Why You Should Dress In Embarrassing Fashions

There’s something to be said about a person who loves a style so much that they go all in. It's refreshing and so encouraging to see someone wearing their personality on their back, and helps you pick up tips on how to embrace your style as you admire them not-too-subtly from across the street. When I went to visit New Orleans last weekend, I was completely charmed by a group of men and women sitting at a brunch table one over from me, sipping on Pimms Cups and decked out in their southern Sunday best. The women had off-the-shoulder sleeves with flowers tumbling down to the hems of their dresses; their red lips and blonde curls portraying every inch of the Southern Belle that this Yankee has romanticized. The men had straw boaters on their heads and pastel bow ties tucked into collars, looking like they were ready to board a steam boat heading down the Mississippi once they finished their Mint Juleps. They all looked so eccentric and out of the ordinary — and absolutely fantastic.

As I leaned back in my chair and smiled in their direction, I thought of how wonderful it would be if everyone dressed like that. Not necessarily in that particular style, but if they dressed as loudly and fully as they wanted to. Everything would be so much more interesting.

But not all of us quite have the courage to do so. And if I’m being completely honest with you, I don’t always have it, either. Which would be surprising to those who know me. I like to dress as though Carey Grant were waiting downstairs for me to go on a date — in full ‘50s skirts that come in cotton candy colors and drop-waist dresses that beg for Victory Curls. Betty Draper would scowl in jealous annoyance at my closet, and I would all but hum with the satisfaction from it.

But… while I love wearing things that an Ethel or a Doris might have worn 50 years back, that doesn’t mean I’m standing in a crowded bus, not feeling my cheeks go pink from all the curious glances in my direction. I get cringy when I notice someone take it all in, and more times than not I have moments where I want to pretend to sneeze and slide off my beret in one smooth move.

It’s hard to stand out, even when you know you look wonderful. And it’s hard to be different from people, even when you know that this is the version of yourself that you like best. I can’t tell you how many times I’ve stood at a bar with a long sleeve dress on and side-eyed the cool girl with skinny jeans and red lips ordering a martini next to me. All in a flash, I get wild and slightly panicky thoughts in my head where I want to change my style but don't know how. Nearly bobbling my drink, I look around the bar wildly and think, "Quick, how do I get this dress off of my body?!" There were some harried split-second moments where I wished I could rush into the bathroom and somehow turn my demure dress into a mini, breaking up with Cary Grant hastily in my head along the way.

Take it from the girl that both loves and feels embarrassed over her determination to wear pillbox hats on her commute to work: It takes choosing yourself over choosing the judgements of people.

But once that red haze lifts, I take a breath and take it all back. I make amends with Cary and put a fresh coat of red on my lips, trying to ignore that pull to blend in. And the thing is, I don’t stick to my style as an effort to stand out. I stick to my style because a good dress makes me ridiculously happy. Like about to tap dance like Fred Astaire happy. Like my heart feels like melting butter on toast happy. To me, style is like an intense love affair. And I think it’s crazy that I would take something like that away from myself just because I caught a girl giving me a bewildered look from across the room.

So instead, I hold my breath and let myself marinate in that awkwardness for a minute or two, before pushing it far away and finally getting ahold of the bartender to order some fizzy drinks.

It can be easy to see a fashion forward person and assume they have all the confidence in the world, and thinking that's what allows them to dress the way they do. They probably live and breathe colors and patterns, and can make something absolutely ridiculous look absolutely amazing. But not you — you don’t have that kind of confidence. You assume that you're just not like that, and that's why you can't wear those suspenders or those chunky sandals you’ve always admired but shied away from.

But that’s not true. Take it from the girl that both loves and feels embarrassed over her determination to wear pillbox hats on her commute to work: It takes choosing yourself over choosing the judgements of people. It's not easy half of the time. But it's worth it all the time.

Images: Author's Own; Giphy