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.

 

 

One and Done: The Daily Dress Code

Could you wear a dress everyday? I often look at pictures of women from earlier times and envy them their simple wardrobe of dresses. * Dresses are flattering, and can be fantastically comfortable, but… an all-dress dress code? As it happens, I have two friends who manage to do just that.

And no, these women don’t spend their days in idle relaxation. Sarah Prater is a respected teacher of writing. She’s that English teacher who asked hard things of you and actually got you to do them. Yana Gorskaya is a film editor and writer in LA who has made scores of films including What We Do In the Shadows and Spellbound.** Both women have families, hobbies and sixty billion things to get done in a week. So they’re just like us.

It’s so simple

“I didn’t always just wear dresses, though I have always had a fondness for them.” Yana says, “But a few years ago I put one on and didn’t look back.”

Yana, with adorable dress, boots, daughter.

Discussing dresses with each woman I was struck by just how easy their mornings are. There is no matching, no balancing of proportion, no trying to get yourself to wear something other than the jeans you’ve been wearing all week. Ultimately, there is, “No thinking!” according to Yana. “Just pull one out of the closet and go.”

Sarah notes that dresses have also simplified packing for vacations. “Since a dress is a complete outfit, it takes up less room in a suitcase. As long as I’m traveling to warm places, which I always try to do, I can take dresses almost exclusively.”

Sarah, not worrying on vacation.

Could you do the same? Here is some wisdom that will set you on the right track.

Start with the right set of dresses

“I’m curvy and lots of things look pretty terrible on me, but I’ve worn dresses long enough now that I can recognize a silhouette or brand that will generally work for me,” Yana says. “Wrap dresses are a good bet. As is anything that ties in the middle. Or has an A-line, loose hanging cut. I’m also a sucker for bright patterns.”

How could you not be a sucker for this pattern?

Sarah says, “I am all about comfort…. I like thin straps in the summer and I can throw a cardigan over some of these for school. Most of my dresses are knee-length.”

Both women advocate a closet of abundance, “I wear dresses every day,” Yana says, “so it helps to have a lot of them.”

Below are a few styles that flatter most body types. These are worth a try.

Fit and flair, wrap, sheath, swing; looking good.

Accessories?

Styling dresses can be as easy or complicated as you want it to be, according to my friends.

Sarah says, “I can accessorize if I want to dress it up, jewelry or a scarf or nicer shoes, wild leggings, a sweater. Or I can go very simple: Just a dress and sandals.”

“I like a good pair of high heeled boots with my dresses,” Yana says, “brown goes with everything, but I also have a black pair. I also own a wide variety of comfy flats.”

Altering the accessories to face the weather is pretty straightforward. “I can throw on leggings if it is cold,” Sarah says, “Birkenstocks in the spring and summer, or boots in the fall.”

Sarah, on a simple style day.

Shopping secrets of the masters

The common theme of shopping between these two? The internet. Both women shop online, and Zulily is a favorite site. Apparently the site has interesting dresses and amazing sales.

Yana simply bypasses the annoyance of returning dresses that don’t work for her. “Because I can’t try them on beforehand, I limit myself to spending $35, often much less. Zulily, Modcloth, Nordstrom Rack all frequently have excellent sales. 4 out of 5 things I buy look good on me, the fifth I pass on to a friend. Everyone wins.”

Friends, did you hear that? This is an excellent plan.

According to Sarah “Since the dresses are not form fitting, online shopping works. I am also a sale shopper. I buy on discount sites like Hautelook, Zulily, two of my faves.”

Sarah, with her equally stylish family.

But all these sharp deals are fleshed out with an intermittent investment for Yana. “I will occasionally splurge and go to a local dressmakers in Silver Lake, called Matroshka. They make dresses custom fitted that are super adorable. But that’s a rare treat.”

That’s a new life goal. Thanks Yana!

It’s more than just a dress

As I am constantly uncovering on this blogging journey, clothing is never as simple as covering our bodies in a creative manner.

Sarah’s dresses have become legend among the girls at the high school where we teach. I’ve heard heated debates about favorite dresses, and philosophical speculation about just how many dresses Sarah owns. Given that Sarah’s job is to push kids past their comfortable limits in writing, she has to be down with being the hardline teacher most of the time. The dresses show a whimsical, relatable side of Sarah beyond deadlines and draft revisions.

A rare glimpse into the fabled closet of Ms. Prater.

Yana’s love of dresses, too, is about more than simplicity and flattery. “My mother never wore pants a day in her life. She grew up in a cosmopolitan Russian city and she always found pants on women kind of provincial. I think I saw her in a jumpsuit once. She wore it with high-heeled sneakers. She passed away when I was in my early twenties, and I think wearing dresses has made me feel connected to her, in some small, deeply comforting way.”

So for ease and comfort and human connection, I am challenging myself, and my readers, to a week of dresses. No need to buy anything new, (unless you find a sweet deal on Zulily…) just pull out the dresses you own, boots or sandals depending on the weather and give it a try. I’m not saying it’s gonna be easy. Yana and Sarah have had years to perfect this. You and I are gonna have to give up pants for seven days, cold turkey. But I suspect this will be fun. Next week I’ll post about my journey, and look forward to hearing about yours.

Can I do this for a full week?

* Meanwhile, those women are gazing back at me, envying my ability to earn a steady income, vote, enjoy central heating and access to quality dental care.

** Spellbound is one of my all time favorite films. It’s a documentary about kids in the national spelling bee competition, and it is riveting. It also won nearly every award known to humans, and was nominated for the rest.