What: 100 Day Challenge

When: Oct. 30, 2022 to February 6, 2023

Dress: Rowena (in Canyon Red)


I heard of this challenge via an Instagram ad – so I was suspicious upon first glance. But, then I went down the rabbit hole and read all of Wool&’s posts from how to travel light to how to style a dress for multiple days of wear. I wear mostly wool when I’m doing stuff outdoors – skiing, hiking, rock climbing. I’ve had the same 5 wool shirts for these activities for several years and while my tees have many holes – I keep patching them because they still work! So, it’s safe to say I was already on the ‘wool-train.’ 

And while minimalism appeals to me and I switch out and reassess my closet per each season, a la project 333 and other capsule wardrobe advice – I find that I don’t wear most of my clothes, I have too much, and still end up feel like I have nothing to wear (?!!). Plus, with the possibility of being able to travel internationally or really at all after the past couple of years re-emerges for me – I was feeling uncertain as to how I’d pack to travel around Korea for a whole month next May. So for both of those reasons, this challenge appealed a lot to me! Can I bring one wool dress, jeans, a wool tee, and a jacket to Korea and call it good? Maybe! Can I wear the same thing for 100 days before I go to Korea to test it out? Yeah, probably. So, that’s what I’m going to do from the end of October to February. 

I’m looking forward to simplifying and decreasing decision-fatigue – especially when I have to ‘go out’ of my house (I work from home). I’m never sure what to put on or if my ‘daytime pajamas’ are ok … usually not. I think that wearing the same dress everyday is a good reason to rotate through all the jackets I own and apparently love. And, I already do this with my shoes, as I wear the same shoes everyday (summer: Tevas, winter: Blundstones). I did just upgraded to Thursday boots with a heftier, grippy soles for the icy winters in Bend after wearing my Blundstones for 4 years.

How did it go?

First 50 days (half way point)

It’s been easy to get up everyday and wear the same thing. It’s freed up some energy for me to refocus on morning routines, like walking Tepals, yoga, and journalling. I picked the Rowena Dress, long sleeves, because I knew I wanted to do this challenge during a snowy winter here in Bend, OR. I pair my dress with a sweater or pullover and grey cotton leggings. I do wish I had wool leggings (maybe what’ll I’ll purchased with my gift card!). Instead, I added in a pair of knitted leg warmers.

Surprises or challenges so far:

  • I am surprised I miss wearing pants
  • I do laundry during the day, which can be a challenge when you have only one item to wear. I’ve adjusted to start wash in the evening so my dress can air-dry overnight.
  • While I’ve worn my dress hiking, it’s not the right garment for rock climbing or skiing. So, I’ve missed 4 days already of the 100 day challenge (with total allowable missed days at 5)!

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