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Why I gave up on ‘flattering’ clothing

For years, I followed the rules and preached the same on my blog. But then life changed.

The author, enjoying several style no-nos rolled into one. (Courtesy of Alison Gary)
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“What the heck are these?” my husband asked, pulling a piece of clothing from the laundry hamper to toss into the washing machine. “Did you cut up a pair of my jeans?”

In his hands was something I swore I’d never, ever wear. Something that as recently as this spring I instructed one of my blog’s readers to remove from her closet because it was so offensive. The offensive item was a pair of high-waisted, cropped, wide-leg jeans. Vintage-inspired fade, frayed hem, button fly: a mix between mom jeans and culottes.

How did I get here? I have spent my entire life and career meticulously cultivating a look that would elongate, slim, flatter. This garment was the antithesis of all that I have preached and practiced for years.

I’ve had a passion for fashion since I was very young. My mother would scold me for using a whole box of Kleenex and a roll of tape to create dresses for my Barbie dolls. In high school, I was known for my quirky and inventive looks; after college, I got a job in apparel. When I switched to corporate America, I created a fashion advice blog. I read all the books, was a “What Not to Wear” devotee, and totally drank the fashion rules Kool Aid. There were certain things you should and shouldn’t wear to flatter your figure. To flatter meant to create an hourglass shape: Whittle that waist and lengthen those legs.

Not an easy feat for a 5-foot-3 curvy young woman. I wore columns of dark color; I obsessed over hemlines to have them at that perfect point to make my leg look long and lean; I invested in many wide elastic belts, which were worn just below the rib cage to not only make my legs look longer, but to give the appearance that I had a smaller waist. I had a whole drawer full of Spanx and another of pushup bras, and every pair of shoes I owned had at least a three-inch heel. I don’t want to admit how many wrap dresses I’ve purchased over the past decade, and all of them would be in colors appropriate for a winter, a la “Color Me Beautiful,” the famous guide to which colors should be worn by which women, according to their complexions. If it didn’t “flatter,” it didn’t enter my closet.

When I turned 40, I started to slowly question my choices, easing up on some of those hard-and-fast rules. I worked so hard and for so long to fit my shape into the ideal of my Barbies in their Scotch tape-cinched Kleenex dresses. I was exhausted.

So I broke the rules.

It started with an orange sweater that caught my eye in a Gap store window. I went in hoping to find it in a color more fitting for a True Winter, but all they had was the sunny shade. I tried on the orange and ended up purchasing it. I loved the color, and I smiled each time I pulled it out of the drawer and over my head. I was surprised how easily it fit into my wardrobe, complementing my dark denim and providing lively contrast with my cool red lipstick. What’s funny is I got more compliments wearing it than any cobalt blue or emerald green piece in my closet.

I moved on to horizontal stripes, something I was told I couldn’t wear because I have a large bust. The thing is, I had the same size chest whether it was covered in solid black or Breton stripes. I started with one top from J. Crew, and now I have more than a dozen that are regularly worn and loved. I wear stripes so much that I think if a cartoon character were made to represent me she’d be wearing a navy and white striped T-shirt.

Some rules I broke out of necessity. After I gave birth to my daughter, I developed plantar fasciitis and couldn’t wear heels. I tried. Lord, I tried. It went away, and I went back to heels — and then developed a fallen arch. I have now embraced my collection of Birkenstocks, brogues, flats and funky sneakers.

Some rules were easy to break once I got the hang of fashion rule-breaking. Into my closet came chunky sweaters, overalls, midi skirts and plenty of big, bold prints. It was liberating to wear clothing that was fun and for me, not to fit an ideal.

But some rules took longer to break. I was happy and feeling free in any color, bold stripes and flat shoes, but I just could not get on board with the latest trend of wide-leg cropped jeans and pants. The difference? Stripes, flats and an outside-the-box color weren’t . . . ugly. And I really found this trend ugly. There’s nothing else that will make this short, squat body look even more short and squat. It’s why I advised my blog reader to ditch her pair. I couldn’t do ugly. Or could I? It wouldn’t hurt to try …

And now I sit here in wide-leg cropped jeans writing this piece. I saw the trend so much in my Instagram feed that it wore me down. I own three pairs of cropped wide-leg pants and wear them all the time. I wear them with heeled boots, with flats, with Birkenstocks, with my Nikes. And yep, my beloved new jeans do look an awful lot like a pair of my husband’s jorts, but I don’t care. I’m dressing for me, and it makes me happy.

When I wrongly recommended that woman give up her jeans, I did give some good advice:

“ … we are square pegs and a lot of fashion is round holes. We try to shove ourselves into those round holes with compression garments, uncomfortable shoes, and over-shopping thinking there’s that perfect something that will make us suddenly chic. Style comes from within you, not within your closet. You are fabulous just the way you are. You deserve clothing that doesn’t require so much effort and so little payback.”

The older I get, the better a relationship I have with my body. I no longer want to punish it for not fitting an ideal, but pamper it for how well it’s supported me all these years. And now I am finally taking my own advice and recognizing that I look best when I enjoy what I’m wearing. Sometimes that’s a dress that whittles my waist or a shoe that makes my legs look amazing — and sometimes it’s a piece that breaks all the rules.