I’ve worn the dress two days in a row now for the 100 Day Dress Challenge, and the dress hasn’t grown on me. I think I could wear a dress that I loved for 100 days straight with lots of different style options. But this cut makes me fee like I’m walking around in an oversized garbage bag, albeit an ethically made, fair-trade, non-plastic one. Even with waist cinched, I don’t like how it looks. And when I tried wearing it with an oversized pullover over it (not wrapped like in the photo), I looked like a walking rectangle.

After loudly announcing my intent to complete this challenge, I don’t want to quit. But maybe I should cut my losses and return the dress, or at least stop wearing it. That’s one crucial component of the challenge I overlooked: You have to like the dress.
I am doing the Wool& (Wooland) dress challenge because it’s a promotion they run. After you complete it, you get a $100 gift card – not to mention promoting sustainability and the brand – and I’m enthused about both of those greener points.
Out of all the Wooland dresses, I thought this loose, boxy cut was the one I could “make work” the best.
I could have just challenged myself to wear a different dress for 100 days straight. Something I already own, or something gorgeous and high-end from Frame.
But this is the dress I have, and I’m going to try and stick it out. I’ve read posts from other bloggers doing the 100 day dress challenge. They all seem so much more upbeat about it. One mom from Tennessee confesses she has had her “down moments” with the challenge but wants to spread encouragement and positivity and not air her dirty laundry.
Maybe I am too negative in broadcasting my challenge woes. But maybe other people are struggling too – with the 100 day wool dress challenge or with sustainability. Maybe you’re wondering, in awe, how I can be saintly enough to do this. I’m not. It’s hard. It doesn’t feel good or creative or selfless.
All my worst impulses come bubbling up to the surface. Every other person who’s done the 100 day dress challenges, gushes about how amazing it was. How fun! How easy! How rewarding!
I guess I’m the odd asshole out.
Last night I even went online look for garments I can wear to more or less cover this dress so I can still wear it everyday for the challenge, but I didn’t follow through. Instead, I went to the Goodwill this morning in my dress and tried on several dozen blazers and sweaters and tops looking for ways I can style (translation: disguise) this dress into something I love.
I found no magical cardigan. I tried on one disappointment after another including lots of granola crunchy brands (i.e. REI) in earth colors, and ended up leaving with a few options from the two-hour stack of clothes.
I think I like the pullover and blazer I selected. If I still know what I like? I just know what I’m supposed to like – and that what I am supposed to like isn’t what I like. (And I don’t like the extreme privilege that comes with bellyaching over my not-even-a-real-problem dilemma.)
I know that I have progressive, hippy-dippy beliefs and that I care about climate change and bonfires and the planet. I like organic food and bike riding and book-reading and canoeing. But I don’t like capsulized wardrobes or granola fashion.
Hence my true sentence today: I love the Earth, but I don’t know if I can crunch for it.