Personal Style Starts with Confidence (and a Great Red Lipstick)

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Confidence has always been an elusive thing for me. I try to project it, but it is more a fabrication than a true reflection of my state of mind. In all things, I care too much what other people think of me. The smallest of criticisms is often enough to send me reeling for days. I aim to please, even as I try not to. It's a constant battle between the self-assuredness I wish I had and the occasionally crippling insecurity that grips me.

My friends, many of whom are older than I, promise that a brighter, more confident future is just around the corner, that my 30s will be different. At 30, they tell me, What Other People Think will fall away and I'll be left with whatever the hell it is that is left when that goes away. Regardless, they promise, it will get better.

I hope they're right.

I remember being sixteen and thinking that the emotional turmoil I was experiencing then would never pass. I barely believed my mother's sympathetic assurances that being a teenager was a unique kind of torture, but that indeed, it would get better. Similarly, all through our 20s my friends and I have wondered, will it always be like this? Will we always feel strangled by this persistent sense of self-doubt? Will we always be afraid of WOPT (What Other People Think)?

Finally (finally!) I am beginning to believe that I won't be. I'm still a few years shy of 30, but recently I have felt different. Lighter. As if some of that weight of all the expectations and judgments of other people (real and imaginary) has slipped off my shoulders like a fine silk shawl.

And while this newfound freedom (because really, that's what it is) has had impacts on everything from my writing to my relationships, it has also noticably changed the way I approach fashion and beauty. I have always loved fashion, but I have spent my 20s struggling to find my own personal style while simultaneously burdened by WOPT. I'd want to wear red lipstick, for instance, but I could never find that perfect color. Deep down, however, I know it was because I was afraid of the stares, the attention, the criticism that such a "display" would elicit.

"Who does she think she is, wearing that on her face?" went my inner critic. "She looks like a clown!" I'd see myself through other people's eyes. I'd see my mother, who never wears bright make-up, tsk-tsk-ing my choice. I'd see the raised eyebrows of my friends and the rolling eyes of strangers. So what if so-and-so looked amazing with red lipstick? She could pull it off. Not me.

So I'd put the pretty red lipstick down and move on to my "safer" colors, a sea of still pretty, but blend-in-with-the-crowd muaves and pinks. Only then, after I was wrapped in the embrace of decisions, of a look, that would leave me free from potential judgment and criticism, could I feel some version of confident.

(That right there is just sad, is it not?)

With clothes I've always been a bit more bold, perhaps in part because my mother always encouraged me to be playful with clothes, but in the minimalistic 90s, an overly made-up woman was an object of scorn and derision. But even with clothing, I default to the safer choices. I don't show my legs (and haven't since a close male friend jokingly pointed out how pale they are: "You're blinding me, Nina. Cover 'em up!"). I feel uncomfortable with accessories or with clothing that is overtly sexy (thanks, post-motherhood body!). And even when I muster the courage to wear something a bit unconventional, I find myself uncomfortable while I'm out. I hide under a big coat. I wonder WOPT.

But it's a new year and, for so many different reasons, I suddenly care so much less. I feel newly self-confident and oddly bored with all my previously gripping insecurities. I've ordered those solid teal tights I've always wanted but could never picture myself ever actually wearing in public. I found a great (if not the perfect) red lipstick, and I actually wear it. It's still pretty cold here, but I've promised myself that my poor legs will see the light of day this spring. And big coats? They're for warmth, not to hide under.

And suddenly, getting ready for the day is so much more fun than it ever was. I feel inspired by fashion in a way that I never have. I feel genuine and authentic and strong. It kind of rocks, to be honest.

Here are a few other women whose style philosophy and courage with fashion inspire me:

Tavi of Style Rookie: She's only 13 years old and already making waves in the fashion world, and for good reason. Unlike me at 13 (or 26), she dresses with courage and a real sense of fun, with a bit of rebellious teenager mixed in, of course. She writes:

Weirdly enough, it's when people anywhere-outside, in school, online-don't understand my outfits or style that motivates me to just be stranger. Not that I think I'm Bob Dylan or some type of ENIGMATIC ARTISTE or an artist at all, but this refusal of others to try and understand why somebody dresses a certain way (for which the real reasons are, in the end, nothing complex) just makes me want to dress more obnoxiously. Be more difficult to understand, more over their heads.

Or, I'm a malicious and spiteful teenager!

But really, I love it when I love my outfit and I walk from class to class and feel like I'm practically floating. My head is bobbing around like Bjork's when she walked for Jean Paul Gaultier and I just feel very confident in myself, not because I think other people will like my outfit but just because I do. And maybe even because I know other people won't like it because it isolates me and I can be in my own world for a bit. And it makes me feel good, and being creative makes me feel good.

Sally McGraw of Already Pretty: Sally offers a refreshingly empowering perspective on personal style. She writes: "Never let anyone shame you about how much or little you invest in your appearance. It is all about choices, and those choices are yours."

(Amen to that!)

Michelle Obama (of course!) as featured on Mrs. O: Yes, she has access to the best designers, but I do admire our First Lady's confident personal style. Criticisms of her ubiquitious cardigans, statement-making belts and bare arms fall on deaf ears because, seriously, who died and made you queen of her closet? But there are those who find Mrs. O's fashion choices less than authentic. Mrs T, the author of Mrs. O, sharply disagrees:

The other vexing bits of the piece are in the details. Phrases like, "Flotus Tactical Cardigan Collection at J.Crew" and "strategically worn plebe numbers from Target and Talbots" rubbed me the wrong way. I recall a piece Ms. Horyn wrote in April about the value of mixing carefully chosen pieces from Michael Kors and Topshop into one's wardrobe, and another piece that sang the praises of Norma Kamali's collection for Walmart. So why are the first lady's choice suddenly "strategically worn plebe numbers"? What happened to the high-low mix and why can't it apply to Mrs. O?

What about you? Are you afraid to have fun with fashion for fear of WOPT? Or are you, like, so over that?

Nina Moon also blogs at Sweet Disarray.

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