How to add a little fashion whimsy without going full costume

I bought a silk-and-lace skirt on a Tuesday, having watched enough women drift past in one to assume the skirt did the drifting. I put it on with the blouse I’d planned, then the little gold earrings, then a cardigan for balance, and the mirror delivered its verdict: governess. And mind you, it wasn't even an interesting-looking governess. It was more the sort who alphabetises the linen cupboard. The skirt came off. It spent the week on its hanger, looking smug and faintly like a petticoat that had escaped the wash. 

The problem, I eventually realised, was arithmetic.

One panel of lace is a personality. A lace skirt, lace top, and lace gloves are a doily with a mortgage. A cherry bag is charming, but add cherry earrings, cherry sandals, and a cherry blouse, and suddenly you are less fashionable, and more of a fruit bowl.

Whimsy never really fails because one individual element is ugly, but rather because there are too many elements that got invited. The trick is to give the silly piece a stern opponent. My lace skirt now gets a man's grey knit and Kolhapuri chappals. One pair of jhumkas goes with a crisp white shirt, and nothing else is allowed to join in. The outfit needs one person making jokes and one person telling them to behave.

This is also why the easiest way into whimsy is through accessories. A bag can misbehave without taking the entire outfit down with it. A tiny top-handle, an embroidered pouch, a charm swinging off a zip: perfectly respectable clothes suddenly have a subplot. Black coat, sensible trousers, slightly absurd bag. The bag gets to be the interesting one. Then go smaller. A scrap of mirror work on a cuff. A ridiculous brooch. A shoe with an unexpected buckle. One detail is enough to make an outfit feel as though it has a secret.

The same logic applies to colour. You don't need to dress like a paintbox had a nervous breakdown. Take one impossible shade, tomato red, marigold, the sort of pink that refuses to be subtle and put it against something quiet. The colour gets to have its moment without dragging six of its friends along. Indian clothes have understood this forever: a sari can be an entire conversation in itself, so the rest of the outfit often knows when to stop talking. Borrow the confidence, not necessarily the sari.

Then comes the slightly wrong thing, which is usually the thing that makes the outfit. A romantic blouse under an oversized leather jacket. Pearls with an old T-shirt. A pretty skirt with something chunky and thoroughly uninterested in being pretty. A sari with sneakers, which the internet has decided is a crisis and I have decided is lunch. The point isn't to make an outfit "edgy". I would like edgy to retire for six months to think about what it has done. The point is friction. Something soft beside something severe. Something precious next to something that looks as though it has survived a minor accident.

There is a useful rule here: if the item makes you look like a different character, pair it with something that reminds everyone who you are. A bow blouse can handle jeans. A full skirt can handle a plain T-shirt. Mary Jane shoes can survive trousers. A floral dress can take a giant leather bag. The more theatrical the item, the more ordinary its companion should be. You are not trying to become whimsical. You are simply letting one thing misbehave.

And please, for the love of dressing rooms, don't match the whimsy. This is where things go wrong. A pearl necklace with pearl earrings and pearl shoes is not a point of view; it is a group project. If your bag has cherries, resist the cherry earrings. If your skirt is covered in flowers, perhaps the floral blouse can stay home. If the shoe is doing something strange, let the shoe do it alone. Whimsy works best when it looks accidental, even when you have spent seven minutes deliberately making it happen.

Now age has very little to do with it. The best wardrobes don't look like someone has gone shopping for a personality every season. They look accumulated. The brooch belonged to somebody. The shoes came from a shop you can still picture. The embroidered lemons were bought because they were lemons. There is something much more charming about an object that seems to have wandered into an outfit than one that was purchased as part of a complete "look".

So don't buy an entirely new wardrobe. Find the one thing you already own that feels slightly ridiculous and wear it with something boring. Let it be the only strange thing at dinner. Let somebody notice it and ask where you found it. Give them a story, even if the story is that you saw it, wanted it and briefly lost all sense.

Lead image: IMDb

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