Years ago, when I was staying in New York with friends, I complimented one of them on her enviably eccentric style. She was appalled. Quirky? She thought she’d been doing Killer Executive.

It works the other way too – all those women whose solution to free-spirit hippy chic is to empty the stores on Sloane Street; the women who ramp up the sex factor so much they end up scaring the bejesus out of most men; the women who assume that, if they assemble the wardrobe of a 17-year-old, they’ll look like a 17-year-old.

Men get it wrong, too. All the time. It’s not easy to see ourselves as others see us and, frankly, sometimes it’s probably best not to. You don’t want to be an open book all the time. However, there are situations when it’s best to play with a straight bat and send out a clear message about who you are. For instance…

The interview

Obviously requirements vary wildly. The more conservative the workplace, the easier it is – go for a great suit (not necessarily matching) in a versatile colour, or a tailored dress. It gets trickier with more creative jobs, but the ground rules are the same. Good-quality classics are universally appreciated and you can semaphore your style credentials by ramping up the accessories as required. Fashion’s obsession with shoes comes into its own here – wear the straightest of suits with a pair of statement heels and you’ll score points in the most design-conscious environments (and if you’ve overestimated the grooviness of prospective employers, you can always tuck your fashion moment out of sight under a desk).

The hot date

The temptation with first dates – as with first novels, first albums and first babies – is to channel every idea, whim and theory you’ve ever had into action. Relax. You really don’t have to put it all out there in one hit. Accessible but aspirational has to be the ideal combination, surely? While you’re at it, something that makes it clear that your dream night out is not a trip to that great little cinema that’s still showing Lesbian Vampire Killers, without having to spell it out, would presumably be handy, so choose from the sophisticated end of your wardrobe. And although you’d be insane not to want to present your best side, you don’t want to be dishonest. A bit of body-consciousness isn’t a bad idea, but needs qualifying – an over-sized tailored jacket over a cut-away vest top or a tight dress should strike the right balance. Men find bondage shoes distracting, and not necessarily in a good way, but if you love them (the shoes, that is), be true to yourself. Most men, poor deluded innocents, say they hate make-up, but what they mean is that they’re not crazy about lots of obvious make-up, unless, of course, that’s what you were wearing when you met, in which case, presumably, you’re their kind of woman. Any suggestion of excessive high maintenance is a turn-off, but this isn’t a fashion faux pas that needs masking, it’s a character defect that needs addressing.

Black tie

One woman’s gala dress is another woman’s choice for putting out the rubbish. Never be frightened to ask the hosts for clarification, although if they’re expecting long, the onus is on them to stipulate it. The LBD is the obvious stand-by, but like all stand-bys, you can probably do better. The right colour gives the simplest dress much more impact. If you’re wedded to black, get yourself some major jewellery and opt for neutral or colourful accessories. If you don’t have an appropriate coat, invest in a cropped jacket instead; they’re easier to find on the high street than a good evening coat and you can wear them in the day with jeans. If you’re on a tight budget, it’s definitely worth checking out vintage sites such as www.atelier-mayer.com for classy bargains – cheap evening dresses tend to look it.

Not black tie (but definitely smart)

Urgh. Oh, for the days of stipulated dress codes... If you’re finding it impossible to gauge what’s expected, but don’t want to end up looking safe and predictable, you’ll find a skirt in a luxurious texture – metallic, tweed, velvet, silk, sequins or any combination thereof – an excellent ally. Then you can either go down the silk T-shirt route, or, if you’re feeling demure, a cashmere sweater. Add some striking shoes, a textured evening bag and one or two show-stopping jewels and you’ve got an outfit that’s both classic and individual.

The school gate

Ah, the tyranny of school-gate chic: no need to go to ridiculous lengths (full make-up and the latest Balmain bondage shoes are not a requirement). However, the little ones can be scarred for life by a mummy who Gets It Wrong – and my, those little ones tend to be conventional. If you’re dropping off on your way to work, then wear whatever that demands (if the other mothers are intimidated, that’s their problem). If you’re not, avoid gym clothes, which mark you out as, a) obsessive, and, b) someone with too much time on their hands. Either way, the others will resent you. Jeans, a pretty but casual dress or skirt combo are all good. Most importantly, run a brush through your hair and remove the sleep from your eyes.

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