Dressing on the Side: Creativity Loves Constraint

Rethinking the factors that help us get dressed every morning

In college, I took a class called History of Creativity. I wouldn’t have even known it existed as it was technically an engineering class and heavens knows I wasn’t browsing those course guides. Want your airplane to fall out of the sky? I’m your girl! But my dad was the professor’s TA 30 years ago and convinced me to sign up with promises of the humanities and having to go to the testosterone-filled engineering building twice a week—a building I quickly learned contained ½ of all married men on campus (the other half were in the business building).

Anyway, the class was fine. But to this day I still remember one phrase often shared by Google executive Marissa Mayer:

Creativity loves constraint.

When we think of creative people, we often think of people not bound by social norms or rule breakers. But that’s not all creativity is. The vast amount of creativity is taking a set of unique problems and coming up with a solution. Ancient people needed a way to get water from point A to point B. They had a certain type of material available to them to build with. It also needed to look nice. Enter aqueducts. 

And while it seems like having access to Martha Stewart’s pantry would yield a creative feast, the true test of creativity is putting something together from the one vegetable, three condiments, and leftover rice you have in your fridge. Or you take away all constraints (and taste and propriety) and you end up with Just In Case Cookies.

Give me some paints and paper and tell me to paint something and I’ll have a panic attack. Give me a picture to recreate and I can do it, making tweaks and changes along the way to make it even more beautiful.

So what does this have to do with this fashion column and when are you going to tell us who won the West of Breakfast pajamas, dangit?!

  1. Sometimes getting dressed this past year was hard because we had too few constraints

  2. We don’t value the constraints we do have as something that flexes our creativity

  3. Hold on!

Like I said in my last column, I leaned heavily into the no constraints dressing at the beginning of the pandemic. I didn’t worry about the weather, or being “professional” when I got dressed. But that did get old pretty quickly and I ended up relying on shopping to be my new “constraint.” I had to figure out how to incorporate this new garment into my wardrobe and once I did it, time for a new one! Our challenge got the juices flowing again and gave my creativity energy some direction. 

Something old, loungewear but make it fancy, something I want to come back

I also started to appreciate the constraints that I found boring. The weather, what I will be doing during the day, my desire to be comfortable. We often talk about those things as something that limits what we wear instead of figuring out creative ways around them. The team behind the brand Sonnet James, for example, used their desire to wear dresses while also being able to play with their kids at the park to launch a line of comfy and cute dresses. 

How can you start rethinking things that you believe keep you from dressing the way you want?

Something my mom wore in her 20s, Inspired by an album, My “cartoon character uniform”

And full disclosure. I didn’t make it the whole month without shopping. It just didn’t happen. But in the spirit of rethinking, I’m going to be ok with that. I think we often view fashion and clothes as something unimportant and frivolous, a hobby or pastime that is not worthy of time and money. And this sentiment often comes back to the fact that women find it important and fun. We are so quick to put down traditionally feminine hobbies and joys, thinking them less important than masculine hobbies. Heck, just go read some Cathy comics from the 90s. But I just learned how much some of my friends spend a month on a gym membership and that is socially acceptable. And while I do need to incorporate more ways to be ethical and purposeful in my consumption, I’m not going to feel bad about running my hands across the cashmere sweaters at J. Crew and thrifting a blouse every couple weeks. 

So if you didn’t follow along this month but need some constraints to get the juices flowing, pick a few from our challenge.

And finally, our randomly selected winner of the West of Breakfast pajamas is…@rebeccaluweka. She participated in EVERY SINGLE DAY! I didn’t even do that. And she didn’t just participate, she had a full blown photoshoot, complete with a location and props every day. As the Twitter youths say, she understood the assignment.

I think you all deserve pajamas.

Got a style question? I’m a Leo Sun, Pisces Moon, Virgo Rising, INTJ, Enneagram 6, and while I don’t know what any of that means, I think it means I really like giving advice. So at some point along the way here, I’d like to be the “Prudence” to your “Stuck in a Rut.” Want to know, “AITA (Am I The Adult Trying To Wear Juicy Sweats Again?).” Send your style, shopping, fashion, accessible fashion questions to . Or I’ll just make some up. That’s what everyone is doing on Reddit anyway.