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Caroline Issa: On the trail of a modern street-style star

Want to introduce more colour and print in your wardrobe, but not sure how? Anna Murphy, fashion director of The Times and author of How Not To Wear Black: Find Your Style, Create Your Forever Wardrobe, to the rescue.

Caroline Issa talks street-style, her exclusive Label/Mix collection, and Gogglebox.

Caroline Issa has been grabbing the attention of photographers for years with her individual and polished personal style. Director of indie Tank Magazine and editor of, the street style favourite is now lending her magic to Label/Mix with an exclusive collection.

Eleven years ago, Issa was rushing around during Paris Fashion Week when photographer Tommy Ton captured a picture of her outfit, marking the beginnings of street style as we know it and propelling Issa on her unexpected journey from fashion editor to street-style sensation. “I remember Tommy Ton’s website, there were just pictures of us editors. I remember wearing a Meadham Kirchhoff denim jacket,” says Issa, “It’s been incredible to see how street style has brought so many of us who were behind the scenes to the forefront.”

So how to go about brightening up your wardrobe? The simplest option is to start with accessories, of course – a popping bag or pair of shoes. Or to wear one piece of bright clothing, with everything else dialled down. Yet experimenting with a more head-to-toe approach will bring you bang up to date.

Again, sounds tricky to pull off. Yet I promise that once you start you won’t want to stop. Getting dressed – not to mention going shopping – becomes so much fun. Here are some ideas to get you going.

Team tone on tone

The so-called tone-on-tone approach is a favourite with the fashion pack. Basically, it’s about wearing two related shades, so perhaps contrasting blues or greens, or pink and red, or as here, lilac and red. Grow your confidence by starting with a single item that unites the two shades, like this coat, then build up the rest of your outfit from there.

Opt for a printed piece that does the clashing for you 

Another solo piece that does the heavy lifting for you, even more so, in fact, in that this fabulous frock not only unites colours but patterns too. Clash-matching prints look right here, right now. Again, once you have built your confidence, you can try it for yourself with different separates. Sticking within a particular type of print – like a floral or a check – makes a multi-piece ensemble sing.

Layer a statement print over staples

Introducing the button-through dress over jeans or trousers and a tee or sleek knit. I call it 21st-century layering, and it’s the ultimate moderniser. That’s probably why the front row loves it. And then there’s the fact that this more imaginative approach to mixing and matching makes your wardrobe work harder for you. Wear your dress as just that, or layer it up so that it transforms into – er – let’s call it the “drop”, part dress, part top. Add in a contrast shoe – another favourite FROW move – as a finishing touch.

Embrace vibrant accessories

More game-changer heels, and an even more look-at-me bag. Because you do want to be looked at, honest. And what you never ever want to present as – especially as you get older – is dull. That’s why you need to embrace what I call “mad-on’s” – just crazy enough flourishes that keep you looking fresh. Like this clutch.

As for this tailored two-piece, there’s so much I love about it. There’s the fabric for starters: presents as classic at first glance but, on closer inspection, has some interest-endowing colour running through it. Then there’s the cut. Forget your run-of-the-mill trouser suit. Introducing the trench-plus-trews. It actually makes perfect sense. No need to struggle fitting a top layer over your tailored jacket when you’re en route to the office, because one item does both jobs. And then who wants to wear a jacket at their desk all day? Better to remove it and reveal a pretty – and comfy – silky top. I have gone for a contrast polka-dot that picks up some of the colours in the tweed...

Unite different prints with a common colour 

...Because that’s the other contemporary approach pattern: go for two contrasting genres, and pull them together courtesy of a unifying colour scheme. Cue another very clever dress, which conjures a polka-dot and a floral into one on-the-money item. I love to wear a floaty frock with dressy heels, but I love even more to wear it with some box-fresh white sneakers. It’s one more smart trick that will get you twice as much wear out of your wardrobe. A wedding, a playground: this is a dress that – depending on your footwear – can do both. Increasingly I am taking a two-handed approach to my arm candy, too, for Monday to Friday. One small cross-body or clutch plus one tote means you are ready for whatever the day brings.

Smarten up with graphic patterns

What is it with side-stripe trousers? Well, for one thing they are the ultimate leg lengthener and slimmer, drawing the eye towards your vertical lines, and thus diverting attention from those pesky – how shall I put this? – horizontals that most of us fret about. These are trews that just look effortlessly cool. Likewise with this re-tool of the tie-neck blouse. The vibrant palette, a soupçon of transparency, and – behold! – a style that might once have been fusty becomes something else entirely, while not losing any of its ability to flatter.  

As for the shoes, animal print is going nowhere because it’s another one-stop look-lifter, not to mention youth-endower. I love this new-season twist in fuchsia, all the more so because, worn with the blouse, I look instantly pulled together. The key these days is not to look matchy-matchy – that’s ageing – but to look what I call matchy-non-matchy. Pink check + pink leopard = job done.

Anna Murphy is fashion director of The Times and author of How Not To Wear Black: Find Your Style, Create Your Forever Wardrobe (£16.99, Dorling Kindersley)

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