All hail the shacket, and 20 years of other great (and not so great) outfits

For 20 years, I have been dressing up every week in the look I write about in this column. Today I’m in a shacket, of which more later. I’ve road-tested boilersuits and blouses, prairie collars and pencil skirts. I’ve shoulder-robed, I’ve clutched, I’ve French-tucked, and I’ve worn every hemline – well, so long as it is knee-length or longer, that is. (Funnily enough, I have never in all this time felt compelled to share here my thoughts on bikinis.)

Every week, for 20 years. I won’t do the maths because it makes me feel ancient, but I think you’ll agree that it is time to switch things up a little. So the shacket is my swansong, as it were. I’ll still be here, writing about fashion and style, but I won’t be doing the show-and-tell photograph.

I’m not sure what all these photographs of me in mostly quite silly outfits have contributed to the Guardian’s great legacy, but I know that I’ve learned a lot from being in them. There is nothing like having one’s picture taken for Britain’s best-read quality news outlet in that week’s zeitgeisty look – Rupert Bear trousers, or the Meghan Markle coat, or Miss Marple checks – to focus the mind on how to wear fashion-forward clothes without looking totally ridiculous. I haven’t always succeeded in not looking ridiculous, by any means, but I gained as much fashion wisdom from the weeks when I looked daft as I did from the photos I can look at without wincing. Sometimes you win and sometimes you learn, and all that.

Related: How to wear tobacco, the new neutral | Jess Cartner-Morley

I’ve learned that clothes that are too tight never look good. I’ve learned that a jacket with a well-tailored shoulder is a bit dull but always a good idea, and that simple high black or white court shoes work with almost anything, in any season. I’ve learned that shape matters more than colour or print. I’ve learned that tartan makes me look like a Bay City Roller and not, sadly, like Cher in Clueless. I’ve learned to be open-minded about what I try on, but to trust how I feel when I look myself in the eye in the mirror.

Oh, and today I’ve learned that a shacket – half jacket, half shirt – is a really good idea, despite the silly name. Comfortable but structured, somewhere between Twin Peaks’ Bobby Briggs in his flannel check, and Coco Chanel in her boxy knitted cardigan-jackets. It’s always fun to try something new, right?

On which note, see you next week.

• Jess wears wool overshirt, £169, warehousefashion.com. Other clothes, her own. Styling: Melanie Wilkinson, assisted by Peter Bevan. Hair: Joe Pickering at Carol Hayes Management

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