Finished: 100 Day Dress Challenge

My 100 Day Dress Challenge is finished. My 100 days were August 19 – November 27, 2021.

It was easier than I expected. No mooning, playground or underwear incidents.

I was not as creative as I expected. I did not bust out all my jewelry or change much daily.

The dress held up way better than I expected; I’m hard on clothes. I have no tears, holes or snags.

I washed it more than I expected (once or twice a week) and always because of armpit area smell, never for general odor, stains, etc.

It’s super kid friendly: peanut butter, chalk, bubbles, and play dough all come off beautifully.

I’m not much better at selfies, but I learned how to contort for pictures and how to use my phone’s timer. A reminder that I’m only 5’1″ and my husband wasn’t really into being a photographer. I also don’t have a phone stand or fancy setup. I did not figure out a good spot for lighting for full body pictures to show off leggings, but I was usually able to show a good amount of my dress.

My layers didn’t happen the way I expected I was thinking all my cardigans, including my long cardigans would look great, that leggings would work wonderfully, and that I could layer shirts and skirts over my dress. Shorter jackets and cardigans looked good to me, but I thought my longer sweater jackets made me look bulky. The pockets didn’t work well with me trying to tuck my dress into my jean skirts, there was too much going on around my waist and I don’t have a small waist to begin with. Layering shirts over my dress were not always flattering but I really loved how shirts looked under my dress, even my husband commented how nice they looked underneath and he does not comment on clothes. All of these reflections are my opinion and not the opinion of others, no one shared thoughts on my individual outfits except as I mentioned my husband liked when I layered tops underneath the dress. I will say that near the end layering was more to add a splash of variety or try out an idea. I got over how it looked and if it was just comfortable.

As I mentioned, I wasn’t in love with how my leggings looked with the dress. There wasn’t any bulky issues with the waist band or static, honestly it just didn’t seem “as cool” as I expected. The weight and protection from cold were fine, but I didn’t feel particularly attractive seeing the legging photos. I loved layering my thin swingy black and white skirt under my black dress and I did that a lot, it’s the first picture in the collage above. I would put a jacket or cardigan over my dress and skirt and it was one of my go-to looks when it was a bit cooler or I was going to be in a doctor’s office, which are always cold. I did stick more with my red and black color scheme as mentioned previously which I think helped with the looks. My navy pieces, which I have a lot of too, were always a bit quirky to me on top of the black. It wasn’t off but it wasn’t as cohesive as I thought.


  • Wool holds up so well. If I had done this challenge with cotton or a cotton-poly blend, the piece would not have lasted between pilling, ripping, or whatever. I can’t even keep a cotton-poly shirt for two weeks without this happening so I definitely will be looking for more sustainable fabric items in the future like wool and bamboo.
  • This did end up reaffirming my minimalist approach to possessions, especially clothes. I pretty much rotated through the same few pieces. I ended up re-homing more wardrobe pieces and jewelry, which surprised me because I don’t have that much relatively speaking to begin with but I was able to get rid of more. Pieces I didn’t use in the challenge and honestly had not worn in a while moved on. Polyester pieces that were pilling and tearing were “recycled” if I wasn’t comfortable donating them, but please remember that polyester and cotton-poly blends are almost impossible to reuse (they don’t absorb well as rags for example) and don’t “recycle” easily (because of the blending) so try to avoid even bringing those pieces into your home or “justifying” vendors continuing to make and offer those options.
  • Though I tended to wear the same thing most days as it was hot for most of my challenge, this was fun for me. I did wear more variety of my jewelry than previous to the challenge and I worked with color coordinating more. Several of my new favorite pictures of myself are from this challenge and I have a few new favorite outfits that can be go to outfits.
  • This dress, in my opinion, looks amazing on Zoom. I did not rearrange necklines or fidget when I wore this dress on a Zoom call like I do with other outfits so I guess that means I also felt really confident in it. How this works out in real life for you could be really eye-opening as it was for me.
  • Layering may not work out the way you expect. Theoretically one of the reasons you may be doing the challenge is to get away from clothes defining you, being hung up on image, or having a lot of variety. I think of the scripture verse Matthew 6:25 on this topic, “Therefore I tell you, do not worry¬†about your life, what you will eat or drink; or about your body, what you will wear. Is not life more than food, and the body more than clothes?” The challenge did help me let go of thinking about how I thought I looked in an outfit or how others may think I looked in it. Feeling/comfortableness is another matter, but the how I thought I looked or how others may think I look, I was definitely able to move away from that more so I’m pleased with that growth.
  • Take a picture first thing so you don’t forget. Take better, funnier, crazier ones throughout the day but just make sure you have one. You can always delete but never add. Remember you can miss 5 of the 100 days and still qualify for the coupon.

When you submit your photos for the challenge as part of the review to get awarded your $100 coupon for a new dress, wool& includes a survey. They asked me what was my biggest takeaway from the challenge. When I responded to them I said it was that no one cares what you’re wearing. That seems true so I’m still okay with that answer. However, in reflecting on that answer to write this post I am going to completely change my answer, especially after going through several days post-dress-challenge. My biggest takeaway is the de-stress/lack of stress about what to wear. This includes making a decision, see if the outfit fits still, and do I feel comfortable enough to wear the outfit all day. Since having a child, those three things are part of all outfit decisions in the morning except during the dress challenge. My inherent body structure, with broad shoulders and thicker thighs, and a post-baby tummy have made clothes shopping annoying. Having the dress-challenge time away from all that was so enlightening. I will probably include my dress more in my outfit options going forward, and it will again by my go-to when the warm weather returns.

I submitted my finished challenge photos link to wool& and actually received my coupon code the same day. That may not be typical but I wanted to share that awesome customer experience. I chose for my “reward” dress the Willow Swing Dress Long in Plum. My size and color were in stock, that doesn’t always happen as the challenge is very popular, and it shipped the same day I ordered it. As a reminder though I am petite, I like to have my knees covered so I ordered the long length like I did with my Sierra Tank Dress in Black. If you have been following my story on this, please know that wool& has added several new styles of dresses and many new colors to their original line up. I recommend you check them out! Don’t forget that wool& has a kids challenge and the men’s shirt version is at Wool & Prince.

If you have been inspired to try the wool& challenge yourself, or try or design a similar concept challenge, please share you experiences and biggest takeaways.

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