Skip to Content

Dressember Update: But, Like, What Is My Personal Style?

The Dressember Challenge has been illuminating from a style perspective. When you’re forced to wear a dress every day in colder and colder weather, you either have to think long and hard about how to make the outfit work or just throw up your hands and layer up. I’ve looked like a kindergartner dressed up for recess with my sneakers, jeans, mismatched socks, and dress more often than I’d like to admit. It has not done wonders for my self esteem. (Don’t let the above photos fool you. Those were my good days.)

It’s really gotten me thinking about what I’m actually drawn to right now, because it’s forced me to pine away for certain items that just don’t work with dresses. 

I miss my boyfriend jeans, my Everlane u-necks, and all of my delightful sweaters (I looove sweaters). I miss the un-busyness of my normal clothing routine. I like special details, but I don’t need tons of crazy prints. I prefer to add unusual accessories and play with proportion rather than rely on a print to make things interesting.

This has not always been the case. I was obsessed with vintage printed skirts for a few years, for instance, but even then, I kept layering to a minimum. When I have to wear a dress in below freezing temperatures, I have to sort out where it will go in the layering lineup. I don’t find it fun.

Plus, I’ve been wanting to do more of an Annie Hall thing for awhile and I feel like my hair right now completes the look, so I’m bitter that I’m sitting here in a dress I’ve worn several times instead of my calm, collected, and casual look.

Another lesson that’s been reiterated for me during this challenge is that capsules wardrobes and I don’t get along. 

If you think about it, Dressember is a capsule wardrobe project because it prioritizes some items over others and limits the ways you can wear the rest of your closet. As a result, predictably, I find myself wanting to shop incessantly for all sorts of things just to mix things up when, in reality, I already have way more than I need.

I am lousy at persisting in things I find silly, or things that lower my self esteem. Dressing in a way that feels representative of who I am and who I want to be is important to me, and having to forego that has made me increasingly depressed.

I suppose this is a lesson that keeps in line with the anti-trafficking mission of the challenge. I’m sitting here annoyed and slightly sad that I have to wear dresses for a few more days while millions of people are forced to do all sorts of things they don’t want to do because they’re literally enslaved.

I’m temporarily “enslaved” to this dumb thing I thought would be super fun. That means nothing in comparison to actual suffering. Shame on me.

But also, maybe I’ve learned that I can raise awareness and donate to causes I believe in without wearing a dress every day. After all, I don’t like asking people for money. I’d rather share the message, raise money on my own, and encourage personal and sustained buy-in from the people I come into contact with. That’s the message I’ve been sharing with my coworkers and friends this Dressember.

Still, there are 14 days to go, and I’m trying my best to stick it out. I’m raising my hot toddy to everyone else participating this year. We can do this.


Donate to my Dressember Campaign here. 

(I’ll write you a haiku if you donate $10 or more!)

This site uses Akismet to reduce spam. Learn how your comment data is processed.

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: