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Your Winter Layering Guide Made Easy

Smart, flattering ways to stay warm and look polished this season

Winter is on our doorstep, and while some of us greet it with a collective ugh, others welcome the cooler weather as a chance to refresh our wardrobes. After all, getting dressed becomes a little more interesting when it’s not just a top and jeans on repeat.

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Cooler mornings and evenings open the door to layering. It creates an opportunity to add a little more fun, depth and texture to everyday outfits without having to buy something new. Regardless of what we do and don’t already have in our wardrobe, after a long summer, sometimes we need a little inspiration as to how to layer up in a ‘chic’ way and not just revert to activewear and puffer jackets.

Trinny Woodall walking in london - winter layer outfit
Trinny Woodall is the perfect muse for unexpected layering inspiration. (Credit: Getty)

Feeling stuck? From knee-high boots to clever layering combinations – think vests over knits or roll-necks under shirts – these simple styling tweaks will help you feel warm, confident and effortlessly put together all season long.

Double up

When it comes to winter dressing, versatility is key. And the good news? Some of your summer staples can work harder than you think.

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Ribbed tanks, for example, don’t need to be packed away. Layer them over a fitted long-sleeve top for a modern, on-trend look. You can also double up T-shirts in contrasting tones or add a rollneck under a knit for extra warmth on chilly mornings.

It’s a simple way to refresh pieces you already own, and it means less time worrying about outerwear pulling the whole look together.

(Credit: Black Pepper,Getty)

Black Pepper Darcey Long Line Jacket , $199

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Black Pepper Elita Knitwear, $139

Hidden benefits

Some of the best layering pieces are the ones you might overlook. Take dresses, for example – just because the temperature drops doesn’t mean they need to stay in the wardrobe.

For dressier occasions, layer a long-sleeve top underneath a shirt dress, add tights and finish with a knee-high boot. Top it off with a tailored coat and you’ll stay warmer than you expect, without sacrificing style.

It’s not a completely new way to wear dresses in winter, but it’s a great reminder that staying warm doesn’t always mean piling on heavy layers.

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Black Pepper Winter Campaign model and Anna Wintor in red coat
(Credit: Black Pepper, Getty)

Black Pepper Cordeen Dress, $149

Swap your scarf for a knit draped over your shoulders. It’s a simple, fashion-forward way to add warmth, without buying anything new. These lightweight styles from Black Pepper are ideal.

(Credit: Getty, Black Pepper)

Black Pepper Talita Top, $79.99

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Black Pepper Pheby Knitwear, $119

Sharp collars

A crisp collared shirt is a wardrobe staple but in winter, it can feel like there’s only one way to wear it.

To give it a fresh update, try layering a second shirt over the top. It creates visual interest through the neckline, adds warmth and still feels light enough to wear under a coat or knitted vest. Stick to tonal shades for a more polished look, or experiment with contrast for something a little bolder. Either way, it’s an easy styling trick that makes a classic piece feel new again.

Street style person wearing layered shirt and suit. Black Pepper model
(Credit: Getty, Black Pepper)
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Black Pepper Eboney Knit Vest, $119

Black Pepper Celine Shirt, $99.99

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