Drawing by Sharon Dennard

75 days. 75+ outfits. The viral challenge that made me reconnect with my closet and fall back in love with getting dressed.

I have always loved getting dressed. When other children bemoaned getting clothes instead of toys for their birthday – I begged for them. A gold sequin shift dress I found with my Godmother at the local Palais Royal made me feel like a chubby Twiggy. Heavy leather Coach handbags stolen from my mother. A JPG-inspired mesh top with a tattoo-like print that I had coveted for months. All these things made their way into my closet well before puberty.

"It felt impossible for anyone to truly know me by only seeing me from the clavicle up."

Throughout my life, getting dressed has been my superpower. The way I express myself, and usually, how I make friends.

Until the pandemic. Suddenly, we were trapped with nowhere to go, and although I always thought I only got dressed for myself, the magic disappeared. I now only existed through email or a small little Zoom screen alone. No matter how fancy a blouse or collar I wore on Zoom, that little window smothered one of my main methods of communication. It felt impossible for anyone to truly know me by only seeing me from the clavicle up.

Over the next four years, my life changed, and so did my closet. I wrote on two TV shows, got married, went on strike as a writer, and joined the Happy Isles team. But like many others, I came out the other side of these past four years unsure of what was next: for my life or my closet.

For the first time, I found myself stumped every morning when I went to get dressed. I was overwhelmed by the general chaos of my closet and torn between what I thought I should wear and what I wanted to wear. Suddenly, my closet was filled with things that still had tags – a sin that would have horrified me pre-pandy. Somehow, my closet had become a haphazard mix of my past, present, and future.

Which brings me to "The 75 Hard Challenge." An online trend that was making the rounds as the next big lifestyle level-up, promising to be "Ironman for your brain" and the surefire way to "take control of your life" in 75 days.

Work in progress...

This certainly wasn’t for me. I have always subscribed to a soft girl life. There's little that I feel a martini, a massage, and some Popeyes can't fix. (I call this Liz Taylor-ing.) So, nothing about this challenge piqued my interest.

But then fashion writer and excellent TikTok follow, Mandy Lee (@oldloserinbrooklyn) came out with something different: The 75 Hard Style Challenge.

The rules are as follows:

-Get dressed every day for 75 days.

-Document your daily outfits.

-Do not buy anything new.

-Set your challenge goals/intentions.

-Get creative and rely on your own brain for inspiration.

-Organize and clean out your closet. (Once at the beginning of the 75 days and once at the end.)

@oldloserinbrooklyn Kicking off 2024 with a style challenge! If you want to start the new year off by glowing up, saving money, getting more use out of your closet and firming up your personal style this one’s for you. 75 days of intentionally getting dressed, collecting data, and discovering what you naturally gravitate towards. I’ve used this method many times and it’s one of my favorite easy ways to get back in touch with myself and see my clothes in a new exciting light. Challenge Rules: Get dressed everyday for 75 days Document your daily outfits Do not buy anything new Set your challenge goals/intentions Get creative and rely on your own brain for inspiration Organize + clean out your closet I will be taking part in the challenge and my personal goals are to start wearing pants more, firming up my casual style, and experiment with new shapes and silhouettes. I hope you’ll join me! #personalstyle #fashion #75hardstylechallenge ♬ original sound - Mandy Lee

Mandy had used these principals over the years when she found herself in a style rut and needed to reboot. Not only did the challenge seem like just what I needed, but it was also comforting to know that other people out there felt just as lost in their closets as I did.

I would be lying if I didn't say that part of the appeal of the challenge was the promise that you would find "holes" in your wardrobe. I was sure that after 75 days, I would have a nice juicy shopping list and a small pile of cash as a result of not shopping for 75 days. (Dear reader: She did not save money. It turns out that “no clothing shopping” simply means I use my shopping talents to buy things for me and my husband’s apartment instead.)

A surprising star of the 75 Hard Style Challenge? My Simone Rocha Crocs

So I started the challenge. I went through my closet and got rid of any items that were stained or no longer fit. I pulled out things I'd pushed aside for the tailor or the dry cleaners and got them fixed and back in the rotation.

I put items I never wore but wasn't ready to part with on probation and challenged myself to play around with styling them to see if they had a place after all. I documented all the looks on my TikTok even though my only presence on the app up until that point was some videos of my long-haired calico, Fiorucci.

Me, myself, and my many outfits...

What transpired over those 75 days was truly wild. I found myself inspired in ways I hadn't been for years. My closet seemed to gain clarity. There were things I thought I wore all the time that I barely touched! A vintage Ralph Lauren navy pinstripe blazer, previously on probation, is now an item I wear at least once a week.

Turns out a whole section of my closet was filled with cotton dresses from H&M. If you had asked me at the beginning of the challenge, I would have told you I wore them all the time. But in the process of really considering what I wore, I found myself cooling on them. They were always wrinkled, somehow never quite right. They all had to go.

I dug into my jewelry boxes for bigger, flashier things than I’d worn in years. Playful pieces like my chunky baby blue acrylic earrings from Mondo Mondo or piles of vintage gold bracelets brought a spark to my eye on days when I felt like if I had to wear my pinstripe Ganni pants again, I’d scream.

I experimented with poses...

Although I have a varied collection of shoes, I mostly wear ones from Sam Edelman and Miu Miu. The black leather Mary Janes from Sam Edelman were so well loved after 75 days that they deserved a Viking funeral to put them out of their misery.

I can admit the challenge has shined a harsh spotlight on how much Ganni I own and revealed the brutal truth that I needed to take a Ganni break. (Dear reader: She did not. She bought a new pair of Ganni jeans and a kitten t-shirt immediately after the challenge was over.)

Acne Cat Shirt was a real trooper in this.

The no-buy element of the challenge was hard, but not nearly as hard as I thought it would be. Notably I was tested when a fuchsia Molly Goddard tent dress with my measurements at an incredible price came up on The Real Real. But much like we tell the brides who come into Happy Isles, every dress finds its person, and if it's meant to be, it will still be here, and sure enough, the Molly Goddard was ready and waiting for me post-challenge. (I'm also happy to report that it was even more perfect than I could have imagined.)

Through it all, TikTok held me accountable. I'd pop my iPhone onto the sliding glass door of the “clo-ffice” (my closet / my husband’s office) via my handy new Octobuddy, hit record, and stare into the screen as I debated if my Marni leopard drop earrings were too much with my Ganni cat shirt. (They happened to be perfect.) 

@thestelladallas DAY 73 #75hardstylechallenge #ootd #outfitinspo #plussizefashion #sizeinclusivefashion #fashioninspo #fashion #fashiontiktok ♬ original sound - alice

As I edited the videos, I reflected on the things I’d passed over or came up with new combinations to try the next day. It kept me honest, it pushed me forward. I even won some new internet friends and cheerleaders.

At the end of the 75 days, I reorganized my closet again. Things that didn't make it out of probation went to Crossroads. Things that came back from the tailor had a new life. Things I wore throughout the challenge - my Ganni satin jacket, Levi's wide-leg jeans, and my oversized Acne Studios cat shirt - got reshuffled to prime closet real estate.

"And in the end, I looked at my closet, and it felt like mine again."

The shopping list of “holes” for my closet was not juicy but rather calculated and concise: a new pair of black Mary Janes since I wore holes in the others; a light-washed pair of flared jeans to have an alternative to the Levi’s wide leg; oversized vintage Playboy sunglasses to make up for a pair I passed on at the Palm Springs Vintage Market during my no-buy; and, of course, my Molly Goddard dress.

The dress was finally mine!

And in the end, I looked at my closet, and it felt like mine again.

I now think of my closet like a garden. Something that needs to be tended to, pruned, and watered. Something that transitions with the seasons and flourishes with love and care. So next time my closet gets overgrown, I know just what to do.

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