Does This Outfit Make Me Look Insecure?

Liz and I were walking down the main drag in Westport the other day when we passed a group of high schoolers. We overheard:

“I have my first day outfit figured out, but I still need to buy my second and third day clothes.”

I remember being a version of that high schooler (albeit, one who only planned the first day). Specifically, I remember preparing for ninth grade and my first day of high school with particular care. My mom took me down to Jacobson’s, the Detroit-area department store, to shop, and I put together the best outfit: light blue jeans with more-than-average flare (we were en route to the ‘extra wide leg’ era of the late-90’s), a yellow fitted sweater, and, the best part, a silver necklace with block letter beads spelling M-E-R-E-D-I-T-H.

If only deciding what to wear on the first day could be driven by algorithms, instead of driven by our insecurities.

[For a shout-out to nineties fashion, the stress of outfit matching, and the iconic movie Clueless, click here.]

On that first day of high school, I wanted to be perceived as stylish, grown-up, and desirable to be around. My first day of school fashion efforts faltered quickly. I didn’t have the second and third day outfits planned, nor did I find any joy in doing so. After all, I didn’t value fashion; I only valued the approval it might give me if I crafted my image appropriately. And yet, through my first day outfit — and every comment, action, and homework assignment to follow — I sought the approval of every student, teacher, and administrator in that building.

To my surprise, when I started my new job in April, I was no different from that ninth-grader in the wide pants. I bought a new dress and blazer that struck the right balance of casual and professional. I got a reasonable haircut and even spent a minute considering whether I should wear make-up. While I’m more comfortable with myself in important ways, I could see the instinct of approval-seeking nonetheless playing out.

Opening a new school year and starting a new job are both entryways into new group formation. Our approval-seeking tendencies, which may be more or less activated in the day-to-day, are piqued by this newness. Uncertain about our status and situation, we bring reawakened questions of identity, inclusion, and approval. If I show them who I really am, will I be included? Will the real me be a fit for this role? And, more broadly, who do I have to be for you to approve of me?

When is the last time you picked out your “first day” outfit, designed your Burning Man costume, or dressed to make a particular impression? And what can those choices tell you about how you want others to perceive you? Byron Katie, in her work on thoughts and approval, suggests considering each item you pick out and articulating:

“With this <item of clothing>, I want you to think that <perception of you>.”

Or, alternatively,

“I am hiding this <part of self>, so you won’t think that <perception of you>.”

[From Byron Katie’s I Need Your Love — Is that True?]

What do these seemingly mundane choices about shoes and shirts tell you about yourself? How do you use clothes to manage your desired image? And what if you gave this up and dressed as your authentic self? I’m not suggesting there’s a right answer here, but instead an opportunity to look at something as tangible and seemingly inconsequential as your ‘first day clothes’ and get curious about what you can learn from it.

Meredith


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