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

We Tried It 18

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

clothes, cold weather


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the4m... the4mutts

I wear dresses & skirts in the winter constantly. No big. But those all (imo) look horrid on you. It looks like you shopped in your 70yr old grandmothers closet.

This look can work, if you wear more updated clothing, and less frumpy sweaters over them. The first one was the only one that looked halfway decent to me.

nonmember avatar CrystalMP

I love the look for day four!

nonmember avatar Jess

Eww @ the first comment. Some people really don't understand the ” if you have nothing nice to say...don't say a thing!” rule. I think you looked cute :) it looks comfy, I think I should be challenging myself too!

ZsMommy ZsMommy

I worked retail for 20 years in a cold state-Black HUE tights and mini skirts on the coldest days-yup-no problem. Heck-tights are even better than pants cuz they are close to the skin and don't let the cold air circulate past your skin.

OoOJa... OoOJanisOoO

I really liked the 4th one. I love wearing dresses but I am so picky. It is so hard to find a dress that is not too short, has sleeves, is a color or pattern I like and is in my price range. 

nikki... nikkivolkov

Boo 4mutts. I think you look great. :)

linzemae linzemae

I don't even wear dresses in the summer. Too chubby for that!

nonmember avatar melissa

Wow 4mutts that was really blunt and obviously taken offensively by others.

I have to say that I think you could find even better dresses but that's my style vs yours. I don't know you so maybe this is you. Maybe the hair being up would allow me to see the cut better - it is just a picture!

I get what your saying though -mix it up layer etc. and you should be able to write piece without people smashing you but.. welcome to the internet!

bella... bellacazzate

Damn, Mutts!

I am from the magical land that is Boston and I manage to wear a dress everyday without fail. Neither snow nor rain nor heat nor gloom of night stays this dress connoisseur from the swift completion of a... day without dreses? Sorry, the comparison began to get lost. Anyway, it's not because my dress-wearing skills are superior; it's because my legs are terribly short and finding a pair of pants that doesn't drag and get destroyed during the winter is impossible. Also, I kind of hate pants.

Fleece lined tights are key! And sweaters and cardigans and scarves!

the4m... the4mutts

I am not really concerned by whether or not anyone took offense to it. I said they look horrid on her. I didnt say shes some hideous fucking chud or something.

Its my opinion, and in my opinion, its true.

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