Editor’s letter: Why I finally said yes to the dress

The year was 1999, and I was discussing my forthcoming wedding plans with a close friend. When the subject turned to what to wear, she blurted out, ‘Don’t wear a bloody suit!’ I had to laugh. Firstly: of course, if you want to wear a suit on your wedding day, that is your (very chic, I might add) business. But she said it because by this time in my life, aged 29, no one had seen me in anything but trousers for a good 20 years. She argued – strenuously – that I should wear something incredibly special. In my case, that meant a dress, for the first time in decades.

We don’t need a psychologist to trace my fear of dresses. From the age of about 11, I was repeatedly told by friends that my legs were ‘too skinny’, unattractive. There was one day, in 1994, when I dared to wear an above-the-knee pencil skirt and a homeless man shouted ‘chicken legs!’ at me across a busy high street. I spent the rest of the day desperate for the first chance to retreat back into my baggy jeans.

It seems so strange, I know, but I genuinely believed that dresses were not for the likes of me: reedy (bony?) women with no curves. Frankly, I didn’t feel feminine enough for the business of pulling them off. So my friend was right to think I’d walk up the aisle in my trademark look of wearing a suit. In fairness, I’d amassed a pretty fancy arsenal of them. I told myself I was channelling Bianca Jagger in her white wedding suit, or Marlene Dietrich rocking the hell out of a satin tux. But it was mostly about making sure no one ever saw a sliver of my legs.

For the record, I wore a maxi skirt for my wedding. You may be surprised to know that it was a succession of achingly cool fashion-editor colleagues who, over the years, rehabilitated my body image. The turning point was in 2003 when a stylist friend all but put a gun to my head to make me wear a dress to a black-tie dinner. Designed by Dolce & Gabbana, it was corseted, black, satin, skintight – an absolutely textbook slice of Italian va-va voom and the sort of thing that usually I’d run from, screaming. But as it covered my knees, I relented, and headed out feeling all the confidence of someone about to sail the ocean on a plank of wood.

I discovered something transformative: you don’t need to feel ultra-feminine to wear the dress. The dress will do that for you. The compliments I received that night were different to any I’d ever had. It changed my entire wardrobe but, more importantly, my self-confidence. To this day, I still probably reach more for trousers than skirts or dresses (old habits die hard). Which is why it never fails to amaze me that, when I do wear a dress, how differently people* treat me. Rightly or wrongly, I am addressed with more respect. I am smiled at more. Taxi drivers are nicer to me. My husband compliments me (if you follow me on Instagram, you’ll understand the significance of this). I feel polished and put together and always prettier when I’m wearing a dress. So sue me for enjoying that once in a while!

Here, we celebrate some of the most iconic party dresses that have really stood the test of time because they give the wearer the superpower of confidence, something we all deserve. If for some reason you too have feared stepping into that power, I can safely tell you from experience, you won’t regret it.

*OK, men

Editor’s picks

A few things I’m coveting this week

earrings

Edgy glamour for your ears. Earrings, £38, oliverbonas.com

shoes

Who says you can’t be chic and comfortable? Shoes, £225, katespade.co.uk

shirt

These ruffles really pop. Shirt, £115, Alex Mill, net-a-porter.com