I Wore a Dress Every Day for a Week in Cold Weather & Almost Failed Miserably

dressOnce the temperature dips below 60 degrees, I wear jeans just about every day. Even when it's warm, my jean wearing stat is probably close to 80 percent of the time. Now that it's winter, it's jeans every day or yoga pants while inside and I am so bored with my clothes choices. So I challenged myself to not wear pants for a week. That meant dresses or skirts even in frigid temps while running after and around with my 3-year-old twins doing my typical stay-at-home mom duties who freelance writes while wearing yoga pants and sweatshirts.

Could it be done? The key was layering.


Day 1: I pulled out a summer dress, wore warm leggings underneath, and put on a sweater. It was almost like a typical day in the yoga pants but with this flowy thing attached. Why didn't I think of this sooner?

Day 2: This summer dress thing is brilliant. I took out that sheer vintage summer dress that I can never wear in actual summer because it's so sheer and layering is annoying when it's really hot and made it work with leggings underneath and a cardigan.

Day 3: I failed. It was raining. Dresses seemed too complicated. Jeans didn't.

Day 4: I took out one of my favorite dresses. One I'd wear to work in the city before I had kids and back when I had a full-time gig. Too much for a day of pickup and drop off at pre-k? Not for this challenge. I put those leggings back to work and wore a tank underneath for extra warmth. Side note: In case you noticed, I got a new bed and hot glued some ribbon to my mirror thanks to my Pinterest addiction.

Day 5: I failed. 

Day 6: The dress I bought in summer with buttons all the way down the front, the one that never stayed buttoned at the chest? Perfect to wear with a sweater and chunky leggings underneath.

Day 7: Since I was feeling adventurous and trying to wear things I never wear, I tried on this vintage dress that looked adorable on the model on Etsy but just felt like a schmatza on me. Or one of those house dresses my grandma used to wear. That's what this became since we didn't leave the house.

Wearing dresses every day took a lot of work. More than I thought. I'm just so used to my jeans or yoga pant go-tos. And while I will not be giving up my pants any time soon, I do feel I can throw in one of my dress options during the week so I'm not as bored and have more choices.

Do you wear pants just about every day? Do you think you could do this challenge in winter?


Image via Michele Zipp

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