfortable to wear at times. I thought that these outfits showed how cool your really can look without them. Great post!

  • love those red Valentino shoes!


  • Love these ideas especially the pants!

  • BK

    Question for Leandra, comment section at large – should I DIY the Elizabeth & James sweater from look 3 or this Dries one?

  • That first look is everything!! Love it
    xo Aya


  • Love these looks — and MR is so HOT right now. Thanks for creating a meaningful fashion space! <3

  • Shannon

    Leandra that Saks Potts Kimono is too much, saving this post for the day I get my coins right.

  • Leslie Joy Ickowitz

    Just returned from Indonesia, where I bought several pairs of fabulous, flowy, print pants (to combat my own recent jeans conundrum—I never ever thought the day would come) and also decided I want to dress like I’m in Bali all year round, which, while unrealistic, is nice to fantasize about.
    Your Dries Van Noten dress is happening.

  • Leandra, I’m getting vibes from you that you’re not quite feeling yourself lately and I just wanted to let you know that you are really awesome. You’re a fantastic story teller, you are a natural beauty, your hair always looks effortlessly cool, your outfits go without saying and your sense of humour and quick wit is something I really admire. You’re doing really great at life. I just thought you should hear that.

  • me

    Work was a major suck-fest today.

    Leandra, you – and your fab outfits – made my day.

    I’m loving you too much !

  • Loved reading this post!

    Freya | freya-ella.blogspot.co.uk

  • I know exactly what you mean except that instead of jeans, for me its black leggings. I am ashamed to say I wore black leggings to work yesterday. I work in a bank. I just had this ‘I can’t believe I actually did that’ thought while I wrote this down. I am totally for this sweater and midi skirt trend.


  • Soul & Sense

    I`m in love with the first look!


  • ClossEnough

    Great ideas. I wear jeans almost every day. It’s pretty boring. So I decided that on weekends I will wear dresses or skirts. So I will copy some of these outfits.

  • soniadelvalle

    I went into a very rewarding phase of no-jeans. I decided that jeans were boring and that everybody wears them every day and that I am NOT everybody so I had to expand my pants-horizon. I ended up adding really nice alternatives to my closet and wearing almost zero jeans. Now I’m trying to find that healthy middle but I fear I look too… basic (sorry for the B word) when I wear jeans.

  • Maria

    Thanks a lot for this post!