I Wore the Same Dress for 101 Days Straight

What Happens When a Clothes Horse Goes on a Fashion Detox

10 Takeaways from Doing the 100 Day Challenge

I did it! Last September, I challenged myself to wear the same dress for 100 days straight. And I succeeded. It’s a feat I’ve actually pulled off. It’s 101 days to be exact. I wore it for 1 extra day for good measure, just in case so I didn’t come up short.

While the challenge was just a couple yards fabric, wearing it daily is the hardest thing that I’ve ever done.

Harder than running a marathon. Harder than kicking smoking – after my tenth try or so. Harder than waking up every three hours to double feed my preemie (nurse, then pump, then sterilize equipment, then an hour of unsatisfying sleep until rising to sleep-walk through the cycle again. While onlookers tell me they were jealous that I was feeding the natural way).

I selected the Clara shirtdress for my challenge. While 100% wool, it looks and feels like a high-quality cotton. It resists stains and odors quite well and needs only minimal washing. It doesn’t itch. It breathes well. And I was able to wear it as a tunic, tucked in shirt, or a dress. No one commented on me wearing the same item on repeat, except for people I had told about the challenge.

Wearing this dress every day has changed my approach to fashion and the accumulation of material goods. And I was surprised to learn what I do and do not value in terms of clothing and appearance.

Photos of the dress are sprinkled throughout the post since I’m sending Wooland the link to this post as visual proof. that I rocked their challenge.

Why Did I Do the 100 Day Dress Challenge?

I decided to challenge myself to wear the same dress for 100 days in a row for a number of reasons: to have something interesting to blog about every day for 100 days, to find fun ways to re-style the same dress, and to put myself on a fashion detox. I also wanted the free $100 gift card from Wooland for completing the brand’s fashion dare.

With the $100 gift card, I reasoned, I would get another high-end wool garment staple. And continue slowly upgrading the fast fashion wears of my 20’s into a polished, grown-up wardrobe. One with timeless class and sex appeal, beckoning the cool, chic vibes of Francoise Hardy.

Sadly, my paper-thin freakum dresses from the junior racks just weren’t cutting it. I need more structure.

And I have too many clothes. A common problem, right? GAP jeans are cheaper now than they were in the 1990s. Sales and promos are everywhere. Fashion lines used to have 4 drops per year (one for each season). Now, many have 12 drops per year. And some brands, like ZARA, do 52 micro-drops. 52 seasons of fashion per year. If you sell it, they will come. All this cheap, trendy clothing is horrible for the environment.

And then there’s the mental health aspect. It’s hard to keep track of what I have or don’t have. The clutter. The wrinkles. The lack of motivation to iron or to bring things to the cleaner’s. After all, it was only $17.96 on clearance.

It was all so much. I felt like I was being swallowed alive by GAP T-shirts and ASOS jumpers.

How Did the Challenge Go?

I pulled off the challenge, but with much beating of the breasts – and not always metaphorically speaking.

My motivation for completing the 100 day dress challenge continually evolved throughout its duration. Every few days, for the first half of he challenge, I needed to recommit myself to the dress and find new reasons to stick it out.

At first, I just wanted to pull off something really cool and reap the rewards: fun blog topics, fun daily fashion challenges, and a $100 gift card. Then, it became a commitment to sustainability and being a more ethical consumer. Finally, it was just to prove I could do it. To not quit. If I hadn’t widely publicized I was doing the challenge, I would have quietly dropped out. But, with all the build-up I had to see it through.

The first 50 days, I tried hard to style my Clara shirt dress differently every day. Pairing it with the right boots, vests, sweaters, trousers, or skirts. I even worse the Clara dress styled a few different ways for our family pictures. I thoughtfully edited my wardrobe, resurrecting pieces that had lain buried in my closet for years.

During the final 50 days of the challenge, I didn’t think about the dress as much. I hand-washed it in the sink every 7 to 10 days. And steamed out the wrinkles on most evenings. During the final 50 days, I didn’t make it a point style the dress differently every day. I didn’t feel the need to create new outfits. I was fine with wearing the same ensemble, as long as it was clean and presentable. (Besides, I was quite sick and very unpresentable.)

Over the 100 days, Clara really lived.

Over 100 Days, My Clara Dress Endured…

My Clara dress has drank beer, wine, and whiskey. Picked apples. Attended live sporting and comedy events. Met Santa Claus twice. Went to Urgent Care. Traveled the country. And stared a death threat in the eye, before pedaling past it at a blistering 22 mph.

The list of feats is quite impressive. Clara has gone through:

  • A couple of low-key existential crises.
  • Apple picking at the apple orchard.
  • One death threat. (A driver screamed at me he hoped I’d die as I cycled alongside him.)
  • Over 500 miles of cycling.
  • A family photo session. (You can peep the pics here.)
  • Quandary over the sustainability of the 100 day dress challenge
  • Bill Burr comedy show live at the Target Center.
  • Trick-or-treating and trunk-or-treating.
  • Minnesota Wild hockey game.
  • Seasonal time change and SAD.
  • Live Nutcracker ballet performance.
  • Two meet-and-greets with Santa.
  • Two car breakdowns. (Both vehicles, one of which was repaired within 48 hours and the other has been at the body shop for over a month.)
  • Two rounds of pink eye.
  • A visit to Urgent Care for
  • A bout with Influenza.
  • That turned into Pneumonia.
  • And 2+ weeks of bed rest whilst
  • Bing-watching seasons 1-4 of Beverly Hills 90210. (Still devastated that Brenda and Dylan never got back together. Why did Tori have to get Shannen Dougherty kicked off the show?!?)
  • Christmas volunteer event at a local youth center.
  • Work trip to Los Angeles.
  • Office Christmas party. (Paired with my cardigan, it won an ugly sweater contest.)
  • Strolling down Rodeo Drive (in Beverly Hills) like a total badass boss.
  • Burgers and fries at the Apple Pan (set of the Peach Pit for season 1 of Beverly Hills 90210).
  • Trip to Disneyland!
  • Outdoor Christmas festival.

Also, I washed it three times on gentle cycle in the washing machine and about a dozen times in the sink. The hand-washing wasn’t hard. I added a drop of wool shampoo and swirled it in the cold water. After an hour or two of soaking, I could gently wring the dress and then hang it to air dry. It didn’t really wrinkle that much as it air dried; it just looked slightly rumpled.

While it doesn’t look brand new anymore, the doesn’t show any wear. There is no linting. No fading. No fabric thinning. It looks lightly worn, not like a garment that did battle with life for over 100 days straight.

10 Takeaways from My 100 Day Dress Challenge

It’s now January and I completed the challenge on December 16th. (On the 17th, to be precise. I wore the dress one extra day.)

No. 1 | I don’t want more stuff, I want better stuff.

More things do not mean more happiness. There are so many new and cheap goods everywhere. At every minute of the day. It feels like bargain-hunting isn’t just a hobby; it’s how we hunt and gather. It’s a life-or-death pursuit.

I’ve realized that I don’t need garments in triplicates and multiple versions. I don’t need a short-sleeve cotton tee in 10 different hues. I just need a couple. Worn with a skirt or jeans or trousers, the same garment can be worn in endless combinations.

With fewer garments, I can more easily see what’s in my closet and dresser. I take better care of my clothing and they get more wear. I feel better about a wardrobe pared down to 20 items vs having 100. (Although I’m still far away from reaching 20.)

The fewer items I have, the more I wear them and the more I build a sense of connectivity. And I can invest in higher-quality items that are more versatile, more structured, and made from more sustainable fabrics (materials that can be endlessly recycled or are ultimately biodegradable).

In terms of other material goods, I value buying what I need and not more. I’ll buy the 2-pack of scrunchies for $8.99 instead of the 7-pack for $9.99 on Amazon because I don’t need 7. Also, I look for items that are multi-purpose. In need of some new cosmetic brushes, I found a 4-in-1 cosmetic brush that works for foundation, eye liner, and eye shadow.

I’m also putting an emphasis on buying what will last. When buying a new wool sweater for Margot, I selected a unisex cut in light, dusky blue. I bought it one size up so she can wear it now loosely and again next year. And after, she can pass it to Henry for 2 years of wear. While it was an upfront investment of $120, gulp, it will see 4 years of wear. It’s incredibly soft, breathable, and high quality. It’s light-weight but warm, doesn’t itch, and is easily a 3-season garment. And once they’re both done wearing it, I can consign it online.

No. 2 | Dress for the life I have, not the life I want to have.

Buying fewer pieces, I think about clothing more episodically. I buy for the day I want to have, not the life I want to have. It’s easy to let yourself be talked into that cocktail dress or those stiletto boots because they are so cute and they’re such a good deal. So much so that you will create an occasion to wear them. That, of course, doesn’t happen. At least not for me. My closet is full of so-cute or so-cheap misfires.

I think about my daily life and what it encompasses. I want my life to be filled with black tie dinners, charity galas, art gallery showings, and oceanside dinners at Club Med resorts. I’d settle for a full day alone in a perfectly clean house, glass of Chianti, and my vinyls on play with a working needle.

In reality, my life is me working from home during the week in a messy house. Toys and Cheerio crumbs everywhere. A couple of jaunts into the office. Daycare pick-ups. Target runs. Most weeks, a family meal out to Panera is the fanciest thing we do. (And I look forward to it.)

And while I can certainly wear whatever I want wherever I want, I know that I’m not going to want to wear a taffeta ballgown or velvet smoking shoes to the supermarket. The dressiest I want to go is low chunky heels and a blazer, or a simple A-line dress that can be dressed up or dressed down.

Yes, my life is punctuated by a fewer fancier moments like attending the ballet. But here, I would rather dress up a knee-length sheath dress I can also wear to weddings and funerals and the office instead of something shiny, fancy, and on-trend.

No. 3 | Wearing the same thing everyday is not restrictive. I don’t need as much variety as I had thought.

I was surprised to learn that I actually don’t need that much variety. I thought I would find wearing just one anchor garment day-in and day-out too restrictive. But I realized it didn’t bother me because I really like the Clara dress. At first, I didn’t like it. But then I settled on how I liked wearing it: without the belt, with tights, and with my favorite wool jacket and a scarf.

This outlook could be skewed by the fact I’ve mostly worked from home over the past 100 days instead of going into the office. But this challenge felt like permission to wear a favorite shirt again and again, with social impunity.

This has been a stunning revelation, because my wardrobe has always been a glut of trendy and eye-catching garments.

No. 4| I value taking care of my garments.

Before this challenge, I don’t think I had ironed any clothing in years. At least not for half a decade. And I hadn’t brought anything to the drycleaners for over a decade.

With such an abundance of cheaply acquired clothing, I could always find an uncreased alternative. And when selecting new garments, I would opt for things that did not wrinkle.

But I’ve brought in several items to be professionally cleaned since beginning this challenge. And it provides a definite feeling of satisfaction. I like having a wardrobe that’s not easy come, easy go. We value what we take care of.

And I don’t dislike ironing that much. I got a small steamer that I used to take out the dress wrinkles every night. It would take about 30 to 60 seconds a day to make the dress presentable. And I’ve also used the iron and ironing board a handful of times (for other garments) since the challenge and it isn’t terrible. The reward is worth the effort. Clothing that requires ironing is worth having.

No. 5| I want my kids to have fewer things of higher-quality.

My outlook on acquiring fewer goods of better quality has extended to other material possessions, too. I opted out of picking up a few cheapo Christmas tree ornaments at Target this year. Every fall, I had done this because they’re so festive and cute. And they help full out our tree. But at this clip, I’d accumulate a 100 dollar bin ornaments in a couple decades. Which is not necessarily bad, but instead I would rather collect ornaments tied to travel and vacations. And leave room for all the ones that the kids make at school over the coming years.

I also bought my kids a lot fewer things for Christmas. Over the past few holidays, I found myself buying a lot of things to go under the tree. I especially love the gorgeous, heirloom-quality wooden toys in the form of pull ducks and vintage cars and kitchen foods.

But my kids don’t love the beautiful, birchwood toys that look like they belong in a West Elm styled playroom. They like the bright and garish with blinking lights and noises. And they love toys that come with pieces and parts that go missing. (They don’t have a single puzzle still intact.)

So instead of browsing a trendy children’s boutique, I started my Christmas toy shopping by asking myself: What will the kids actually play with, that they don’t have a different colored version of, that doesn’t have a million pieces?

I came up with a shorter list of fewer items. Some were on the definite spendy side. But my kids have played with and adored all of these toys. There were no duds in the mix. And there are fewer toy parts floating around than usual.

No. 6 | I want timeless pieces so I don’t date myself in photographs.

While I don’t aspire to New England prepdom, I don’t want to look back at photos of myself in 10 years and cringe. The way you flinch when you see pictures of mall bangs and mullets and polyester paisley print shirts. I want timeless, like Brigitte Bardot, Audrey Hepburn, and James Dean.

And timeless choices are also non-age specific. I don’t want to dress like a middle-age woman. And I also don’t want to dress like I’m fighting middle-age either. I want choices that look classy on a 25-year-old or on a 65-year-old.

No. 7 | I can’t donate my way out of over-consumption.

As I committed myself to being a less unsustainable consumer, I took the time to learn a lot more about the garment industry and about the perils of donating clothes. I thought clothing donation was a moral, ethical thing to do. And certainly, it’s not immoral or unethical to donate clothes.

But we donate so much used clothing that there’s far too much in circulation. There’s way more used clothing being donated than people who want or need it. We toss out over 11 million tons every year in the US compared to 1.6 million tons 60 years ago. (That’s enough for every person experiencing poverty to get the equivalent of 382 pairs of mid-weight jeans and 1,151 T-shirts every single year.)

This over-abundance leads to a very troubling after-life.

Most donated clothes wind up shredded, or sold or donated overseas to developing nations. There, they eventually wind up in trash heaps. As the materials break down, they pollute the water people drink and they contaminate the soil. This harms the soil’s biodiversity, making it less able to store carbon and less fruitful for growing crops.

I still want to donate my unwanted clothing instead of trashing them, yes. But I want to donate what I think someone will actually want to buy (no stains, no rips, no smells, a style someone will want). And I’m less inclined to pull the trigger on new purchases.

It also makes me even more in favor of reselling used clothings on popular clothing resale apps. With one app, Kidizen, there is a style concierge service where a Kidizen rep will pick up your clothes and list and sell them for you.

No. 8 | Buy what I really love and will really wear, not what’s on sale from brands or stores I love.

While I definitely think secondhand first, I’ve started to buy what I really love and I will really wear instead of what’s on sale or available on thrift store racks.

I want to know that the apparel I buy is going to get worn through multiple seasons or years (if not decades) of wear. While a $118 shirt is a lot more than the $34 version (with the so-so style and killer price), it’s worth it. If I wear the $118 shirt a few hundred times over 8 years, that’s cheaper than buying a $34 shirt I only wear once. Or until I find new $34 version of that shirt that I like better because it’s newer.

I think about the wardrobe staples I want to buy that will get a lot of wear, and then look. For example, I recently decided to invest in a blazer. I tried on several in stores and looked at several options online. The one I liked best is $178 at Madewell, but I went on ThredUP and found the same blazer (same color and style) for only $53.

If it had not been available secondhand, I might have made the investment in getting it new. But you can find a lot of current, in-store styles being sold on used clothing apps. After I find what I want new, I always look for a pre-loved version.

No. 9| I wash my clothing a lot less.

Clothing gets washed after every wear. At some point during puberty, this got drilled into me. Even if the garment doesn’t smell or have stains, it needs to go through the wash because that item has spent several hours soaking up your body soil. You don’t want to stink, do you?

Before the challenge, I tossed everything I wore (except formal dresses or sweater worn with a T-shirt underneath) into the laundry. Now, I wait until the garment get stained or starts to smell. There are tees and button-down shirts I’ve worn three or more times before putting through the wash. (Underwear is the exception; that does get washed daily.)

If my clothing has a small stain, I’ll spot treat it instead of tossing it into the dirty pile. I’ll let it soak in a shallow sink bath, or blot it with water and stain remover and let it air dry before wearing it again. I’m saving on water consumption and laundry detergent. And my clothes look newer, longer. The washing machine is rough on your clothes. Fabrics can only handle so many abrasions before they begin to break down and rip or tear. Not to mention the fading.

No.10 | I’m okay with wearing the same outfit more than 1 day in a row.

Not just my aubergine-colored Clara dress. Since finishing this challenge, I’ve worn a few different blouse and denim jean combos for 2 or more days in a row. I didn’t sweat in the garments. They weren’t soiled. There’s no one that saw me wearing the same outfit 2 or more days in a row, and honestly, I’m not sure I would care if they did.

Thinking About Doing the 100 Day Dress Challenge?

If you’re thinking about it, I say give it a go.

Everyone who completes it finds it to be a rewarding and transformative experience. It’s changed how I think about fashion and how I think about the consumption of material goods. I take better care of my clothing and make more deliberate choices as a consumer about anything that I purchase.

And, there’s nothing like going on a week-long trip with a capsule wardrobe of only 5 items: my Wooland dress, 2 cardigans, and a pair of jeans. It’s 10 items total if you count the accessories!too: tights, a belt, walking shoes, boots, and scarf.

You don’t have to have Influencer-worthy selfies every day. Or even for one single day. That helped me when I had major bouts with Influenza, then Pneumonia, and then Seasonal Depression. For a period, I wasn’t blogging because work and “the holidays” and the kids took all my energy. But I was still able to take a daily picture to show I was wearing the dress.

In some of the photos, you don’t see my face. Or full body. And this is okay. A lot of my pics look similar because it’s a pic of a headless torso in the dress in my bedroom, living room, or basement.

Many other challenge participants say that their coworkers never noticed they were wearing the same dress for 100 days straight. As much as we worry about our appearance, other people really don’t care how (un)stylishly dressed we are. Plus, you can wear your dress tucked into skirts or trousers, with blazers or cardigans, and plenty of other ways to get a wide variety of looks. Some women even wear their dress tied around their neck as a scarf, and hey, it counts!

There is a 30-day dress challenge you can do for a $30 prize if you’re looking to ease in. For me, I felt like I had to do the 100-day because I anticipated there would be some struggle with any challenge that involved wearing the same ensemble on repeat. And if the struggle came with 30 days, I didn’t think I could do 100 days after. But for others, starting off with just 30 days is absolutely the right approach. There’s even a 30-day kid challenge which Margot completed. (Mom just hasn’t had her act together enough to organize and submit the photos.)

Some Wooland dresses are more versatile than others. There are sheath dresses with more stretch and structure, or T-shirt dresses that are more casual. There are jumpsuits, too.

While halfway through the challenge, I regretted choosing the Clara dress because it’s the only one that wrinkles, now I’m glad that I did because I think it’s the dress style that best lends itself to being worn as a dress, a tunic, or a blouse.

If you do the challenge, let me know! Message me in the comments, or shoot me an email. I would love to follow along and see what you wear, how you style it, and how your journey unfolds. There’s a lifesaving Facebook group, too, for participants of the Wooland challenge. It’s a great place to connect with other Woolies and get ideas on how to style your dress. And to find your challenge twins (who start the challenge on the same day that you do).

My 100 Day Dress Challenge

>>> Trending Read: Could you wear the same dress 100 days in a row for a $100 prize? I’m doing the 100-day dress challenge! Find out more and see how I’m getting 100 outfits out of 1 dress. 100 Day Dress Challenge

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