How I Go About Picking An Outfit For Something Important

The chaotic process for wearing something meaningful.

Choosing an outfit for something important is not a simple task for me. It takes days of deciding every little detail. What color should I wear? Should it be a dress or pants? Will I be too cold? Too hot? What’s the vibe? Then after I find some options, I panic text all my friends, who probably don’t care all that much, but tolerate my annoying asks.

Reading this may make this process seem chaotic and miserable, but the reality is that it's actually fun for me. Using an outfit to send a very specific message is the reason why I love clothing so much, and picking said outfit is like my Olympics. There’s the preparation through the little decisions I mentioned above, the anticipation, and then of course the big reveal where you see if all the thought and effort you put into the look actually paid off.

I unironically had this Olympic moment a few weeks ago.

Since the pandemic, I haven’t had to think about outfits for big events or trips for work. I haven’t bought much clothing, aside from a few vintage swaps here and there, and mostly, my closet has been pretty static. I realized, though, that I may need some new photos of myself for professional things (like my book "Worn Out" that comes out in September!) so I coordinated a shoot with a wonderful photographer named Louisa Wells that we shot in Bushwick, Brooklyn.

Because it was a special moment, I allowed myself to buy one item for the photos. So I had to answer my questions.

What’s the vibe?

I absolutely hate getting my photo taken, so the only vibe I really wanted my outfit to read was professional but not uncomfortable. I knew that it would take a lot to get my body and face to relax, so the last thing I wanted was some awkwardness in the outfit.

What color should I wear?

After some careful consideration, I decided on blue. I wanted a lighter blue because I have blonde hair, and I think that complements it nicely. Also, blue can stand out, but it’s also serious. I wanted the tone of the photo to reflect the way I feel, friendly but also dedicated to my work.

Should it be a dress or pants?

I opted for a skirt and top. I actually don’t wear skirts or dresses all that often, but I thought a classic silhouette with a black skirt was the right mood for the photo.

Will I be too cold? Too hot?

This was interesting for me, because although it was going to be cold outside, I wanted to show off my scars. The biggest of which is on my right arm. So despite the fact that it was 20 degrees, sleeveless was the move.

Vintage or new?

Vintage. Almost always vintage.

In the end, I opted for a light blue sweater crop top from the 1999 vintage Chanel collection that, I found on TheRealReal. I felt it communicated my love for fashion in a way that only an outfit really can.

*This Stuff is a newsletter by me! fashion journalist, Alyssa Hardy. Three times a week, I unpack the ways our clothes impact the world through news, essays, interviews and more. Subscribe for free here and follow me on Instagram, Facebook and Twitter.*