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How to dress: sweatshirt and pencil skirt

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'Pencil skirts, which used to be posh, have become more casual; sweatshirts, which used to be casual, have gotten more posh'

You can play this week's fashion game for free. This is one of those Scrabble trends, you see. You just have to take the pieces you've already got in your wardrobe and arrange them in a different way. Enormously satisfying, this, because it addresses that vexing issue: how can it be that, despite having a wardrobe full of clothes, we so often feel we have nothing to wear?

There are certain combinations that we all know work (steak and chips; tailored wool trousers and a silk blouse). And then there are new combinations that used to jar but that we have now all decided to love (see sea salt on puddings). A sweatshirt and a pencil skirt is one of these new combinations.

The reason it works now, when it didn't before, is that both elements have subtly altered their place in our wardrobes in recent years. The pencil skirt, which used to be narrowly constrained to the office and the stuffier reaches of the cocktail circuit, has taken on a looser, sexier personality. The sweatshirt, which used to be strictly gym or sofa wear, has become a statement piece since being adopted by a new generation of Paris fashion designers wishing to semaphore their youthfulness and informality of spirit. To put it another way, pencil skirts, which used to be posh, have become more casual; sweatshirts, which used to be casual, have gotten more posh. The two have inched towards each other and can now meet on common ground.

This is not to say you can just put any two pieces together, like some maddening Scrabble chancer bluffing her way on to a triple-word score. A straight, scratchy, office-basics pencil skirt with a baggy hoodie will make no more sense now than ever. What you need is a new-breed pencil skirt – something a bit slinky, maybe with a split, or a zip, or a print – and a sweatshirt with a precise outline (no sagging elastic on the hips) and some kind of a wink to fashion in the colour or design.

To give you confidence in the two pieces working together, a visual link – such as the gold bits on these two pieces – will help. A dictionary, however, probably won't.

• Jess wears sweatshirt, £29.99, hm.com. Leather skirt, £149, by Per Una, from marksandspencer.com. Heels, £165, russellandbromley.co.uk.

Styling: Melanie Wilkinson. Hair and makeup: Dani Richardson.


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