The Year I Decided To Dress Like Myself

I am an unabashed New Year’s resolution lover. I understand all the arguments against them. They’re cheesy, people don’t stick to them, and you should just make changes on your own timeline — there’s nothing special about the new year.

I also disagree with all the arguments against them. First of all, making a change you want to make for even a few months is fantastic. It’s not a contract you signed to change for the whole year. And second, the people who hate New Year’s resolutions are ignoring one simple thing: You can pick something fun. You don’t have to make a resolution to eat healthier or run a half-marathon or clean out one room of the house every month. A friend introduced this concept to me years ago. (Hers for the year were to eat cake more often and to “try more butt stuff.”)

I love the idea of changing yourself for the new year. Of rebirth, or growth, or simply a reminder that we aren’t static and we don’t have to be. That there can be new practices in our lives that bring joy or, yes, if you must, lower LDL cholesterol levels. I like being reminded that who I am and what I do isn’t set in stone, isn’t locked in. It’s not just that I can create goals around unfun stuff like work. I can also create goals to have more fun. In 2018, my goals were to make homemade pasta once and to get into skin care, and I did both! I felt unduly accomplished!

In the spirit of this, last year I decided that I needed to dress better. Not nicer but more fun, more fashionable, more me outfits. I have what is medically known as Too Many Clothes. I come by this somewhat honestly. My mom and dad both have more clothes than a person could wear in four lifetimes. My father, who grew up very poor and overweight, has a particularly obsessive relationship with clothing. He has kept many of the few shirts he owned as a child, and can still describe how purchasing each one made him feel; as an overweight kid with very few options, certain clothing items felt magical to him. They were a source of self-esteem. Once he lost weight and got a job — at a department store, selling clothes — his love affair really took off. When my parents eloped to Italy, where his father was born, he spent at least half of their honeymoon shopping. He used to pick out outfits for my mother. He subscribes to women’s magazines to this day just for the sake of seeing nice clothing. He has clothes that no longer fit or that he will no longer wear that he cannot bear to part with for sentimental reasons. Growing up, he had closets in three different bedrooms in the house and dressers in even more. His clothes are everywhere, spilling over chairs, lovingly wrapped in the dry cleaners plastic they came home in 20 years ago, laying flat to dry.

He passed the disease along to me. Clothing is my hobby. It matters to me in a way that might make you laugh if you saw me running to CVS ever. This presents a problem for a couple of reasons: one, it’s expensive to buy new clothes, and two, it’s very bad for the world. Both of these things make me feel guilty often. I don’t spend much on any item of clothing — the most expensive thing I own by far is a $150 winter coat — but I used to buy often. Any extra money I had went to clothing. The problem is when you love and covet new clothing but you don’t have lots of money, you end up buying fast fashion, which is destroying our planet.

I realized for years that I needed to stop. I would quit buying clothes for a few months only to relapse in a fit of post-10 p.m. boredom. Finding clothes that made me feel good about myself just felt so wondrous, so miraculous. So worth my money. (It’s very funny to look back at photos and realize that an outfit didn’t look as good as I thought.) Finally, I accepted that clothing was something I loved, something I cared about and that it was unlikely that I would stop buying new things outright. So I made a deal with myself that I could buy all the secondhand clothing that I wanted, and I could buy new things for special occasions. I supplement this with a clothing rental subscription to give me the “fun” of new clothes without as much new production and consumption.

The plan isn’t perfect, but it has mostly worked. Except it has not cut down on the amount of clothing I have. Clothing I wear to… nowhere. I work from home for the most part, my big outing of the day being a walk to a coffee shop and the walk back. The pandemic only made it more clear how little wear I was getting out of the things I’d spent so much time and money shopping for, organizing, and laundering. And from this frustration with myself came last year’s resolution: wear a fun, fashionable outfit every single day.

There’s no reason you can’t dress up to go to the coffee shop or the grocery store or your living room. No one is going to stop you and make you answer for your outfit. Looking foolish is absolutely fine! In fact, I encourage it!

So I began to dress up. Often, I picked out a piece of clothing that I hadn’t worn in a while (or ever) that I wanted to keep but that I wasn’t wearing, and then I challenged myself to make an outfit with it. If I couldn’t, it was a pretty good sign I needed to donate it. It took me longer to get ready, but I also was actually enjoying myself. And I was enjoying my clothes. Occasionally, I made stupid missteps like walking a mile with previously unworn patent leather oxfords, which gave me terrible blisters. Sometimes, I discovered (or rediscovered) the hard way that a sweater was itchy or that a pair of pants was too tight in the waist to be comfortable. Sometimes I ended up hating the whole of my outfit, even though I loved the parts. But for the most part, it was an exercise in being bolder, in not being worried about whether anyone else but me liked it.

It all paid off when after a few weeks, the barista at my coffee shop — a very stylish man himself— asked if I worked in fashion. I rode that high for weeks. I mean! What a payoff. A little while later, I got an in-person job with very well-dressed co-workers and customers, and the whole project fell apart. I tried to dress well for work, but I always felt like I was dressing for people, and the job involved being on my feet a lot and carrying things and bending over and cleaning up messes; the requirements for work outfits exhausted me. I stopped having fun with clothes.

Recently, I left that job and started working from home again. And I’m back. I’m trying new clothes and looks. I just got into baseball caps after years of longing to pull off a look I saw a beautiful woman wear on the streets of New York. I’ve relaxed my resolution a bit — I’m not going to lie, wearing An Outfit every day is a bit much — but I also came back to it. Because it’s fun! Because you get to have fun with personal changes. You don’t have to make your body or your mind go through hell or work harder. The challenge is to have more fun.