Day 2 of 100 Day Dress Challenge

I’ve made it through day 2 of the wool dress challenge even though it’s only 3:30 pm. I’ve worn the dress for nearly 8 hours today, and the requirement is 6 hours. I could immediately go change, but it feels like that goes against the spirit of the challenge. I probably will later this evening when I go on a bike ride.

The challenge has had some pros and cons today.


  • I didn’t have to worry about what I was going to wear today – especially great since I had to get up early and bring Margot to her first ice skating lesson (group session) at the Rec Center.
  • Margot is excited to be doing the challenge with me. For her, it’s day no. 2 in her wool twirly dress.
  • It’s a comfortable fabric to wear.
  • With the dress my outfit’s VIP, I am changing up my shoe game. I’ve worn 2 different style wedge booties today that I had not worn in eons. The challenge is prompting me to reevaluate and re-wear a lot of my wardrobe that had lain dormant.


  • I am still having a hard time embracing the dress’ loose cut and non-trendy style. It’s nightshirt (oversized T-shirt) length and there is no defined waist. Even with the tie cinching the waist, it makes the skirt bell out in a weird and unflattering way. I may take in the waist a couple of inches, or get some double-sided fabric tape to give this dress more variety.
  • It’s not as classic and go-with-everything as black. Hindsight.

I did buy a handful of nice pieces at the Goodwill to coordinate with this dress. For just under $25, I bought a wool knit sweater, grey organic cotton knit sweater, and a black Brooklinen blazer (that should go for $500+ on the Brooklinen website).

Although I was tempted to buy a pair of almost new cognac brown leather sneakers that were a perfect magic fit, I passed. They just didn’t spark joy the same way the thought of a new pair of white leather sneakers does. Going capsule all season, I am going to indulge in this trend.

I was also tempted to bypass Goodwill and just buy some brand-new coordinating pieces online. (After 2 years of work from home and a casual dress code now, I don’t own cardigans or blazers.) Frame speaks my language and sends me texts (sigh). But right now, I am trying to make it through the challenge one day at a time. After I’ve made more progress, I may feel more inclined to invest $200 in an ethically made, fair trade, wool pullover. But by the time I make enough progress on the 100 Day Wool Dress Challenge to “merit” one, I may feel that I don’t need it.


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