The Journey of a Thousand Dresses

It was a warm February day in Arizona when vintage super maven, Suzanne Carillo, and I got ready to go meet up with newfound blogger friends at a restaurant. She put on a dress, while I chose jeans and a forgettable top. In the last seconds before walking out the door, I mentioned how nice she looked.

“It’s one of my Karina dresses,” she said. “I don’t travel without them.”

Between the two of us, I suspected she was more comfortable. Her dress draped easily with stretch for movement. Plus, the heat gets to me now like it never used to and her dress just seemed like it would be cooler. She also looked more grown-up and more put-together than I felt in my denim uniform.

“I don’t wear dresses, much,” I said without thinking. “I just feel safer with something on my legs.”

From the look on Suzanne’s face, this choice of words struck her as odd. She was too nice to say anything then but looking back on the conversation, it struck me as odd, too. Had she asked me more, I wouldn’t have been able to explain it, but I’ve come to learn that “safer” was a good word to describe why I didn’t gravitate to dresses outside of special occasions*.

In my mind, I was:

  • Safer from the wind blowing up and exposing what was underneath.
  • Safer from the men I had always been warned about.
  • Safer from my own fear of showing my pearly white legs.
  • Safer from jabs of others making fun of my pearly white legs.

*Note: My brain worked around this issue for special occasions because I covered my legs with pantyhose. This took care of the pearly white issue and gave me a sense of security under my dress.

Suzanne’s ability to walk around the earth in a dress without all those fears coming true made me examine whether it was worthwhile to cling to my old notions about these things. Those ideas came from a time and a place I no longer lived. Maybe it was time to toss them into the same bin I’d tossed other outdated ideas.

From that point forward I started making a plan that would put those ideas to the test. From May 1st to May 31st, I wore a dress a day, even on rainy days and days I had no appointments to go to outside of my condo. The only exception was when I worked out.

The results of my experiment will be unveiled over the next several weeks in posts to come. I admit that it was more difficult than I expected. For starters, early May in Seattle is not often “bare legs” weather, so I made some exceptions about going sans tights during this time. Once I got into the groove—and as the weather warmed up—I started to learn quite a bit about myself, my old ideas, and whether those ideas still served me well.

A very good dress to start.

Let’s start with a dress that made the transition easier: a Steven Alan dress I bought with credit on It has the look of a shirt dress because it buttons down to the waist and has a fold-over collar. The black and gray gingham suits gray and rainy pre-summer days here in Seattle, as do the long sleeves that I roll up on warmer days.

black and gray gingham shirt dress from TheRealReal paired with blue ombre tights, an obi belt and loafers.

I like this dress because of the style, but also because I can layer it with tops underneath, as well as tights or even (gasp!) skinny jeans on cooler days.

Steve Alan dress with BZR ombre tights, Halogen loafers, and costume jewelry.

Speaking of tights–these locally made, super cool ombre tights by BZR make everything feel a little more dynamic. The black-to-gray version was featured in my speakeasy style post last week. The ones I wore with this dress are called “denim” because they go from denim blue to faint lilac.

Did you think I’d be able to give up my denim habit completely?

BZR ombre tights in denim with Halogen loafers from Nordstrom.

The loafers are Halogen brand in “Emily” style. I got them last fall during a sale at Nordstrom. They’re on clearance now and there is a perforated version that might be even better for summer. They’re on sale as well.

Steven Alan dress with an obi belt by Eileen Fisher and costume jewelry from Etsy.

The “denim colored” vintage beads are from VintageStarrBeads on Etsy. The store owner is a hoot to deal with. She also has a wide selection of vintage jewelry.

The obi belt is also somewhat vintage. I bought it new from Eileen Fisher a long, long time ago–too many years to remember. I like how it cinches this dress “just so” because, without it, the little pleats at the waist can make me feel self-conscious around the belly.

Put on your sunglasses. Things are about to get very bright.

And now, what you’ve all been waiting for, the dress worn on a warm, sunny day, without tights or undershirt. Pardon the wrinkles on the dress and my pearly white legs underneath it.

A little voice in my head is screaming, “ACK!”

Steven Alan black and gray gingham dress with Geox blue flats.

I even took off the obi belt because, when it’s hot outside the the last thing anyone needs is a leather casing about the waist.

Steven Alan black and gray gingham dress with blue Geox flats.

The flats are new loves from Geox. They are soft on the heel (no blisters) and they have support inside. They’re on sale at Nordstrom as well. I loved them so much I bought a second pair in black.

“Can’t Touch This”

Over the course of May the weather warmed up and I ventured out in this dress without tights or other layers. It wasn’t until then that I really understood the value of this style–the wind couldn’t touch it. Like most cities, Seattle can be super windy. The slightest breeze off the water can turn into a full-scale skirt-floofer by the time it reaches my neighborhood a few blocks up. I never had to worry about that with this dress and, as I discovered later on, that is something to be very thankful for.

The impact of this one small shift in my life has been surprising. It changed my perspective in ways I never would have imagined prior to starting out. I hope you’ll join me as I continue my quest with The Dress!

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  • This dress is super-cute on you. And now I get the whole dress-for-a-month project. What a great project to expand not only your closet but also your self-confidence by shedding all that thought-weight. Pale legs are in!, I hope because mine are as pearly as yours. It makes sense that this epiphany came about when you were with Suzanne. I look forward to your next posts.

    • If pearly legs aren’t in, maybe we can start a new trend together! It is sort of freeing, now that you mention it, to not worry so much about some of that stuff. Lots of shedding of those kinds of thoughts took place in May. I can’t wait to share more. And I’m contemplating videos too. 😀

      Yes–epiphanies and Suzanne go hand in hand. I wonder if she’s actually just some sort of angel sent here to kick our booties about living whole lives? 🙂


  • I think it is interesting the mental ruts we can sink into over our lifetime. We don’t even know they are there. Our internal dialogue controls everything from what we eat, who we hang out with and what we wear.

    I think it is a good sign when you are open enough to still want to try new things. It keeps you young and adventurous. Most people are happy and comfortable with the status quo.

    Your blog is internal journey for you in so many ways and is very interesting reading to understand how clothing changes your mindset. Not only will it change you, but it will change the way people respond to you.

    Great post Sherry!


    • It’s easier to challenge beliefs and expectations when surrounded by loving others who can reflect those beliefs and expectations back in a way that is gentle but catches you off guard and makes you think. You and Melanie and Sue, among others, do this for me all the time with your blogs and our conversations. I’m constantly considering what works and what doesn’t work. Yet another value to cultivating friendships outside one’s own small world. 🙂

      And I agree with you. My 94-year-old grandmother would agree with you. To be open to new experiences and try new things keeps you young and alive. My grandmother told me once that she could lay on the couch and just watch TV and die, or she could get off the couch and go do something new and live. And she did. Until she couldn’t drive herself anymore, she volunteered bi-weekly at a clothing room that served the underprivileged in her community. (In some ways, she was my first intro to thrift shopping! ha!) She set the best example for that idea in action.

      Thank you for your friendship and your reflection, Suzanne. I’m so blessed to have you in my life.


  • Your pearly whites are BEAUTIFUL!!. They are a “healthy” color! You are without marks of any kind!(how do you pull that off? )

    • Ha ha! Oh, Jude, you are too kind! If you saw my legs in person you may not think they are without marks and a healthy color.

      A friend once told me that our upbringing is like being pickled a certain way. It takes a lot of work to squeeze out all that brine and vinegar and, even then, a little bit of it will always remain. I like to think that if I take the time to sort through what I was pickled in I can come away freed from what doesn’t serve me well and stronger in the things that do help me live fuller and truer to my core being. Little by little I’m learning how to say “fark it” to those things that don’t work well anymore.


  • Dang !!! I wasn’t done!
    You look so cute in ALL of these styling variations Sherry!
    Why is it so terribly difficult to get over these socially imposed evil notions of what is acceptable! We must find out how Melanie overcomes these so artistically and just says, “fark it!!”

  • Wow, what an insightful post. We all carry limiting ideas in our heads and most were planted there during childhood by others. It’s incredibly valuable to examine these ideas now and decide, consciously, if we want to retain them or not. In most cases, we don’t because they hold us back from freedom and happiness. I look forward to your future examinations of the dress-experiment.

    • Thank you, Ally! As I said to Suzanne above, deciding what works and what doesn’t is easier with a support system such as what I’ve discovered through blogging. And I dare say you are a valuable part of that community. The insights and reflections I receive from you open my world more and more. And what a wonderful world it is to see those of you walking with me on this journey sparkling with your own personal lights. It is heartening and warming to look around and see you there and know I’m not alone in my journey.


    • Nancy, you are a marvel the dresses and skirts you wear. Because you always look so put-together and lovely in your outfits, you are among those who inspire me to keep trying new styles to find what works best.


  • No making fun of your legs because mine are even whiter!! I’ve been learning to embrace my whiteness, so it has gotten easier!!
    But you’re right about the wind factor….certain dresses are way better than others for that!
    In fact, that’s one of the reasons I like maxis!!
    You look fabulous Sherry!!

    • It’s all about embracing who we are, really, don’t ya think? Whether it’s about legs or eyebrows or how I look in this or that, learning what makes me feel good about myself is as important to this journey as being humble about areas where I lack beauty, skill, talent, etc.

      I didn’t explore maxis much in my experiment, to be honest. They were harder to find at the length and price point I needed, but they are on my list of things to try as soon as possible! I like the idea of not having to worry so much about wind.

      Thanks for stopping by, Jodie!!


  • Oooh…I love this concept of wearing dresses for a month.

    Now, where to begin?

    When I got back into sewing clothing, I realized I loved making dresses. And I loved wearing them….some of the time. My handmade wardrobe is crowded with fit and flare dresses, shifts, tee-dresses and, recently, shirt dresses! Yet….I still struggle with wearing them as frequently as I really want to.

    I have a mental list similar to yours. The paleness and shape of my legs is pretty much first. Nylons add colour and they also look slimming, but I often find the fit not quite right. And, of course, when it’s hot…I totally don’t want to wear them. That being said, I actually am wearing my dresses without hose or leggings in warm weather and not feeling completely self-conscious.

    Okay…this one is a funny one. When I wear a dress, I frequently smooth my backside, and not because I’m getting fresh with myself. I have a fear that my dress has ridden up or worse, gotten tucked into my drawers??!! Many years ago, a girl I worked with had a job interview in a grocery store. The offices were at the back of the store and when she left the interview and walked down the aisle towards the front exit, she got all kinds of looks. Yep…her skirt was totally tucked into her pantyhose.

    I also feel the need to move….and um…do the man spread. {NO NOT REALLY} And pants just feel easier…ie all my favourite authors are on the top shelf or the bottom shelves of the library. The squatting and the reaching…I don’t think twice if I’m wearing pants…but if I’m wearing one of my dresses, I find myself struggling sometimes….

    Okay…keep it coming. I need to read more about this. One things for certain, I won’t stop making dresses. And I want to wear them more often!

    • Sue, you seem to understand completely! I have long thought how smart other women look in their dresses and I even buy them, but they have hung in my closet until I find that perfect occasion to wear them or until I finally give up and send them to a new home.

      I think about the “pantyhose tuck” issue myself! Ha ha! I’m glad you brought that up! I suppose going without pantyhose makes it a little less of a concern, but then you have the issue of being exposed completely if the wind catches just right. I’m covering a little about that in the upcoming post about wrap dresses.

      And the climbing up onto step stools, the bending, the reaching, going up stairs that have openings so people underneath can see straight up — these are all issues I’m re-encountering with dresses. And yet…they look so good, they’re comfy, they’re easy to style. So, I think they are worth dealing with those other concerns from time to time. Especially if they make me feel good/confident otherwise.

      Thank you for your comments! It helps me shape the future posts and know I’m not completely alone in this. 🙂