Days 34, 35, 36, 37, 38, 49, 40, 41, 42, 43, 44, and 45

100 Day Dress Challenge: Made it to 45 in the Clara Dress

I’ve now worn the same dress for 45 days straight. Only 55 more days to go to complete the 100 day dress challenge.

It’s been 12 days since I last posted my progress and reflections on this dress challenge.

I’m struggling. Not with the dress challenge itself, but with life challenges in general. Just your run-of-the-mill crises related to family-job-career and general life existence. I’m grappling with how to have a purpose-centered identity and major general anxiety.

For the first time, my clothing cannot reflect my state of emotional disarray.

I can’t move throughout the day in a t-shirt, jeans, and tangled hair shoved into a sloppy bun.

I have to wear this purple wool dress every day for the challenge. And take a picture. This means at the very least I have to steam out the dress’ wrinkles and comb my hair.

While I have worn the same dress every day, it’s been in a more minimal way. Shoving on the dress. Putting myself “together” for a picture. And then shedding the layers: skirt, shoes, blazer, and other accompanying garments. It has struck me as vain and pointless. It feels worse than fake: it feels contrived.

If I didn’t have to present myself a certain way every day, and just sink into pajama pants and faded tees, I wonder if I would feel better. Because my outfit would be congruous with my state of mind. I’m not sure.

But I’m still wearing the same dress every day. I’m well past the 30-day marker, so it’s onward to 100 days.

What I’m Wearing with the Clara Dress


  • Striped Tory Burch skirt in navy, white, and periwinkle. The skirt is a thrift store score from 5 or 6 years ago. I’ve only ever worn it twice though, and both times were with this Clara dress. Down ther road, I may invest in another Tory Burch midi skirt. The fit and quality are great.
  • Over-the-Knee Leather Boots (I am seeing these priced everywhere around the $100 mark but I got them for $38.99 somehow. Maybe it’s a discontinued color. I had been wanting to pull the trigger on leather knee highs for a couple of years and the stars aligned.)
  • Old Navy High Cropped Workwear Jeans in Petite (There is Regular and Tall Inseam too. The style is not stretchy, so I sized up.)
  • Banana Republic Hayden Taper Pants in Light Heather Grey (Stretch waist for the win!)
  • Nisolo Black Chelsea Boots (I found these used on Mercari.)
  • Lotta From Stockholm Clogs It’s a Sweden-made brand but you can find them sold on Amazon and resale sites.
  • White Platform Sneakers Soludos brand sneakers. The style name is Ibiza.
  • Taupe wool sweater (used from thredUP)
  • Madewell linen cotton blazer in dusty mauve (purchased on clearance several months ago)
  • Black Boyfriend Cardigan (Purchased wool-cotton blend cardigan secondhand on ThredUp for around $10. Similar style sold black oversized cardigan sold by Everlane.)
  • Toad & Co wool duster/long open-front sweater (Purchased 3 or 4 years ago)
  • Black lined Brookline blazer from Goodwill. I got it for $6.99 and paid $11 to have it dry-cleaned. (I did some digging and found a link for this Brookline blazer new on
  • Baby alpaca wool cropped cardigan in charcoal gray. (I wrote an article about the brand One Quince. The brand promises sustainable, ethically made clothing at affordable (fast fashion) prices. I didn’t know if those claims about ethical, sustainable production were true, and wanted to see and touch the quality first-hand. Read the One Quince review.)
  • Grey baseball hat from Tentree (I wrote a review of Tentree and wanted to try out a couple of products as a consumer. I wasn’t paid by Tentree. I paid for the hat and love it more than I would have thought possible.)

Not Pictured

My 100 Day Dress Challenge

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