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What to Wear? The Theory Behind Choosing Clothes

A woman once told me that the essence of style lies in simple cuts and interesting patterns. At the time, as a fashion novice, I took her word for it and tried to buy shirts and dresses in classic shapes that had a little more pizzazz in the fabric. Lately though, I’ve been wondering how exactly she came to that conclusion, and is it a universal truth? And furthermore, is fashion a frivolous study in “looking good”? Or is it something more?

This week I looked at how my friends dress themselves and why they choose to wear what they do. I realized that clothing choices can be used as a way to express ourselves, portray an aspect of our personality, feel comfortable, feel close to someone, or help ourselves be functional in a specific environment.

The other day, when my professor walked into class, her clothing immediately drew my eye – not because it was particularly vibrant or unusual, but because her choices flowed together so cohesively. She was wearing pink corduroys with a red and white, vertically-striped shirt, a  cardigan, and tan shoes. The range of pink hues created an overall effect such that each piece of the outfit was very much connected to the others. I approached her after class, explained this article, and asked her about her thought process. She seemed taken aback! I was expecting to hear that she was wearing her favorite color, or wishing for something lighter during our stormy weather. But instead, her very practical answer was that she owns a limited number of pants, and what goes, goes! I would extrapolate her response to be that for her, the focus while choosing her clothes for the day is not necessarily on expressing a mood or feeling, but rather to feel comfortable, functional, and professional in her work environment.


Here’s my friend Melinda. I loved the combination of her scarlet shirt and dark red jacket, and was reminded of my professor’s monochromatic outfit! I asked her how she made this choice: was she trying to express something? But similarly to my professor, for Melinda, it also came down to function! Having already chosen the red shirt without a specific reason in mind, she chose the jacket without its color in mind, but only for its warmth! This emphasis on function does not deter me in my investigation of personal style. Instead, I feel encouraged! Clothing is clearly not just about appearances. In many cases, we are forced to choose between an outfit that is functional versus stylish. But it’s clear here that function and style don’t have to be mutually exclusive!


Pictured here are Annie (left) and Molly ( right), modeling two very different sets of clothing. Annie’s outfit is very typical of her personal style, while Molly’s is a slight deviation. I’ll first note that Molly chose to wear sweatpants out of necessity, due to an injury. But rather than be deterred by what some might view as a wrench in her planned outfit, Molly decided to capitalize on the colors and high waist of the pants by pairing them with a black crop top and lavender bralette. In this moment, Molly had two goals: feel comfortable and feel confident, and she was able to accomplish both by carefully considering the articles of clothing she would put on her body. Annie often wears outfits similar to the one she is pictured wearing here. While not apparent in this photo, the fabric of her shirt was thicker than most and slightly textured. The qualities of this fabric, along with the shirt’s uneven hem, add flair to an otherwise standard tank top, and you might have to take a moment to look a little closer in order to notice. This dynamic expresses an aspect of Annie’s personality very well: while relatively soft-spoken upon first meeting someone, she reveals, upon closer inspection, a strong, complex, and hilarious personality.


This is a photograph of my brother, James. For him, clothing choices are all about feeling confident without breaking the bank. He does his shopping almost exclusively at thrift shops, rather than shelling out cash for over-priced name brand clothes that will probably wear out in a year anyways. We found this sweater and pair of sunglasses in a consignment shop, and he immediately put them on. The drape of this sweater and the winged shape of the glasses show his confidence and the pizzazz of his personality.


I could put a hundred photos and tell a thousand stories in this article, and there would still be a million more unique examples of why people wear what they wear. For me, a lot of my clothing represents connection to other people. I’ll wear the jean jacket my big sister handed down to me, or the scarf my dad gave me for Christmas, or a dress my mom and I picked out together, and the reminder of someone I care about helps me feel confident and ready to take on the day. And that’s what I think it comes down to: wearing the clothes that help you feel the most like yourself, the most honest, and the most comfortable in your own skin.

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