4 Reasons Why Personal Style Should Make You Uncomfortable Sometimes


I’m a big fashion lover, and I tend to get a little ambitious with my style. I’m determined to emulate looks by my favorite models, bloggers and celebrities, and end up wearing outfits that initially make me feel great, but afterwards, make me wonder if I was able to “pull it off” as well as I wanted. I’m too aware of what friends will think of what I’m wearing, and often it’s family or friends who look askance at me and wonder why I like to wear heels when I go shopping when they’d rather go in Uggs.

In college, I would head to campus in skirts and heels, so happy to feel pretty, feminine and confident, and these feelings were only slightly dampened when classmates and friends were like, “So, like, why do you dress up so much for class?” I didn’t stop dressing up but I was much more aware of myself after so many raised eyebrows, and I realized that the reactions of my peers were making me feel so uncomfortable. As a commuter, “going to class” was so much more than rolling out of bed at 7 a.m. and walking to class with my comforter still wrapped around my head, fuzzy slippers glued to my feet. Like high school, it was an event. And I wanted to look nice for it.

A couple years later, I’ve channeled my love for fashion into this small fashion/lifestyle/everything blog, and feel like I’ve finally found not only a place to express my love for fashion and personal style, but an excuse to dress up at all. And I’ve come to realize that I like when wearing what I want makes me feel just a little uncomfortable. Here’s why.

1. I’ve learned not to curb my fashion creativity to blend in with what others are wearing.

Every time there’s an event—whether it’s a family party, dinner out with friends, a girls’ night or something totally casual like going to the movies, I get excited just to put together an outfit to wear. From my mother I hear, “Don’t dress too fancy.” From friends, “You look so dressed up! Where do you think we’re going?” and other niggling comments that have the potential to ruin my sartorial excitement. These comments make me second-guess my penchant to dress up, and I end up feeling a little less confident with what I’m wearing. But thankfully, this happens less and less as I’ve learned to assert my right to wear what I want.

Even though I would undoubtedly be more comfortable copying what my family and peers wear, I feel like I would also be sacrificing my creativity and self-expression. We all know how challenging it can be to stand out and be different; even though we all want to be unique, it’s undeniable that human beings are more comfortable fitting in than being marked as strange. Wearing my own small amount of strange is how I assert my individuality, despite how those closest to me may perceive me. Being uncomfortable has taught me that I’m sort of doing something right by making the choice to dress how I want to.

2. I realized how much other people tend to judge me for what I choose to wear.

I think it’s natural to assume a girl who’s overly dressed up is somehow conceited or full of herself, and this is simply not the case. Like anyone else, I have certain insecurities about my body, but I love my legs and I like to wear things that accentuate them. It makes me feel confident, which makes me act confident. But confidence in women is often seen as narcissism, and perpetuates this idea that flaunting the parts of your body that make you feel good is somehow bad.

I’ve learned to care less about what others may say about me because of what I choose to wear, but it’s definitely unfortunate that others have the power to make me—and all women—feel uncomfortable for being confident.

3. I’ve derived a certain measure of confidence by constantly trying new styles, colors and silhouettes.

For so long, I’ve heard friends and peers say things like “I could never pull off what you’re wearing.” They said these things about printed jeans, flowy kimonos, or drop-waist dresses. I’m saddened that they say these things to me, because I constantly try to assure them that they could totally pull it off if they only tried, which is exactly how I began experimenting with my own personal style. Each time I try to wear something different, it’s usually because I saw it on someone else and tried to “pull it off.”

I also feel doubly sad about my friends’ protestations because they highlight certain so-called “flaws” on their bodies and cite those “problem areas” as reasons they can’t wear certain things, and my assertions that they’re wrong and beautiful and that they can totally rock that look often fall on deaf ears. I definitely have moments of insecurity, thinking that this or that definitely won’t look good on me, but when I try it, I realize that even if it doesn’t look as good as it did on Kendall Jenner, it looks like me. From insecurity and discomfort came assurance and confidence, simply stemming from the fact that I tried different styles and trends.

4. Fashion makes me feel special, and ultimately, that’s what self-expression should do.

Experimenting with fashion allows me to get in touch with different facets of my personality. I used to dress in empire-waist dresses and Mary Jane shoes. That style put me in touch with the super-girly part of my personality, which is definitely a dominant part. Then I went through a phase of studded boots, black leather-embellished leggings and structured tops, which lent me a certain edge and sense of cool. Right now, I’m all about the boho—white lace shirts, kimonos, floral prints, everything—and it makes me feel both romantic and like a free spirit of the 70s. Every time I wear something new and different, I feel special, almost like I’m wearing my personality on the outside, and my tastes are constantly changing to reflect all the facets of my personality. Dressing up makes each day feel special, because I’m able to express myself without filter.

Fashion, for me, isn’t a safe experience. It’s experimental, wholly personal, and should make me feel like I’m stepping out of my comfort zone (and hopefully into some killer heels!).

Lisa Lo Paro
Lisa is a freelance writer and bibliophile living on the outskirts of New York City. She likes 2 a.m. with a good book, takes cream in her coffee and heavily filters her photos. Check out her blog The Most Happy, her Instagram, and Twitter.

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