I Don’t Buy the Outfit — I Buy the Promise

Clothes are rarely what I want them to be, and it’s because I expect too much from them. I sometimes feel like I’ve been waiting my whole life to put on something that will unlock an aspirational version of myself who says the right things and knows which fork to use and never makes any mistakes, ever.

I know that this kind of transformation is not something any $20 shirt or $200 dress can do, but I keep treating my clothing purchases as promises. Most of the effort I put into my appearance is in the actual acquisition of my clothing, because I think if I can get it right at the store, everything will go well from there. The right dress will make a smooth first impression; the right shoes will land me the job.

I don’t buy clothes frequently enough to not assign a lot of meaning onto them. Shopping is a necessary chore that comes up every couple of months, not my preferred way to spend a weekend afternoon. I often leave stores empty-handed and frustrated with myself because I’m probably too picky. I dislike certain fabrics and cuts and I tend to stay away from anything that feels like a passing trend. I usually have specific things in mind when I go to the store, and often want an item that’s nearly identical to something I used to own, or currently own but is getting worn out or faded.

Maybe if I had an overflowing wardrobe, each individual piece wouldn’t have to carry as much weight. My clothes could just be clothes. But for now, here are some items I bought, the promise I thought they were selling me, and whether or not they lived up to it.

I bought a romper during my junior year of college. It was black with white hearts printed on it, and it laced up the sides. It was from H&M and cost something like $15. I thought I was being clever by getting “a whole outfit for that price!” I wore the romper to a few parties with tights underneath because it looked suspiciously like I was wearing a dress and I didn’t want anyone to think I would wear a dress that short.

When I bought the romper, I was actually buying the idea that I could be cute in the fun, trendy way everyone around me seemed to be. I’ve since become comfortable with the fact that I’m not. Also, I’m sorry but rompers are terrible. I once had to totally remove the entire thing in a tiny, dirty bathroom just to pee while at a college house party, and this is something I wouldn’t wish on anyone.

In 2014, when I was a grad student and freelance photographer, my then-significant other was a law student. That spring, I found myself in need of a gown to wear to the barrister’s ball, which is basically prom for law students.

I went to Lord & Taylor and found a Ralph Lauren gown with an illusion neckline decorated with understated black beads. It was a simple black dress, free of too many details like ruffles or lace. It was the nicest thing I’d ever worn in my life, and I knew I had to have it even though the $120 price tag (a significant markdown from the original price) made me feel guilty. I swallowed my feelings and paid for it using a $50 Visa gift card and $70 in cash that I’d cobbled together from recent photography jobs.

The dress promised that I’d be glamorous and attractive but still “taken seriously,” which at the time was important to me. I was nervous about the ball. I was nervous about my relationship. My then-boyfriend had formed so many instant, super-close friendships in law school. I frequently felt left out and wondered if I would be left behind. I desperately wanted to be a part of this part of his life, but I suspected I was never going to feel included no matter how many of his classes I sat in on or how well I got to know his new friends.

I was young and insecure and I thought a beautiful dress could get his friends to like me. This was the wrong goal to set for myself, the wrong approach to take, and, unsurprisingly, it didn’t work. But I didn’t consider the purchase a waste. I did look and feel elegant and pretty at the ball, and it was a lovely evening. Later that year, a friend invited me on short notice to be his plus-one for a black tie wedding, and the gown kept me from scrambling to find something to wear. Last April, I had the chance to pull the dress out from the back of my closet again, for another wedding. I assume the future holds more parties and weddings and chances to slip back into that gown.

In 2016, I produced a group photography show for the regionally popular Instagram account that I created and manage. I channeled much of my stress into shopping for the dress I’d wear to the show. I went to every major clothing store in my area: two big suburban malls, an outdoor outlet center, Nordstrom Rack, Marshalls, and Kohl’s. After one unsuccessful day of shopping, I found myself sitting in my car at Sonic, stress-eating chicken fingers out of a paper bag and a gulping down a frozen cherry limeade, wondering if everyone had this much trouble picking out clothes.

My mom and I went back to the outlet mall and we went into a store I’d skipped on my first trip. She pointed to a black dress on a hanger and asked what I thought of it. I wear a lot of black, so I’d originally wanted to find something more out of my comfort zone — but, despite the color, the dress was not at all something I would wear. It had very tiny holes cut around the waist where, if you looked close enough, you could see my bare skin. The length was a few more inches above the knee than I’m typically comfortable wearing. The dress had a choker built into its neckline. I was certain I was not a choker person, but I tried the dress on anyway.

I liked it, and it was $45 and I was very ready to quit shopping, so I bought the dress even though I was unsure about the choker. I thought maybe I would cut the choker off or slip my head in front of it, but on the day of the event I went ahead and wore the dress as intended. The choker elevated what would normally be a fairly pedestrian black dress into something a little more unique. The dress was, for that one event, exactly what I wanted. I felt confident and happy at the show. In all of the photos taken of me that night, I’m smiling as widely as I ever have.

I recently sold the dress to consignment because I was sure I’d never wear it again. I hope it conjures up the same confidence in the person who bought it.

Sometime in the last few years, it suddenly seemed impossible to find shirts that didn’t have part of the sleeves missing near the shoulders. One day I was at Loft and saw a plain black shirt with a high neckline and buttons in the back. I liked the fabric and the shape, despite the weird shoulders, and it was $20 so I tried it on even though I felt sure “cold shoulder” tops were not my style. To my surprise, the shirt came home with me.

I first wore the shirt on my 27th birthday, paired with a long gold costume necklace that had belonged to my grandmother. I didn’t worry about looking too trendy or too dressed up or too much, I just enjoyed playing arcade games with my friends and eating Korean tacos.

A few months ago, I bought myself, of all things, a diamond necklace on a gold chain. It felt like the most ridiculous thing I could ever buy. I am not the kind of person who cares much about diamonds. All of my other jewelry is silver. I never thought I wanted jewelry this nice, never saw the point. Could I even be trusted with such a thing, or would I tangle it into a knot or leave it behind at the gym?

I wanted the necklace because I’d told myself that, once I submitted my final student loan payment, I would buy myself an out-of-character present. I could think of nothing more out-of-character than a diamond. The necklace is small and understated and it cost nearly $300. Anything I own that even approaches that cost came to me by way of coupons or sales or as a present. I never I buy anything expensive for myself because I feel guilty buying myself anything, especially if it’s pricey or frivolous. After I saw the ad for the necklace and felt drawn to its tiny star shape and imagined how it might look dangling from my neck, I heard that familiar internal voice telling me you don’t deserve this, this is too much for you.

That’s when I knew I needed to enter my credit card information into the jeweler’s website. I wanted to get the necklace as a tangible reminder that it’s okay to want something only because it’s pretty, and it’s fine if it serves no other function.

Last month, I bought a dress from a little local boutique I’d previously assumed was “too cool” for me. It’s a sleeveless knit dress with a ruffled top, a pleated skirt, and color blocks of navy blue, salmon, mustard yellow, and red. I got it on sale for $59.99 (marked down from $89.99). I was shopping with a friend who was visiting from overseas and when I touched the hem of the dress, she encouraged me to try it on. I loved how it looked on the hanger but was certain it wouldn’t be right on me — it was too eye-catching, too form-fitting.

When I bought the dress, I was buying the promise that I can be the kind of person who is unafraid to stand out from the crowd by wearing something so unique and showy. The dress will be good to wear while walking the boardwalk at night, attending art openings, and sipping fancy cocktails in hip bars. I was also buying the promise that I will have that kind of summer. And maybe I will.

I know I sometimes make things difficult for myself, but ultimately I think my shopping process works for me. Besides, if I stopped approaching shopping the way I do, would I also stop caring so deeply for the items folded in my dresser?

My pickiness prevents me from having an overly abundant closet that requires constant reorganizing and weeding. I still have more than plenty to wear. I only own things that I really like, that work with other things I own, that I’ll wear until they completely fall apart — and that’s a promise I know my clothing can keep.

Kerri Sullivan is a writer from New Jersey. She writes one personal essay every month for her TinyLetter. 

This story is part of The Billfold’s Clothing Series.

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