As casual as you like

Some people are never knowingly underdressed.

I've written recently about looking good when dressed casually, and how it's not a look I have ever managed. These past few weeks I've been studying those who do indeed manage it.

A while ago, I went away for the weekend with my friend Kelly, who is never knowingly underdressed: she was in DKNY within hours of giving birth. Her casual look is jeans, worn with high-heeled knee-length Prada boots, some sort of frippery blouse - in this case a divine Pringle chiffon puff-sleeve (a big look for summer, be told), which I had to tell her not to buy two of - and, on top, a cropped, slightly puffed jacket.

With the jacket, it is very important that it be short - I've garnered from these people - as it shows how long your legs are and also, rather crucially, doesn't allow for any fat to be concealed, because these people don't have any. It's a very posh (in all senses), slim, lollipop look.

When we went outside, Kelly wore a baseball cap, while I let my very ex pensively coiffed locks fly with the wind until I ended up looking like a neglected English sheepdog. In all ways, my silhouette was very different from hers, and of course the way we were treated at the hotel reflected this.

Kelly piled as much as, if not more than me, on to her plate at breakfast. But while she was flirted with by the chef (it was self-service), when I approached the breakfast bar he said, quite without prompting: "Go on, have sausages and bacon and some of those" - pointing at the cold cuts - "you know you want to." The waitress also tried to clear my plate away before I'd finished, as if, in some small way, to help me. Kelly instilled a slight tremor in the waiting staff, as if they expected nothing less than for her to change seats four times - which she did - in the loungy bit. It was the boots that did it. My pasty shoes were simply not as authoritative, and when I asked for cashew nuts I got almonds. This is what happens when you choose Nike over Prada.

We went out for a walk one morning. As we got back to the hotel, I saw another well-dressed casual girl walking towards us. She, too, had the uniform skinny legs in posh jeans, knee high-heeled boots, and a cropped, slightly puffy jacket with a fur collar. She totally looked through me, but mentally laid a grid reference on Kelly as she scanned her for a "compare and contrast" on labels, shapes and colours. The exchange ended with a rather filthy look at Kelly who, it would appear, had some sort of Extra Feature the other girl didn't.

We are meant to look for similarities in dress as a tribal identifier - a marker that we are among friends. Malheureusement, fashion doesn't always work like that.

Annalisa Barbieri was in fashion PR for five years before going to the Observer to be fashion assistant. She has worked for the Evening Standard and the Times and was one of the fashion editors on the Independent on Sunday for five years, where she wrote the Dear Annie column. She was fishing correspondent of the Independent from 1997-2004.

This article first appeared in the 19 March 2007 issue of the New Statesman, Trident: Why Brown went to war with Labour