I have a confession. I haven’t always been completely honest.

I fess up to almost everything: which fashions I think we should borrow from and which I think we should ignore; what I have learned from my own outfits that worked and what I have learned from those that didn’t. The bit that I have sometimes fudged is that when I have these conversations in my head, they focus more on the degree to which clothes are or are not flattering than ends up on the page. I filter it out from what I say out loud.

Now, there are good reasons for this. Whether or not they are flattering is the least interesting, most reductive way to talk about clothes. Spending the whole time craning over your shoulder to critique your back view in the mirror is the quickest way to suck the joy out of fashion. Also, the internal logic that tells me I “can’t” wear a short skirt doesn’t mean that someone else can’t wear one. Setting stupid rules in my head for myself is stupid enough – but setting stupid rules in my head for other people is a stupid step too far.

So, anyway, today I sat down to write about cropped trousers and I thought, well, obviously it’s about getting the right combination of trouser width and heel height so that your ankles look OK. Then I thought, I can’t write that! Ankles hinge your feet to your legs, enabling you to walk. Any ankle that does that is a top-notch ankle. Which is true. But it is also true that most of us would rather look like Audrey Hepburn than like Oliver Twist while baring our ankles in short trousers.

What I wore this week: an asymmetric skirt Read more

There is always an easy way to get an elegant line, which is by wearing very high heels with everything, but I don’t think a cropped-trouser day is usually a four-inch-heel day, so I try not to cheat. A cropped-trouser day is probably a relaxed day when you want to mooch about on foot. So without hoicking yourself on mega-heels, the best cropped-trouser strategy is to pair slim trousers with relatively dainty flats (a slender loafer is your modern version of a ballerina pump here) or to team wide trousers, like the ones I’m wearing here, with a modest block heel. (A chunky two-inch heel is infinitely more comfortable than a skinny one of the same height.) A bold, wide-legged trouser with a meek shoe looks unfinished, as if you have been caught in beta commute-footwear and have your proper shoes in your bag; a slim capri pant with chunky shoes is a bit 90s girl band. Not that there’s anything wrong with 90s girl band as a look. I’d just rather go with Audrey, if I’m being honest.

• Jess wears trousers, £49, and mules, £59, both topshop.com. Blouse, £315, by Caron Callahan, from couvertureandthegarbstore.com.

Styling: Melanie Wilkinson. Hair and makeup: Samantha Cooper at Carol Hayes Management.

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