The One and Done Challenge

I have a long, long history of jumping into things without looking. Give me five minutes and I’ll agree to travel across the world, adopt your goats, or, as happened on that fateful August day in 1994, agree to teach high school history with no experience or training.

Sometimes it works out. Most of the time I learn a lesson. Pretty much every time I wonder, “What was I thinking?!?”

Inspired by my friends Yana and Sarah, I challenged myself, and my readers, to a week of dresses. Me, bike commuting, goat wrangling, chicken herding me, was going to wear a dress every day.

To be honest, it did not start off well.

Monday morning it was snowing. Not the sticking-on-the-ground-no-school sort of snow, but wet, slushy cold snowing. I put on a dress, and just kept going. Leggings, boots, jacket: By the time I was finished you could barely see the dress. My day went just fine, but I skipped the bike commute (did I mention it was snowing?) When I arrived at the rock climbing gym, as is my habit on Mondays, I found I’d forgotten by climbing kit. Ordinarily I could have borrowed a pair of shoes, but there is no way I could climb in a dress.

I found there is very little I couldn’t put on over this black, shirt-waist dress.

 

By Tuesday things were looking up. I wore an olive linen dress with my beloved denim jacket and old Spanish boots. I felt like I had stepped up my work ensemble, but was fantastically comfortable due to the jacket and boots which always give me confidence.

You make everything better, denim jacket.

 

Wednesday I paired a sleeveless, summer denim shift dress (My grandma would have loved this! Grandma’s lessons for effortless style) with a chartreuse sweater, and my Frye boots. This didn’t even feel like wearing a dress. Some hard-core rain gear got me to school warm and dry, and this time I did not forget my climbing kit and had a great time at the gym falling off all sorts of routes.

Photographs taken at 6:25 a.m. are not my favorite things.

Thursday was the fancy day. This dress does not photograph particularly well, but it is fantastically flattering. One student stopped me in the hall and said, “Ms Grace! I’ve never seen you wear a dress before!!!” Never mind the fact that’s I’d been wearing dresses all week…

I found this on Stylewe, a site I can waste hours and hour on…
This detail gives you a better sense of the dress.

Friday was sunny, the first time our valley had seen the sun in nearly 2 months. I fell back on an old favorite, a denim dress I wore regularly in the fall. By this point in the week I was feeling much more confident. Then I changed into jeans to go out with friends after work.

Again with the old Spanish boots! We had a fun week.

On Saturday and Sunday, I didn’t wear a dress, because I went rock climbing with my husband at Smith Rock, and even I know when to cut off my cock-eyed experiments before they go too far.

Not a dress.

What I learned in five days of dresses:

All my dresses look alike

Seriously. I own 7 casual, work-appropriate dresses. Five of them are blue, one is black and one is olive. Five are button down, shirt-waist dresses. All but two are denim or denim-like.

One is plenty.

This speaks to bad shopping habits. One casual, blue, button down denim dress, great. But I should not be buying every other casual, blue denim dress I come across. Wearing them all in one week drove home the point pretty clearly.

It really does help to have options.

Wearing a dress every day for five days meant I had to wear almost every dress I own. Both Yana and Sarah advocated dress wardrobes of abundance. By Friday I didn’t have much choice and I didn’t feel like some Zen minimalist freed from the weight of consumption. I felt like I needed a trip to Buffalo Exchange, stat.

Shall I wear the blue dress or the blue dress?

I am not a master

Sarah and Yana made adding sweaters and jackets and boots sound easy, and to them it is. But I have a lot to learn about how to style dresses. I’m excited to try again, but I’m going to wait until the heat of late July to try for a full seven days. I hope you will join me for a summer One and Done challenge.

OK, so I have gone rock climbing in a dress. But only once.

Did you try a week of daily dresses? How did it go? Let me know in the comments below.

 

 

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