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Why everyone should dress like Ellen DeGeneres

I caught up with an ex colleague recently for a glass of wine.

She and I had previously held high-powered jobs in the corporate arena and were now doing different things, living a different life style. I was mostly at home writing, she had joined various top-notch boards and was travelling the world, for fun.

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“It’s really changed my wardrobe” she commented.

“How so?” I asked.

“I threw out all my dresses,” she said.

“I threw out all my high heels” I replied.

We were both wearing jeans and leather jackets and flat boots, and looked pretty good I thought. How liberating it is to really dress the way you want.

While I admire uber stylish women like the Italian fashionista and stylist Giovanna Battaglia and oooh and aah over my daily Maison Valentino instragrams, my style has definitely veered much more towards that of Ellen DeGeneres.

I think she looks fabulous. Relaxed. Appropriate. Herself. It’s a cool uniform. Cashmere v-neck sweaters. Tailored pants. Sneakers. Button down shirts. A tuxedo for night.

Ellen's personal style is perennially comfortable, casual and chic.

Ellen’s personal style is perennially comfortable, casual and chic.

In fact, her uniform is exactly what male designers are wearing when they make their runway appearance at the finale of a show, shows that are often full of tricky, convoluted, expensive and irrelevant clothes for women.

So we have to wear that short-at-the-front, long-at-the-back lurex skirt, with a crop top, shoulder pads and wedge gladiators, but you’re good to go in your grey marle t-shirt and denim jacket?

When I realized I could edit my wardrobe to suit my new lifestyle, the first area I zoned in on was shoes. I’m quite tall, so I never really felt I needed high heels. I have now decided that I will never wear them again.

I know some women say that heels make them feel powerful but to me they have the opposite effect, they make me feel unsure and tentative and off balance, emotions I can unfortunately channel anyway, without the help of a stupid shoe.

Fussy clothing can be swapped fr

Fussy clothing can be swapped for simple silhouettes in neutral colours.

I firstly tossed the very high ones, leaving the mid heeled and kitten heeled options for the business meetings that I do need to attend. But my feet had already moved on. The next time I tried to put one on I felt like one of Cinderella’s stepsisters, forcing my hoof painfully into a shoe it did not want to be in.

Then a thought came to me. A chic shift to the middle class hipster left. Designer sneakers.

I have never been a designer sneaker person. I’ve had Converse, Adidas, whatever running shoe was on sale. I’ve never spent big dollars on trainers. But perhaps I was now this person, the designer sneaker customer?

I recall that Marella Agnelli, the 1950’s Italian socialite and one of the most stylish women ever born, wore men’s sweaters, chinos and driving shoes as she got older. I feel like she might have worn a designer sneaker.

1. Adidas Originals Stan Smith sneaker, $130 2. Adidas x Raf Simons, $502.43 3. Burberry, $845 4. Valentino, $1285.12

1. Adidas Originals Stan Smith sneaker, $130 2. Adidas x Raf Simons, $502.43 3. Burberry, $845 4. Valentino, $1285.12

One great thing about being the ex editor of Vogue is that I can call on all my former fashion editors for advice. I sent out the email: “What is the right designer trainer for my age, my personality? Which label indicates what I want to say about who I am at this stage of my life?”

It’s a big question, especially about a trainer.

Gee I love fashion people though. I got an immediate response: “Here is a link to the best 10 sneakers of the season. You could go for a regulation Stan Smith (the white and green version) but I feel you need something that makes more of a statement. I think you need the Raf Simons in palest pink leather ( about $1200) or a brightly coloured Burberry ($900ish) or maybe a Valentino ( don’t ask the price) although I think we’ve moved on from there and that’s not the message you want to send.”

The shoes Kirstie settled on.

The shoes Kirstie settled on.

I found a pair of white leather Prada trainers which I thought were heaven and showed my friend.

“Yes, good choice” she agreed. I mentioned that I probably needed to Scotchguard them, given that they were white leather, hating dirty shoes and all that.

“Oh no” was the response. “Don’t do that. Designer trainers look cooler if they are a bit beaten up.”

Okay. Maybe this dressing like Ellen thing is going to be more complicated than I first thought.

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