To buy clothes or not to buy clothes? No. 28 on the list of things I waste time worrying about.

When I was younger, there was no question: I desperately wanted trendy new clothes, which led to constant battles with my thrifty mother.

My mom stayed home and my father was in the Navy. Although we didn’t want for anything, we couldn’t have had a lot of spare cash with three kids in the family.

Even aside from that fact, my mother wasn’t the type to spend a lot of money on new clothes, whether for herself or for me and my sisters. She was raised by my grandmother, who grew up in a village in what is now the Czech Republic, lived through both World Wars, immigrated to Vermont in 1949 with nothing, and made all of her daughters’ clothes by hand, including their wedding dresses.

Thus, my mother scoffed at brand names, and our yearly back-to-school shopping trip was fraught. (Mom, if you are reading this, I’m nothing but grateful now for the thriftiness you instilled in me.)

I’m aware that this isn’t a story of hardship. But I was insecure for a long time, like most kids—especially girls—are. If I had been different, had known better, been more self-possessed, I could have avoided a lot of angst, but instead I desperately wanted whatever the new fashions were at the Limited and Express every year. (In retrospect, my sights were set low, but I spent my high school years in Virginia Beach, not exactly a fashion capital).

Things didn’t change too much in college. I got some spending money from my parents, and worked over the summers. I think I pretty much looked like everyone else, but I was still envious of the content of other girls’ closets, and my clothes still felt closely tied-in with my sense of self-worth.

After college I found myself in Washington, D.C. with a decent paycheck. For the first time in my life, I started to spend money more freely on clothes and it felt great. I remember catching a glimpse of myself once in my apartment hallway mirror in Nine West boots, a Banana Republic dress, and a Benetton coat, and feeling like my brand-name garb was armor against the world. It made me feel secure and protected, and I liked it. A lot.

Then I moved to a camp in Alaska for a summer, where I was the only girl who wore lipstick (really tinted lip-gloss) and showered every day.

After Alaska, I moved to Austin. Austin’s a casual town, and it’s always 90 degrees, so a lot of my nice clothes continued to languish in the closet. I never made much money, so I just got out of the habit of buying “expensive” new clothes. I wore tank-tops and flip-flops most of the time, and I found lots of cute stuff at thrift stores. Finding designer or brand-name clothing at thrift stores was deeply satisfying to my thrifty soul.

Plus, I was in a serious relationship, and my boyfriend really didn’t seem to care what I wore. It started to seem like vanity—in addition to a waste of money—to try to wear nice clothes or look hot. Who was I trying to impress? I should want people to like me for me, not to be impressed by my clothes or looks.

And then I became a lawyer, moved to Seattle, and started making more money. At first, I still had the same attitude. I didn’t have time for thrift store shopping anymore, so I bought new clothes for work occasionally because it made my life easier and I could afford it. But the “work me” didn’t feel like the real me, so I didn’t much care how the “work me” was dressed. Even though I was single again, I still felt like it wasn’t quite right to care too much about how I looked.

Over the last few years, though, my habits have been changing. I’ve started shopping and buying new clothes more, and spending more time trying to look nice. I wear makeup more often, and I’ve figured out a work style that works for me—no more black pants, button-down shirts, or pumps. Luckily, I live in Seattle, where it’s easy to get away with being casual. I’ve been really enjoying feeling like I look cute and stylish, even if it’s only in my head. I can’t deny it: I love having things in my closet that make me feel comfortable, pretty, and stylish, and I love buying new clothes. It’s delightful.

But I’m torn. Money-wise, it feels like a bit of waste. Shouldn’t I be using that money for other things, like travel or classes, or saving it so I can work less in the future? Or giving more to charity?

I’m also uncomfortable with my motivation. I’m not sure why looking nice matters.

On one hand, I think it does matter to my husband. He likes it when I’m dressed well. He’s not a fan of some of my more Bohemian choices, but he generally likes my style. Making him happy seems like a good reason to try to look nice, but I wonder whether I’m just using him as a convenient justification.

This may be the root of my discomfort: if I’m honest about it, the pleasure I get from feeling like I look nice isn’t just a matter of aesthetics. There is a competitive, or at least comparative, aspect to it. I enjoy it at least in part because I feel more attractive and more stylish than other people. And that doesn’t seem like a good source of happiness. I can easily forgive my younger self for needing that kind of validation, but at this point in my life, I don’t know. Do I take any pleasure in wearing nice clothes that doesn’t have that comparative aspect?

I don’t know what the answer is, and I know there are much bigger things to worry about—both in my life and in the lives of others. But feeling guilty whenever I buy new clothes and spending as much time justifying it to myself as I do seems awfully inefficient, and yet I don’t want to give it up because it’s too fun. I’m seriously curious about whether or how other people feel about these things.

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