Days 10, 11, 12, 13, 14, 15 of 100 Day Dress Challenge

I’ve now worn my wool dress from Wool& (Wooland) for 15 days in a row. Only 85 more days to go. (Related read: What is the 100 Day Dress Challenge?)

Clara Dress for 100 Day Dress Challenge

I haven’t shared an update in a few days, so I’m combining a handful of days into one collage image and post. For Day 14, I shared two pics; one with and without my wool blazer cardigan from J. Crew. (I purchased it this spring and it’s become a wardrobe staple I love.)

Day 10 outfit: Vetta t-shirt (the softest tee I’ve owned and you can wear it cropped or draped) with white leather platform Soludos sneakers. (Shop Soludos Ibiza sneakers and Vetta convertible tee.)

Day 11 outfit: Target necklace and velvet midi skirt from Nordstrom juniors department. I purchased it several years ago and had only worn it a few times.

Day 12 outfit: Banana Republic silk button-down shirt with the dress worn as a skirt. The shirt is tucked into the Clara dress belt. I got the silk shirt on clearance at Banana Republic (for $9) I don’t know when. Glad I finally cut the tags and wore it. (Banana Republic shirt no longer sells but you can shop this similar style Banana Republic silk blouse.)

Day 13 outfit: Black 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

Day 14 outfit: Wool cardigan blazer from J Crew and Lotta from Stockholm leather clogs. They are a made in Sweden brand that I got used online. The clogs may be neither trendy nor classic, but I love them so much. (Shop Lotta from Stockholm clogs on Amazon. I bought the J Crew sweater blazer on clearance a while ago but there’s a similar style you can buy on

Day 15 outfit: Stretch leather belt from Anthropologie and Nisolo black leather Chelsea boots bought used from Mercari. (Shop Chelsea Everyday Commuter boots on Nisolo. There are a few Chelsea styles and I think mine are the Commuters – as I bought them used I can’t be sure.) I love that Nisolo has ethically and sustainably made goods, but it’s priced out of my budget. I may set some alerts on Mercari though to be notified whenever the brand gets listed in my size.)

I’m into it

I’ve definitely found my groove when it comes to this challenge. I was initially discouraged because I didn’t see the Clara Wooland dress styled in a way that resonates with my aesthetic. Lots of women pair it with varying scarves, ascots, dusters, and shawls. I don’t wear any of those items. I had never seen the Clara worn with a blazer and updo, or as a skirt, or as a shirt. I’m having fun changing it up.

Turns out I’m not allergic to ironing or going to the drycleaners

I have ironed this dress three times. I’m ironing my clothes for the first time, well, ever. I had used an iron here and there before in my life, but honestly, it had been over a decade. (In my defense, I’ve had casual work environments and I used to own a steamer.) I’ve discovered it’s satisfying to take an iron to a wrinkle.

I’ve also brought and picked up garments (not the dress) from the dry cleaners for the first time in over a decade. This challenge has made me slow down my fashion choices and take pride in and better care of the clothing I do own. I got dry cleaned: my wool sweater blazer, my black blazer, and a short sleeve knit top.

Similarly, I’ve spray-treated all my leather shoes for the first time in an embarrassing number of years. I had leather spray in the closet. And good intentions. They finally converged.

Big picture, big details

Accessories are playing a bigger role in my wardrobe now. I’ve always liked clothes but (oddly) not been as into accessories. It’s to do with me being more of a big-picture gal and not into the nitty gritty. But accessories have an elevated role when wearing the same dress each day. I find myself enjoying the process of picking out belts, earrings, and necklaces. There’s more emphasis I am putting into details – in fashion and beyond.


And for family photos tonight, I wore my Wooland Clara dress! I had thought about wearing something else. (Technically, I only have to wear the dress 6 hours a day for the challenge.) But I decided to just go for it. Margot wore her Wool& dress too.

She explained to the photographer we were doing the dress challenge “So my mom can win. She likes winning.”

Margot is not entirely wrong. And the truth is always a good look for someone to wear every day, right?

Just stop me when I get to 100.

My 100 Day Dress Challenge

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