100 Day Dress Challenge

Coming into the fall last year, I decided that one of my goals is to curate my closet and make some updates so it better reflects my style, fabric preferences, and color profile. To that end, I had been reading through my copy of The Curated Closet and researching some ideas on Pinterest. From there, I came across an ad for the Wool& 100 Day Dress Challenge. I had mentioned it to my husband in passing, and then I came across it again at Christmastime. My husband had a gift card and said, “I’m going to order you a dress for that challenge.” He’s an activator. 🙂 So I picked out the Bristol Dress in the color Thyme. It is a sage green with ivory stripes. I knew I didn’t want to use a black dress because I have been trying to step outside of black. I also liked that it was a different style of dress than my typical shift dress, and I thought it would layer decently well.

The dress arrived very quickly, and I started the challenge on December 31. It was all a very quick turn-around time from deciding on the dress to starting the challenge. This was probably best because I am a very particular, analytical person, and I would have agonized over ‘the best way’ to make the challenge successful (i.e. picking out shoes and tights/leggings and sweaters to buy and use with the dress). It was better for me that I just started and then had to figure a few things out as I went.

Here’s how it turned out—

The first few days were easy. I was feeling good about the challenge, and my desire to ‘conquer’ the challenge was definitely high. I did encounter a couple of frustrations right away, though. First, I had a whole drawer of tights, but I realized that only a couple of pairs fit comfortably or worked well for my needs. It was winter, and I had to have leggings or tights to stay warm. I ended up ordering a pair of navy blue cotton tights from Amazon as well as buying a pair of light gray cashmere leggings from Poshmark. (Later in the challenge I also added a thinner pair of brown leggings, which have been a nice addition.)

The second frustration was shoes. I don’t really mind wearing the same dress over and over again, but I really like having the option to switch up my shoes depending on the look I am going for. As I have been transitioning to barefoot shoes, more and more of my traditional shoes did not fit…or hurt my feet/back. In December I had gotten the Peerko Go Leather Ankle Boot in black, which I’m very happy with, but I wanted a couple other options to round out my wardrobe. I was putting together a list of shoes I’d like to add over time, and my husband ended up surprising me with a few of them. He got me the Dalia Leather Loafers in black and the Shapen Ankle Boots in brown. It was such a nice surprise, and it helped me a lot with the challenge! I also ended up snagging the BeLenka Olivia wool lined Ankle Boot in nutty brown with some credit card points I had from Christmas shopping. They were great for cold and snowy weather.

At the start of the challenge I was really trying to see which sweaters I could make work for layering. Some were more successful than others. The collar on the Bristol dress wasn’t the best for some sweaters. There were definitely some days I didn’t want to wear the dress, but for the most part, I didn’t mind.

Note about Day 19—I woke up and went to put the dress on when I realized it had a big tomato sauce stain down the side. I suspect my 3-year old had something to do with it. 🙂 I tried to spot clean the dress, but I ended up putting it through the wash. It hung dry the rest of the day. I will say, the dress washed up quite well.

100 days seemed so long at the beginning of the challenge, and then suddenly it was only 2 weeks until the end. It’s funny how time slips away like that. I will say that I hit a stretch of the doldrums in the middle of the challenge where I really wanted to throw in the towel. I was just tired of the dress and tired of feeling restricted in my choices. That being said, I took a good hard look around my closet and ended up trying out some new combinations that I ended up really liking. I’m glad I stuck with it and had those discoveries.

So what are my main takeaways, you ask? I have a few.

First, I realized that I really enjoy wearing dresses! I have always liked dresses, but I thought I would get tired of wearing one over and over again. I really didn’t. And the few times I put jeans on during the challenge, I was so uncomfortable! Some people hate tights, but I really don’t. I also realized I prefer the silhouette of a dress over pants. I’m not entirely surprised by this. Dresses flow better over your body and just fit very differently than pants. I struggle with pants hitting too high or too low and the resulting complication of shirt length (to tuck or not to tuck?!). A dress eliminates that conundrum. I also struggle with pants falling down and feeling like I am constantly adjusting myself. I didn’t feel that wearing the dress.

Second, I realized that I totally don’t mind wearing the same thing from Monday through Friday, but I really want to have the option to wear something different on Saturday and Sunday. I think it is partially a delineation of the week from the weekend. Also, Saturday feels more casual or something—like pants and my most comfy shirt/sweater. Typically we dress up for church on Sundays and then I wear that the rest of the day or put on lounge clothes for the afternoon. I didn’t mind wearing a dress on the weekend, but I didn’t want it to be the same dress I wore for the week, and the dress I chose for the challenge didn’t ‘dress up’ very well.

Third, I realized that this style of dress is not my preferred silhouette. I carry weight in my middle, and the more fitted nature of this dress brought up some insecurities in that sense. I had several days where I just wanted to throw on pants and a big sweater rather than ‘face’ myself. It was a very good exercise in trusting the Lord through body image issues. I definitely won’t be stocking my closet with this particular style of dress. That being said, I am glad I chose this dress, and I am glad for the different challenges it brought up for me to walk through.

If I went back in time, I would choose a swing dress for the challenge. I really love that style, and I think it would layer well with a variety of shirts and sweaters. The collared neckline of the Bristol dress did make some sweaters a little difficult, and in general, I don’t go for a polo style top.

Will I continue to wear the Bristol dress after this challenge? Yes! Although it isn’t my most favorite style ever, I do like it, and it is a nice change of pace. I think it is a great addition to my wardrobe—it is comfortable; I like the color and the stripes. I also really like the weight of the wool for this dress. It doesn’t feel heavy, but it is warm. It is not see through, and even though it is long sleeved, it layered very nicely under other sweaters.

My main takeaway as I am thinking through my closet is that I can do with a lot less. I’d like to have a couple of easy dresses with a couple of sweaters for layering different looks. Tights and shoes make for an easy swap of the style/vibe, and scarves are also a nice accessory to change up a look. I’m going to spend some time narrowing down a color palette that I think will help all of my pieces go together a little more seamlessly. As I’m putting away my fall/winter clothes and pulling out my spring/summer clothes, I’m applying these same principles and will be downsizing a lot of my t-shirts and one-off clothing items. It feels good, and I’m excited to see my closet coming together in a way that better fits my needs and style.

I’d love to hear, would you ever do a dress challenge like this?