There is always a trend, or a style in fashion that can be challenging. For some, it’s boho, or ’90s, or overalls in the nightclub bathroom. For me, it’s boots.

I struggle with them. I love them on other people, but whenever I put on a pair I feel lumpen and weird. I saw a young woman in the street yesterday who stopped me in my tracks she looked so fabulous.

She had olive skin and shiny, shiny black hair pulled back in ponytail, red lipstick and a short, white broderie anglaise-frilled dress, very feminine and pretty, worn with heavy brown workman’s boots, and ankle socks.

Masculine combat boots complementing a feminine look beautifully. Photo: Getty

The masculine shoes added the perfect edge to the frothy, girlie dress, it was a masterstroke in styling. If I, however, attempted that particular look, the effect would stop people in their tracks for entirely different reasons – more in a Bette Davis What Ever Happened to Baby Jane way.

Obviously wearing a heavy boot with mini dress is an outfit more suited to the young, but I have issues with any ankle boot. I just can’t wrap my head around the proportions. If I put on a pretty, longer-length dress, my pre-programmed fashion brain immediately says: “Strappy sandal. Maybe an espadrille”.

It just does not go to kooky high-heeled ankle boot, or a Timberland hiking boot or a rugged cowboy boot. But I realise it’s modern to mix things up, so I give it a go in order to look fashionable and up to date – put on a short boot with a dress or a skirt and just feel wrong all day.

I tell myself that it is a look that has noble origins and to remember the suffragettes. But I will catch glimpses of myself throughout the day and am always startled by the lack of ankles. I can do a trainer with a dress quite easily, but the ankle boot is a bridge too far. And don’t get me started with the short boot with a cropped jean thing. It’s the oddest silhouette ever. It just looks like your jeans have shrunk.

I don’t like the look of leggings tucked into boots. Photo: Getty

I do recall wearing boots every day when I lived in Paris: black ankle boots with a low Cuban heel, that I wore with jeans. But that was back in the 1990s and jean cuts were normal. I bought a very expensive pair of Tod’s riding boots in the early 2000s which I still have, but I don’t do dressage, and I hate the look of trousers or leggings tucked in Puss-in-Boots style, so voilà, they are nicely collecting dust in my wardrobe.

I have bought, and then given to charity, so many pairs of short boots that I was going to give up. But I am going to China this month, and have been warned it will be freezing, so I bought a pair of black, flat motorcycle boots, very chic and so heavy they will need their own suitcase.

I have literally no idea what I will wear them with.