The Five Day Denim Challenge

As in, five days, five outfits, zero jeans. I KNOW.


You know those people who do stuff just to prove a point but ultimately end up hurting no one but themselves?

I never thought myself to be one of them, but then I had the worst idea in the history of bad ideas.

See, Amelia and I were thinking through what kind of new diets we could possibly embark on for our series, MR Diets. In thinking through things I would likely find near impossible to achieve, I looked down at my crotch (as a self-proscribed “man repeller'” is wont to) and eureka, there it was, my solution: why don’t I try eschewing denim in favor of its fancier fabric friends and cousins for the course of one week.

I am sure it sounds easy enough but then again, watching a trainer do sit ups looks easy, too. It takes getting into the thick of the motion yourself to realize how fundamentally challenging ab-muscle engagement (or keeping your legs away from denim for an extended period of time) can be. So here we are, five days older and maybe — maybe — just one degree wiser.

It seems easy enough at first. I thought I was beating the system on Monday when I opted for a set of khaki pants plus matching top. If it’s not going to be denim, let it be another utilitarian fabric, right? Monday night was decidedly simple, too. There it sat, a yellow set in a garment bag by Stella McCartney, extolling the virtues of feeling a little bit like Natalie Joos and a whole lot like Bianca Jagger’s accountant.

Walk in the park.

Tuesday wasn’t too bad, either. I like culottes almost as much as I like avocado toast and possibly even more than Amelia likes Oprah. So I put on what I have started to call the signature green pair with a striped linen button down shirt, a black belt (for the edge of cool that jeans typically provide) and shoes that frankly have no place walking streets outside of Palm Beach.

I got this.

Until lo and behold, Wednesday and Thursday reared their heads. I think this is the stage wherein an addict begins to feel withdrawal. The placebo wears off, the power-of-regained-control is no longer novel and there you are, begging for a rip, a camel toe, a cowboy crotch — anything that bears semblance to the vintage 501s of yore, but you’re stuck. So what do you do? Get hyper-thematic. I relied on a traditional Ukrainian dress by fashion prodigy Vita Kin for Wednesday (though you should know it took many iterations of trying to personalize and own this dress before I ultimately settled on just letting it own me) and a pair of white silk faille overalls by Natasha Zinko, deliberately worn with a corporately-inclined blue button-down to counter the flower in my hair. This one was fun (if not difficult) to execute because all I really wanted to do was tuck the blue shirt into blue jeans, wear those Palm Beach sandals with the flower in my hair and tell New York to F itself.

By Friday, I am almost positive I was beginning to develop whatever the yeast-infection equivalent of starving your nether regions a vital nutrient would be. But I drudged on in a tinker bell dress and clogs peppered with a bandana around my wrist and I don’t know why, but I also included mushroom head.

At the bottom line, I learned this: there is definitely value in forcing yourself out of your style comfort zone, if not because necessity truly is “the mother of invention” (and creativity, or whatever), then certainly because it’s true, you know: absence makes the ass grow fonder.

Think this was tough? Check out that time Leandra tried the mirror challenge, the no-pants challenge or just try and read all of our past writer’s prompts without crying tears of joy. Photographed by Krista Anna Lewis.

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  • Calling Wednesday’s dress the ‘Emma Dress’ bc sometimes I can be selfish and also bc I think my knees buckled when I saw the sleeves on that thing.

  • ha, i wish this was a problem for me… i HAVE to skip the denim every weekday, thanks to my regular job 🙂
    xo, coco |

  • Lua Jane

    That Vita Kin dress does deserve to be worn every day, an entire week, until it has to be removed for hygienic if not for style related reasons. Also those green culottes.
    Plus I realized that Leandra is a clothes wizard. So in many cases it’s not just the item per se, as the styling and maner she wears it in.

  • Lizzy

    I love these “what I wore every day for a week” posts. I stalk New York Closets. There is almost always one outfit inspiration in all of the looks. I especially love when I see something that is like an “Aha!” moment. Okay, now I’m going to go wear that blue and white striped shirt with some colorful pants and red shoes!

  • SevenOclockDropTop

    where is the watch from, please!?

  • Catalina

    girl, you done found the overalls

  • Abigail

    “white silk faille overalls” unexpected combination of words but wow those are insane

  • The shot of the Vita Kin dress in front of that deep green shadowy wall made my heart skip a beat – well done, Krista!

    • Krista Anna Lewis

      Thank you!! <3

  • Tough challenge – I’d be lost without my denim!

  • monkeyshines
  • gail.

    I’ve been on this challenge every week since January (denim is against the dress code at work). I occasionally skirt the system by layering a denim jacket over a cardigan so I can at least enjoy denim’s sweet embrace whilst walking to & from the train.

  • Manuela

    Just loooooved the Natasha Zinko overall…


    If you’re dieting at the present then you will know just how tough it really is. You need to watch John Barbans great FREE short video on LIPTIN and the Metabolism it’s a real eye opener on why it can be so tough to lose weight even when your eating the right foods. < click for video ::))

  • Love the look #10! That dress is so simple and beautiful!:)


  • Andrea Loh

    Absolutely love the yellow set! I on the other hand had to force myself to buy more jeans at one point because I had too many culottes and printed cigarette pants that when I wanted to take a break and just wear the basics, I literally had no jeans to wear.

  • CarlotaLMorais

    You look amazing and sexy with the red dress from wednesday and that white dress from friday! I shall try not to wear denim for a full week, we’ll see how that goes!

  • Love the Vita Kin dress. More dresses for Leandra!

  • Ede

    Honestly, this seems very logical now especially since its currently so hot in London.

  • Selina Moses

    I love Wednesday and Thursday’s outfits. I think people rely too much on jeans and don’t explore other trouser options enough

  • Stop wearing black was one of my style resolutions this year. I would really recommend other ways to limit it is to stop going to the same stores and same brands! Its a revelation!