I’ve worn the same wool, purple dress for 33 days in a row now. Only 67 more days to go: I’ve made it through one-third of the challenge!

I haven’t been posting daily, or even every few days, as I thought I would at the start of the challenge. Hence a 9-photo collage. (Days 28 and 29 are almost identical but not quite. On Day 28, I wore a black skirt with the ensemble.)


TBH, the dress hasn’t been as much top of mind. It used to occupy most of my waking thoughts. This dress I have to wear. How to style it, what to do with it, and how to get through 100 days of wearing the same garment.
But now I’m so used to wearing it, it feels like an extension of me. I don’t think of it that much. Mostly, I figure out what I want to wear with it when I get up instead of planning it the night before.
On a few days, I changed out of my dress to put on jeans and a tee at the end of the day. I wanted to feel a textural change. The occasional feel of jeans and a simple short-sleeve tee has never felt more amazing.
What I’m Wearing with the Clara Dress
Pictured
- White Cotton Knit Banana Republic Sweater (Purchased used for around $5 from Goodwill. This organic, white cotton knit sweater from Ten Tree is similar.)
- Black A-Line Flare Skirt (TJ Maxx clearance purchase 8 years ago)
- Madewell Tan Twill Pants (Exact style is no longer sold in stores but there are other similar straight-leg pant styles)
- Missoni Wool Scarf (Got it used on ThredUp for a song and I’m obsessed with it. So soft and warm. I’ve worn it as a scarf over my head and a shawl too.)
- Black Boyfriend Cardigan (Purchased wool-cotton blend cardigan secondhand on ThredUp for around $10. Similar style sold black oversized cardigan sold by Everlane.)
- Top Shop Grey Cotton-Poly Blend Oversized Blazer (Purchased from juniors at Nordstrom 5 years ago. You can find an oversized tweed blazer from Vetta with a similar style vibe.)
- 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.
- Amazon Vintage Stretch Belt
Not Pictured
- Grey Convertible Tee
- Ivory Knit Sweater Tank (The closest style that Madewell has now.)
- Hugo Boss Wool Skirt (I scored at a thrift store a couple of years ago for $10!)
- Lifestride Black Suki Pumps (They come in wide sizes for my “D” width foot. I got mine a few years ago.)
- Banana Republic High-Waist Balloon Jeans
- J Crew Sweater Blazer in Oatmeal (Similar style to the item I bought a year ago.)
- Uniqlo Grey V-Neck Jumpsuit (Similar style to the jumpsuit I got 8 years ago. TBH, I like the V-neck one that’s out now even better.)
- Grey Chunky Sweater This sweater is similar to the $5.99 find I scored at Goodwill.
- 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.)
- Frank and Oak Button-Down I got mine used for $5 or $6 but it’s similar to the Kapok Utility Blouse in the link.
- Leather Vest-Harness
- Amazon Vintage Stretch Belt
Dress Challenge Insights One-Third of the Way Through
- With cooler fall weather, the dress is more enjoyable to wear. It’s not hot or sweaty, but it is a 100% wool shirt dress. It’s not a summer midi dress or t-shirt dress. It feels better suited to fall, winter, and spring weather than hot and humid Minnesota summer.
- Even if the brand isn’t 100% sustainable, I’m become more sustainable-minded through participating in the challenge and this is a major win for me. I had an interesting exchange on the October Dress Project page on Facebook (for those wearing the same dress, any brand, every day for the month of October). A few other women said asking critical questions about a sustainable or sustainably marketed brand could be worshipping the green cult movement and I was perhaps agonizing too much over every little detail. Maybe I am. But I think it’s important to be a critical consumer and ask questions and not make assumptions based on the type of product sold or its “green marketing”. What is greenwashing anyway? Am I greenwashed? Is not asking questions being greenwashed? I don’t know.)
- I’m taking better care of myself. While many 100-day challenge participants are liberated from worrying about how they look, for me it’s the opposite. I feel motivated to get put together every day and it puts a swagger in my step. When I’m wearing a lovely, wool dress, I don’t want to shuffle out the door in my Covid-mom uniform of a messy bun, smeared glasses, and ratty flip-flops. I’m taking the time to style my hair every morning, put on concealer and lip gloss, and match my outfit to some other rescued pair of long-abandoned shoes. It takes 10-15 minutes to put myself together in a way where I feel really good. Self-care is different for different people and for me, the ritual of getting dressed so I feel confident every morning fits the definition. I don’t want to wait for a special occasion to spend an extra 10 minutes on myself. I look as good as I ever have or will.
- I miss trendy clothes. I realized this a few evenings ago when out for a night on the town for the first time in ages. I was out with my husband, brother-in-law, and girlfriend. We had dinner at a posh, edgy restaurant before seeing a show. The restaurant was full of easy-breezy 20-somethings grazing on happy-hour tapas. I felt dowdy and matronly in my timeless purple wool dress and “smart” scarf in a sea of blazer dresses, chunky knits, and micro mini-skirts.
- And it’s OK to miss trendy clothes. I am still committed to the 100-day dress challenge. I think it’s versatile enough to be styled as trendy or timeless. I miss feeling trendy and confident, but I’m ok with missing that. I don’t want to consume trends that will last one season. Or if I do, I only want to get a couple of limited-time trends that I will get a lot of wear out of. There are other sustainable, stylish brands I might explore like Reformation or Marcella NYC.
- I see the acquisition of more things as the acquisition of clutter, anxiety, and future trash. This frame of mind is almost certainly short-lived and I will ebb in and out of this way of thinking. But it’s the mode I find myself in right now. Other participants say this is related to finding out what’s really important in life and having a renewed sense of purpose. I haven’t reached this level of transcendence yet, but I’ll keep you posted.