100 Day Dress Challenge

Say it Rah-shay By Jan 21, 2021 1 Comment

Y’all know I just cannot resist a challenge and here is another one!

When Covid first hit, my friend Becky shared photos from a dress challenge she was doing in which she wore the same dress from a company called Wool & for 100 days. I wore Becky’s DMs out asking questions about the dress. Was the dress hot? Could she wash it? Did she wear it when it was cold? Was it comfortable and so on and so forth. I would peep the Instagram hashtag and kept my eye on the dress because each time I was ready to order, it would be out of stock. I considered the challenge using a dress I already owned but the holidays came, the pay gods worked in my fortune and I was able to gift myself a Rowena Swing Dress. 

I’m about a quarter of the way through and it’s been a bit of a challenge in ways I did not even imagine.


First, the dress. Ro, full name Rowena Swing Dress, is, well, a swing dress. From the blog Cecelisa.com a swing dress is defined as

A modern swing dress is a flowy dress that still has an A-line shape. Instead of the top part of the “A” shape hugging your waist, it often will hug your chest and then the fabric will bell out from there. This gives the dress lots of movement potential…. the dress will “swing” when you walk or dance!

And yo… Ro IS swingy. It swishes as I walk, flutters as I go about my day, is very forgiving on those days when I am feeling bloated. However, this same swing that I find forgiving can be somewhat shapeless and sometimes I feel that the shapelessness can be a bit frumpy. 

There are other styles of dresses available but I went with the Rowena because I thought that was the one that would allow the most versatility, would be best to complete the challenge without my coworkers realizing that I was wearing the same dress daily.

The price of this dress almost made me gag. I am a thrift shopper. Mostly because I hate the whole act of shopping (childhood trauma is a trip) and because I get flashbacks to my heavier days. Why are clothes for women of a certain age or size so damn frumpy? And where is the rest of my shirt?

I probably should have gotten a medium instead of the large. I went back and forth trying to decide on sizing and settled for large. My clothing size has changed a bit in the last year but there is still a part of me that does not trust that the medium sized clothing will actually fit. Also, my eagerness to start the challenge allowed me to fool myself into thinking that the sizing was ok and I would work with what I got but no no no. There are days when the dress just feels like so much fabric. More on this in a bit.

Styling the dress

Even a casual glance through the hashtag will show that people participating in this challenge are not here to play. Their photos are beautiful and creative, with participants showing off bits of their lifestyles and the creativity that people have styling their dress. 

I found myself getting caught up with what I would pair Ro with instead of just wearing the dress. The Bee and I would hit up thrift stores or dig up those sweaters that we hadn’t wore in a while in an attempt to accessorize. I was talking with my sister about the challenge and she asked why I was making it so hard and I had to admit that I was forgetting all about the reason for the challenge. 

Some of the ideas behind the challenge from the Wool & site include: 

  • Spend less time and money doing laundry and dry cleaning (duh!).
    One lady claimed that she only washed her dress four, FOUR!, times. I’m not down with that. I’m all for wearing something a few times between washes but working in a dusty library, going about my day to day life as well as COVID makes me want to wash my dress a bit more frequently. Also? Since the dress is a little big on me, I feel that after several wears the dress is just hanging, even more shapelessly, on me. 

  • Learn how to get more wears out of a garment (e.g. when you spill on your dress, you’ll immediately take action to clean it since you’re wearing it again tomorrow!).
    I am extra careful about spills and such. Laundry is a pain on its own. The idea of washing this dress daily…bah! Our dryer has a refresh option so I get a break there. 

  • Recognize what you need and don’t need in your wardrobe.
    This is still a work on progress as so far I have been using the same sweaters and scarves that I would have worn pre-challenge. I have slowly begun to go through my closet to purge a few items that would be ignored as I got dressed in the morning. There is nothing wrong with them; it’s just time to let some pieces go. 

  • Have more money to spend on experiences with the people that make you the happiest.
    Since the majority of my clothes are thrifted or from the sales rack (yes; I am a cheap so and so) I wasn’t spending that much on clothes anyway but I am a bit of an impulse shopper. I will spend money on things that I do not need just because it is inexpensive. 

  • Reduce your impact on the planet when you realize you don’t need a closet packed full of clothing.
    Watching Hoarders on A&E has made me reconsider needs versus wants. It feels almost criminal watching just how much stuff is thrown out each episode and I have been trying to reduce the amount of clutter in my space. It is kind of stressful to see piles of junk all over.

Casual wear has been a challenge. Because the dress is so loose, I have trouble tucking it into my jeans and and I have not quite embraced the trend of tying it into a knot or bow. It works well on other wearers but not so on me. 

Looking through photos I notice I wear a LOT of dark colors. 

What’s next?

Want to see more of my challenge? Pop on over to Instagram and follow me there. I’m @sayitrahshay. If you want to see how people are styling their dresses, check out the 100 Day Dress Challenge Hashtag.

Share your fashion tips in the comments here on IG. 

I’ll be back with an update when I hit the halfway mark

Swishing and swinging,


I am mom, daughter, sister, yarn lover, word lover, crazy cat lady and library chick. Find me with book or with hook and a hot cuppa.

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