self esteem

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

Dressember Reflection


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.

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Donate to my Dressember Campaign here. 

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

body image

body image

I've been really down on my appearance recently. I've had a few extra pimples here and there and I've gained 3-4 pounds (my weight fluctuates up and down in a 5 pound range, so it's hard to track what I've actually gained), and I've been angrily obsessing over it.

In moments of extreme self consciousness, I always recall a terrible night in high school spent crying on the floor of my parents' room about my horrible skin. That was my lowest moment.

As a perfectionist, I'm always buying and returning products, second guessing myself, putting myself down and trying to pick myself back up again. I also tend to be hardest on myself when I'm dealing with stressful situations that are largely outside of my control. And this year has been stressful! Mattress warranty issues, car maintenance bills, unexpected tax payments, loose tooth fillings, doctors' appointments. It's all piling up and when it does I turn to the easiest person to take it out on: myself.

I hate my hair, my teeth, my skin, my body. And I know that I'm being unreasonable and that very little has changed with my appearance in the past few months. I know it's caused by more than just a real dislike of my physical traits. But it's still hard. It leaves me feeling restless for change, for progress, for perfection. I keep asking myself what I can do to improve. Eat better, change skincare regimens, dye my hair. But I'm torn because part of my perfectionism insists that I perfect my character, and arrive at a place of total contentment with who I am sans all the cosmetic bells and whistles.

So I'm stuck. And I'm sure I'll find a way out soon. But I'd like to stop second guessing myself. I'd like to face the fact that life, appearance-wise, is all downhill from here anyway. It's ok.