Secrets of the 100 Day Dress Challenge
Simplify & Slow Down,  Sustainable Fashion

Secrets of the 100 Day Dress Challenge

Could You Wear the Same Dress for 100 Days?  I bet you could and you didn’t even know it.  I bet you could find it freeing, energy-giving, and overall a divine experience.  On the other hand… it may not be for you.  Here are the what, why, how, and all the secrets you need to know about the 100 Day Dress Challenge. 

*Updated June 27th, 2023. Thanks to the Wool& Team, I am now an affiliate partner! I am truly moored to promote a company that aligns so perfectly with my values. If you do decide to purchase anything from Wool&, please use my referral link!


The 100 Day Dress Challenge

Years ago my sister mentioned this sustainable US company that was offering a free dress if you could wear one of their high quality wool dresses for 100 days straight.  I immediately latched on to the idea.  I’ve always loved the idea of a capsule wardrobe and already stuck to a pretty simplistic set of outfits.  

You see, after going through a major minimalism binge- reading, watching, and listening to everything I could about minimalism- I swiftly made my way through my house.  I had cleaned out bedrooms, kitchen cabinets, knick knacks, photo frames, linen closets, and toys until I was satisfied with my clutter-free surroundings.  Of course, this meant cleaning out closets and clothes stored away for years.  (Mostly labeled pre-pregnancy, maternity, and nursing…any mom can understand the amount of fluctuation in her wardrobe throughout those periods of time.). I already felt lighter and clearer.  But I wanted more. 

Bring back the 100 Day Dress Challenge.  Wool& is a US company whose motto is, “live simply. consume carefully. do good.” They are a pillar in the slow fashion movement and have outdone themselves with a traceable supply chain. You know exactly what farm your wool is coming from, who is spinning and knitting materials, where it’s being sewn, and the laws and regulations surrounding their products.  For more in depth information, check out their page here:

All this to say, Wool& is producing sustainable, high quality closet staples and they know it.  In order to get people to try their products (and fall in love), they came up with a 100 Day Dress Challenge.  If you wear and document the same Wool& dress for 100 consecutive days, you can receive a $100 voucher for their store.  When the challenge first started, they were giving away a free dress to anyone that did the challenge.  Once it became more popular, they had to cut down on free dresses ($140-170 value) to a $100 voucher.  According to their website, over 6,000 people from all over the world have now completed this challenge.  


Why wear the same dress for 100 days? 

I was first attracted by the idea of the 100 day dress challenge from a minimalist standpoint.  I had already done so much editing of excess in my life that this seemed like a logical next step. 

Sustainability was a close second for reasons why to do this challenge.  The more I read about this company, and conversely fast-fashion, the more I wanted to make a positive switch. 

Read about Sustainability here: 

10 Ridiculously Simple Ways You Can Live More Sustainably TODAY
How To Be More Sustainable in 2023
The Basics of Living A Sustainable Life
Everything You Need For A More Sustainable Kitchen
Everything You Need For An Eco Friendly Bathroom
How To Extend the Life of Kids’ Leggings
How To Shop At A Thrift Store

Simplicity is a huge draw.  Wearing the same thing every day may seem boring to some people, but for me it was like a dream.  Someone was giving me permission to be my simple, lazy self. I’m all for that!

Lastly, that $100 coupon is nothing to sneeze at!  If I was serious about investing in more sustainable fashion, then that $100 voucher was one more baby step on my sustainability journey. 


The hardest part about doing the challenge was choosing which dress to buy and wear for 100 days.  Wool& has a ton of options:  short sleeves, long sleeves, sleeveless, dress length, dress style, color options, etc.  I opted for the most basic of basics:  a long sleeve, gray swing dress called Rowena.  I decided to do this challenge over the winter months so that narrowed down my options significantly.  Choosing the color was the hardest part.  I love colors.  I love to dress in colors.  BUT I wanted something that could be layered with pretty much anything in my closet.  So plain gray won.

Many people during the challenge choose to come up with creative ways to wear their dresses.  From layering, tucking in, and tying knots to wearing as scarves and doubling up on dresses.  I stuck to #teambasic.  (A term coined in the Wool& Facebook community, more on that later).  For warmer days, I wore my dress with just biker shorts under.  When the days turned colder, I wore it with leggings and then layered more with chunky sweaters.  On days when I was particularly active, I tied my dress at the bottom to make it into a cute long sleeve shirt.  Occasionally, I threw on a necklace.  

So as not to be tempted by other options in my closet, I packed everything else away that I wasn’t planning on wearing during these 100 days.  I came to find this was pretty unnecessary, but may be helpful for others who love all of their clothes.  I did love how my closet looked with so little in it!  It was refreshing!

Every day I took a photo in my dress and uploaded it to a google drive folder.  After the 100 days were over, I sent over my photos to Wool& and received my voucher code for $100.  And that was it!  

100 Day Dress Challenge in Rowena

Benefits of the challenge

After actually going through it, I found so many benefits of this challenge. 

  1. Eliminates Decision Fatigue:  Decision fatigue is a real thing.  As a mom with 3 small children, 3 jobs, and a growing list of demands, clearing my mind of something like choosing a daily outfit was liberating. I highly recommend it.
  2. Way Less Laundry:  Laundry is a way of life and I’m always looking for ways to make this aspect of life easier.  Wearing the same dress for 100 days reduced my laundry SIGNIFICANTLY.  And I didn’t even realize that would be a natural consequence until I started the challenge.
  3. Confidence:  If you pick a dress or clothing item you love and look great in and wear it every day, you can’t go wrong.  I never had to second-guess what I was wearing.  I never had to question whether my outfit looked good on me.  I felt comfortable in it and confident in it.  
  4. Less Buying:  While doing this challenge, I didn’t even think about buying other clothes.  I didn’t need to!  Once the challenge was over, of course, I was more interested in purchasing intentionally and sustainably.  More on that later. 
  5. Support groups & like-minded people:  Lots of challenge participants choose to create an Instagram profile solely for their 100 Day Challenge photos.  This is a great way to connect with others and get inspiration from their outfits if you plan on getting creative.  The Facebook community, however, is the real winner.  The Wool& 100 Day Dress Challenge Facebook group has 15.4K members.  It’s not just for people doing the challenge, but for anyone who has done it in the past or wishes to participate in the future.  It’s a community full of people that lift each other up, encourage, and inspire. 
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There were a few main struggles with the challenge.

  1. Taking daily photos. I have a hard enough time remembering to take regular photos of my children, let alone a picture of me wearing the same dress every single day. What helped this was setting an alarm for the same time every day. Same days I still forgot and after lying in bed for a few minutes at the end of the night, I would pop up and throw my dress back on for a picture that I had definitely forgotten to take that day.
  2. Static cling. Me-oh-my the static cling was awful. I’ve worn my wool dress all year round and winter is just super dry by me. Most days I would try rubbing lotion on my leggings under my dress to see if that helped. Other suggestions said adding a few safety pins to the inside hem of the dress (that didn’t work). I ended up using a half slip in the colder months whenever I was out in public just to get away from the static. I should have invested in a $5 bottle of static guard. Hindsight, ya know?
  3. Wondering if other people noticed (at first). This struggle went away fairly quickly, but at first I wasn’t going to tell anyone I was doing the challenge. When I saw another mom at Pre-K drop off eyeing the same dress I had worn the last 5 times I saw her, I figured I should let some people in on it. I told my students that I would be seeing most days a week and obviously my family knew along with some close friends. After I told a few people about it, that nagging what if didn’t bother me anymore.

After the challenge

Once my 100 Day Dress journey was over, I did make some changes.  I cleaned out my closet drastically.  I vowed to only keep clothes in my closet that I legitimately LOVE wearing.  Now that I know I can get by with less, I don’t feel the need to keep things for “just in case”.  

Another lasting benefit has been creating a daily uniform. This experiment really made me understand how much I hate thinking about what I wear.  The more routine I can keep things, the happier I am.  My current daily uniform is leggings, a t-shirt, and a chunky wool sweater (it’s cold!).  I still incorporate my Wool& dress at least once a week. When it was a little nicer out, I rotated between a Wool& dress, a romper, and athleisure wear.  This obviously changes seasonally.  

I’m pickier with my clothing. I look for higher quality and sustainable materials now, I prefer to shop second hand, and I make things whenever I can.  All this is the culture of my closet and helps influence my style.  I don’t think I would have taken a hard core reflection if it wasn’t for the 100 Day Dress Challenge. 


It’s also important to note the high resale value of quality clothing.  Facebook is also home to a community of Wool& Buy/Sell/Trade.  The community is active, knowledgeable on wool clothing, and another great resource to have in your back pocket.  I purchased a dress from the Buy/Sell/Trade group.  When I lost the last 15 lbs of baby weight, I resold it for the same price I purchased it at.  Resale is a great way to keep high quality pieces in your wardrobe without breaking the bank. 

If 100 Days is too much…

I know, I know.  All I’ve done is sing the praises of wearing the same piece of clothing for 100 days.  BUT Wool& also has other challenges regularly, including a 30 day challenge.  You could also do your own challenge to be more mindful of your clothing, clear out your closet, or reduce your laundry.  

So, do you think you could do it?  Could you wear the same dress for 100 Days?  I’d love to hear your thoughts!  Leave me a comment below. 

And again, if you choose to purchase something, please use my referral link here!

For more fashion-related posts, check these out:

Minimalism and Fashion: How to Embrace a Wardrobe with Less
How to Curate and Eco-Friendly Capsule Wardrobe
How to Shop for Sustainable Clothing on Amazon
How to Sort Out Fast Fashion Vs Slow Fashion
How to Create a Daily Uniform and Save Your Sanity
How to Shop at a Thrift Store: 8 Essential Tips