Breaking fashion rules and loving it

"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 would 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: a pair of high-waisted, cropped, wide-leg jeans.

Vintage-inspired fade, frayed hem, button fly: a mix between mum 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 practised for years.

I have 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.

There were certain things you should and should not 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 1.6m-tall, curvy young woman. I wore columns of dark colour; I obsessed over hemlines to have them at that perfect point to make my legs look long and lean.

If an item did not flatter, it did not enter my closet.

When I turned 40, I started to slowly question my choices, easing up on some of those rules.

I had 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 was surprised by how easily it fitted into my wardrobe.

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 could not wear because I have a large bust.

Some rules I broke out of necessity. After I gave birth to my daughter, I developed plantar fasciitis and could not wear heels. 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 colour, 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 colour are not ugly. And I really found this trend ugly. I could not 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, flats, Birkenstocks and Nikes.

And, yes, my beloved new jeans do look an awful lot like a pair of his jorts, but I do not care. I am dressing for me and it makes me happy.

When I wrongly recommended that woman to 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 is 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 has supported me all these years.

And now I am finally taking my own advice and recognising that I look best when I enjoy what I am wearing.

Sometimes, that is a dress that whittles my waist or a shoe that makes my legs look amazing - and sometimes it is a piece that breaks all the rules.


•The writer is editor of style blog Wardrobe Oxygen.

A version of this article appeared in the print edition of The Sunday Times on November 04, 2018, with the headline 'Breaking fashion rules and loving it'. Print Edition | Subscribe