The Only Question to Ask Yourself When Deciding What to Wear Every Day

Condition your brain for self expression

the one question to ask yourself when picking out what to wear

I’m pretty sure at this point in my style evolution I’ve succeeded in brainwashing myself. And Lord, am I thankful.

Years ago, I never would have felt comfortable wearing whatever I wanted, going to dinner with friends, to class, or a meeting in the exact outfit that felt right. Not “right” by social norms. which in the East Bay would be jeans and a Patagonia jacket (no shade there – if that feels right to you, that’s the whole point of this blog).

“Right” in the sense that the clothes you wear fit like puzzle pieces around yourself. Something just works.

The one question to ask yourself when deciding what to wear every day
From the Family Blowout in Brazil post

That Je Ne Sai Quoi

And I’m pretty sure that that “something” is as simple and as complicated as whatever it is that binds our inner identity to our environment. Both of which are almost always in a constant state of flux and influenced by innumerable factors. I’m not just talking about mood and weather, although those, too, play a role.

Your sense of style is political and psychological, has environmental and economic repercussions, and is a message to yourself and others about who you think you are.

One cursory Google search of “politics of pockets” leads to this 2016 Vox article, this 2014 Atlantic article, this 2019 Globe and Mail article, and this 2018 Guardian article, in that order. And that’s just pockets.

So, yeah. It’s complicated. Cue Miranda Priestly’s “cerulean” monologue from The Devil Wears Prada.

That being said, we live in a part of the world where we have agency over what we wear and how we express ourselves through our clothes. It’s huge gift, albeit I admit that it has different value to different people.

For me, the decision of what to wear always held value. My energy simply flows in that direction, and has since I was a kid. The exercise of either restraint or exuberance was always a calculated one. Most of the time, I just didn’t want to stand out. There was a pervasive shyness, a feeling of needing permission to express myself.

The one question to ask yourself when deciding what to wear every day
From the Burgundy Transition post

Learning the Obvious

And then life roughed me up a bit. Then it roughed me up some more. And then, still more – one challenge after another. Each round of, shall we say, “character building,” strengthened on the lessons learned from the one before it. With time, I came to understand that I’m my own person, the opinions of others weighing less and less on my decisions. I’m my own person.

Ta-da!

Who would’ve thought?

The one question to ask yourself when deciding what to wear every day
From The Holiday Guide post

Hey Malibu!

A turning point came after the accident (read more about that here). I had lost so much of my identity to a head injury, entered into a space of chronic pain, and had lawyers scrutinizing every action and decision I made in the ensuing legal case.

There were stretches of months where I would leave the house wearing sweatpants and no bra, something I would have never done before the accident. I just stopped caring – if people thought I was sloppy, that was fine. I had so many more fundamental issues to deal with than someone’s opinion on my sweatpants.

There were days when the only way I could distract myself from the chronic pain was by dressing up. So I’d go to Trader Joes in full makeup and stilettos. If people thought I was a wannabe Malibu Barbie, that was fine, too. I actually had someone yell out of their convertible, “Hey Malibu!” So what if they think I look like a ditz? They. Don’t. Know. Me.

The one question to ask yourself when deciding what to wear every day
From Outfit Formula post

And the people that do know me know that, in fact, I am a ditz, among other things. So there.

The “not caring” about other people’s reactions to what I wore became a habit. It started as an instinctual reaction to my life situation, but I also became more intentional about honoring it.

The Fundamental Question: What to Wear

I began to catch myself in the act of self-censorship. I would think, I should wear heels today. Graciously, the word should became a red flag. Did I really want to wear heels today? Sometimes the answer was “hell YES, gimme those stilettos!” and other times it was, “ugh, no.”

The fundamental question I started to ask myself was: “Is what I’m wearing today honoring what my day is about?”

Another way to phrase that is, “Is what I’m wearing going to help me feel more present in my life today?”

The beauty of the human mind is that it is built for habit. And while, for me, creating new habits is a s t r u g g l e, this is one that had legs. I now ask myself that question, in one way or another, every damn day.

The liberation is immeasurable.

From the Oversized Sweater post

Condition Thyself

And so, that’s why I say that I brainwashed myself. Over time, I’ve rewired my brain to be more open to self expression through fashion. I’ve remade the rules for myself, basing my choices more on respect for my reality (both internal and external realities) than on other people’s opinions. It’s a muscle to be flexed, that becomes bigger and more efficient with use.

So now, I see myself going out to dinner with friends wearing a “glorified bathrobe,” underpants, and stiletto slides. Or making a Target run in ripped sweatpants with epoxy stains on them because they’re hand-me-downs from Papa Mendes. Because the decision on what you put on your body, while more complex than we could have ever imagined, is also insanely simple: you do you.

So much love,

Stig.