Close Encounters of the Whimsical Kind

Consider this your permission slip to express yourself

When it comes to clothes, I’ve always been drawn to the whimsical. A rainbow-striped hem line, a cheeky saying on a t-shirt, an unexpected pattern, a pop of color.

I remember when I was a young teenager, I so badly wanted my mom to buy me a particular graphic tee at Hollister. This shirt had a donkey on the center of its chest, with the word “Jack” printed above it.

…Cute, right? *rolls eyes*

At the time, I thought this was so funny and as a bit of a goody-two-shoes, wanted to express myself in a way that claimed otherwise. That told my middle school peers, I have many sides to my personality!

In retrospect, I’m glad my mom refused me on that one. As a consolation prize, I ended up with a pale pink shirt with a single word repeated three times: “blah, blah, blah.”

It seems I’ve held on to that love for sassy sayings from my youth. As I write this, I’m coincidentally wearing a cozy mauve sweatshirt adorned with the words “per my last email,” a nod to the email lingo that permeates corporate culture.

My love for fun, witty fashion can be attributed largely to Kate Spade, the epitome of whimsical design.

I remember the joy that came from perusing the Kate Spade store with my mom growing up, or with my friend Julie in college. You didn’t even have to buy anything because simply scouring the store delivered an instant dose of inspiration.

I remember the lollipop-striped swing dress my mom splurged on to wear to my college graduation. Me, alongside her in the photos wearing a bright coral shift dress with a scalloped hem.

I remember the red cheetah-print Current/Elliott jeans I’d wear in college, standing out from my peers in their regular jeans and sweats.

I remember the breezy sleeveless blouse I got at Anthropologie, decorated with tiny pastel-colored mopeds.

I remember the J. Crew jeans that were a sea of garden flowers, set against a backdrop of cream denim fabric.

I remember laying eyes on a beautiful pair of sandals with a heel reminiscent of cork and straps with multi-colored stripes wrapping around the ankle and the toes. I knew I had to have them, for they were the perfect color neutral.¹

As I’ve gotten older and my tastes have evolved alongside today’s trends and what I value in my wardrobe, there’s been a bit of filtering out. My jewelry box is no longer filled with dozens of chunky necklaces and baubles, and is instead occupied by simpler, smaller jewelry. I still covet the occasional statement earring though, as evidenced by my champagne bottle earrings I save for special occasions.

I have “upgraded” my closet as well, filling it with classic, timeless items like solid-colored cashmere sweaters and good-fitting pairs of denim (blue, not cheetah print and floral).

Like my jewelry though, I still opt for the occasional whimsy—my white cotton blouse with tiny Eiffel towers, bicycles, and hearts printed all over it comes to mind.² Or the pair of bright, fire-engine red Nike sneakers made in collaboration with French designer Jacquemus.³

Given my love for the whimsical, you can imagine my excitement when I recently spotted this bow-tie pasta patterned jacket while browsing for my latest Nuuly box.

Pasta printed on a black puffy coat? How totally out of place in the BEST way possible. I immediately hit “add to Nuuly.”

When the box arrived on my doorstep Thursday and I tried this jacket on, it was instant amóre.

The following evening, while figuring out what to wear to a book talk at a cookbook store, I knew I had to wear this. It couldn’t have been a more apt occasion.

Little did I know just how happy I'd be to have worn that coat.

I headed out the door on Friday night to attend the book talk solo. I don’t often attend events by myself, so this was a bit out of my comfort zone. But I figured it’d be no big deal since any book talk I’ve attended in the past has been mostly a sit-and-listen kind of affair with little socializing expected amongst the audience members.

However, immediately upon walking into the shop that night, I realized this was a different situation. Attendees crowded the shop, all animatedly chatting with one another in groups of twos, threes, fours, likely the people they came there with. Due to the nature of the store’s layout, there were very few seats and it was clear the interview part of the evening would not be starting right at 6 as I had assumed.

With no seat to claim or obvious “welcome” to this event, I felt all too aware of my aloneness. Fortunately there were dozens and dozens of cookbooks to peruse as a distraction. I kept reminding myself that no one there would care that I came alone, let alone notice.

Then came the first voice behind me, from a gray-haired woman who appeared to be there with her husband. “I love your jacket, where did you get it?” Relief washed over me as this stranger acknowledged my presence. “I'm actually renting it from a company called Nuuly!”

It was probably no more than five minutes later when the shop’s owner announced the book discussion would start in 20 minutes and to please help yourself to some of the food and drink they had available.

Twenty minutes!? I thought to myself. How am I going to last that long with no one to talk to?

This time food was the distraction as I made my way towards the counter in the back to grab a non-alcoholic aperitif.

Another woman’s voice filled my ear - “oh my gosh, that jacket is wonderful!” “Thanks," I smiled as I dished up some noodles.

“That jacket is so cool!” came the greeting from another woman, her face a warm, welcoming grin. I chatted with her for a moment as I topped my plate with some crudités and spicy cilantro sauce.

Meandering my way back into the middle of the store where I could safely claim the cookbooks as my companions again, a middle-aged woman in a blue striped beanie exclaimed, “I love your jacket!”

Unlike the other folks, she didn’t stop at the compliment, instead taking her interaction a step further. “What brought you here tonight?”

Whether it was her earnest expression or my inner confidence building after several compliments on my outerwear, I’m not sure, but I found myself replying with utter honesty. “Have you by chance heard of The Artist’s Way? This is my first artist’s date!”

She had, applauding me for my date of choice and then proceeded to share with me that she was friends with the author’s cousin and what great people they both were.

Our conversation flowed easily from there, lasting long enough for her to ask me my name and tell me hers (Leanne) before she migrated back to her partner's side.

The book discussion happened shortly thereafter, enthralling me as I finished sipping my beverage. I would've preferred it go on for the rest of the evening, my mental talk-to-a-stranger box checked, but the talk ended leaving close to an hour of time left.

I could’ve easily called it a successful evening and bailed at that point, but I was emboldened by the interaction I’d had with Leanne and felt compelled to stay. To eat some more of the tasty food and see what other conversations might occur.

A couple more comments on my pasta jacket came my way as I floated around the shop, feeling out whom I could talk to next. Upon purchasing the author’s book, the shop’s owner complimented my coat and said it'd be the perfect thing to wear to their pasta-making class.

When I saw Leanne pass by, I called out to tell her that I appreciated the question she had asked during the talk. We proceeded to have a wonderful conversation about aging, communal living, and intentional gathering for the next ten minutes or so, a connection that meant a lot to me.

Then I eagerly approached two women to tell them their book club sounded so fun, a tidbit I’d learned from their question to the author earlier.

They too noticed my coat and gave it praise. I intended to ask them how their book club started but was interrupted when a neighbor knocked something over between us.

The moment over, I started to shuffle toward the exit, my feet deciding to make one last stop before my brain knew what was happening. I stopped in front of the author, noticing she was free, to ask her more about something she’d shared.

We talked for a minute or so about the nature of the public school food system, me thanking her and finally calling it a night.

But not before she said, “that’s such a great jacket!”

Selfie prompted by my post-event high.

That pasta puffer proved to be so much more than a fun fashion statement—it was the conversation-starter I unknowingly needed to connect me with strangers.

The bow ties took the place of the words my mind couldn’t find, calling out to others, “Hi, I’d love to talk to you!”

I’ve always loved whimsical clothing for the way it allows me to express myself, but now I love it even more for its power to spark a connection. 🍝

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If you enjoyed this post, you might enjoy these musings on clothing:

An Outfit, or Shining Armor?

Is it just me, or is every millennial in a style slump?

1. I firmly believe you can wear pretty much anything with a multi-colored pair of shoes or clothing, thus making it a neutral in my book. You didn’t ask, but I also subscribe to the cheetah-is-a-neutral frame of thought.

2. What is it with American clothing brands’ obsession with a nod to the Latin European countries? I fall for it every time. But of course the women who live in these places don't wear such a thing. 🙃 That’d be like me, as a Portlander, wearing a t-shirt with bridges or the white stag sign printed all over it.

3. Fawning over the red ballet flats trend of this past fall, but conflicted over how much I’d wear such a thing, these sneakers were my own expression of this trend.