Top 5 UK Winter Holiday Destinations And How To Dress For Them

Winter can be tough for us all, with Christmas seeming like it was forever ago and spring not yet in touching distance. Coping with the endless darkness and brutally cold weather can feel difficult.

A change of scenery is a great solution to the winter blues, so we’ve rounded up our top five UK winter holiday destinations and paired them with some stylish winter holiday outfit ideas you can take. 

From hiking in the mountains to stunning city sights, make this winter your most stylish and fun one yet.

Table Of Contents

  1. Devon
  2. Edinburgh
  3. York 
  4. Isle of Skye
  5. The Cotswolds


a picturesque sky and trails in Devon

Devon could be the perfect destination for your winter holiday if you’re looking for picture-perfect cottages, cute market squares and stunning coastlines. Home to many Areas of Outstanding Natural Beauty, whether you want a charming city break packed with culture, or a hiking holiday exploring the wilderness of Exmoor and Dartmoor, Devon is a superb choice.

Devon is beautiful all year round but is especially magical in winter when coated with glistening frost. 

South Devon is known for its warmer climes, boasting the English Riviera filled with palm tree-lined shores and the natural suntrap of Torbay, a great place to feel the winter sun on your face. In the east, you’ll find the Jurassic coast, known for its dramatic cliffs, which in winter are great for exploration, rock-pooling and fresh coastal winter walks. 

With abundant National Trust properties and picturesque panoramic views, Devon is the perfect escape to banish the winter blues, whatever your interests!

What to pack for a trip to Devon in winter

Since Devon has so many things to offer, you’ll need a good pair of comfortable walking shoes or hiking boots and a trusty winter coat, as you’ll probably spend most of your time exploring the great outdoors. 

Barbour Storr men’s boots are a versatile choice as they are both practical and stylish, so they would look just as good on a winter hike as they would cosying up in a restaurant after a busy day of adventure. For women, our Barbour Paisley women’s boots are just as effective.  

A women with dark hair wears Parajumpers hooded down coat in khaki

Parajumpers Rindou Women’s Hooded Down Coat 

Parajumpers offer some great quilted jackets for both women and men that will keep you dry and cosy for your winter walks around the stunning Devon coastal paths or exploring the Exmoor wilderness. Don’t forget to visit a tea room when it’s time to thaw out after all that walking (you’ve certainly earned it!).


Edinburgh Castle covered in snow

If winter hiking around the coast doesn’t seem like your thing, why not visit Edinburgh for a charming winter city break? Edinburgh is full of the hustle and bustle during the Christmas months with its German Christmas market and across the New Year holidays for Hogmanay. Once the holiday chaos dies down, Edinburgh can be just as spectacular for a post-Christmas break. 

For a start, Edinburgh Castle (pictured) provides a stunning backdrop when exploring this amazing city. Wander up the Royal Mile for a photo opportunity, or if you’re a culture vulture, pop in to learn more about this stunning historical site.

Or, if shopping’s more your thing, you’ll find many designer shops, including Louis Vuitton, Burberry and Harvey Nichols, just beside the newly established St James Quarter shopping mall filled with various high-end and high-street favourites. 

Take the weight off after a day of hitting the shops by visiting one of Edniburgh’s stunning restaurants, such as The Ivy, then dance the night away enjoying the city’s exceptional nightlife.

What to pack for a trip to Edinburgh in the winter

When packing for Edinburgh, the possibilities are endless, as you can do so many different things. If you plan on hitting the shops, you want to look as stylish as possible without compromising warmth.

Some stylish knitwear is a great, versatile choice that you can pair with jeans, Chelsea boots and a stunning designer handbag like this gorgeous Tommy Hilfiger crossbody bag, to carry your look from the shops to the bars.

Black Tommy Hilfiger sholder bag with gold logo and gold chain

Tommy Hilfiger TH Chic Women’s Crossover


A scenic view of the river Ouse in York against a blue sky

An equally captivating winter city break, York provides the perfect mix of culture, history and entertainment.

Once the Christmas tourism has died down, visiting York post-festive period allows you to explore this amazing city whilst avoiding large numbers of tourists.

Start by walking the ancient walls for stunning city views, and visit Clifford’s Tower, an English Heritage site built by William the Conqueror steeped in history. Then, wander into the city centre and admire York Minster in all of its glory. 

An upwards shot of York Minster covered in snow

Then grab a hot chocolate and stroll around the Shambles for local shopping and artisan products.

With York Dungeons, the Jorvik Viking Centre and York Castle Museum all within walking distance, there won’t be an opportunity to get bored when you visit York, particularly if the winter weather takes a turn! You could even take a riverboat trip or hop on an open-topped bus while planning the day’s activities!

What to pack for a trip to York in the winter 

Because you’ll be spending time outside exploring the city walls, and inside trying out all of the attractions York has to offer, you’ll want to dress accordingly. 

A man poses in a khaki Barbour wax jacket

Barbour Dunlin Men’s Wax Jacket

A Barbour wax jacket is a great pick that will keep you dry and warm when you’re outside, should the weather start to change. Super stylish and versatile, it’ll also look good when you’re enjoying a coffee shop stop to refuel in the middle of the afternoon. Pair yours with jeans or chinos and a fashionable pair of trainers that won’t compromise comfort.

Isle of Skye 

Amazing sunset at the Fairy Pools, Glen Brittle, Isle of Skye, Scotland

One of the most idyllic places in the UK, the Isle of Skye is situated on the west coast of Scotland and is a must for all lovers of the outdoors. Famous for its scenery and landscapes, you won’t be disappointed if you want to photograph the winter sun glistening off the island’s fairy pools, hike in the mountains, or search for the Northern Lights.

Skye is beautiful all year round, but by visiting in the winter months, you’ll have the opportunity to witness glorious sunrises and still take advantage of a decent sleep-in. The sun rises between 8 and 9 am in the winter and sets at 3:30 pm, so there are plenty of opportunities to witness gorgeous pink hues set against a stunning backdrop. 

If you like your whisky, you can visit one (or all!) of three distilleries, including Torabhaig, Rassay and Talisker, the oldest working distillery on the island. Or visit Armadale or Dunvegan castle and gardens to take in some culture. 

With plenty of attractions and restaurants, Skye is the perfect place to escape it all while still enjoying life’s finer things. 

What to pack for a trip to the Isle of Skye in the winter

If you’re heading to Skye, you’re probably looking forward to lots of hill walking and adventure, so you’ll need to ensure you’re warm and comfortable.

A warm beanie hat is a good place to start, followed by a thick winter coat. This Unisex Didriksons Winter Parka is insulating, breathable and waterproof, perfect for walking in the Cuillin mountains. Leggings will allow you to remain comfortable on your hikes, and we’d recommend completing your look with a pair of Timberland Greyfield Women’s Waterproof Boots.  

Timberland black suede boots

Timberland Greyfield Women’s Waterproof Boots

The Cotswolds

Broadway, The Cotswolds in the winter

If The Holiday didn’t convince you, you’d be hard-pressed to find a more beautiful place than the Cotswolds for a UK winter break. If you’re lucky, these ancient towns might even be covered with a layering of snow when you visit, adding to the area’s charm and character.

The Cotswolds runs through five counties and covers almost 800 square miles, leaving much to explore. Each area may have its own unique identity, but the rolling hills and the golden stone of the buildings fill it with Cotswold character.

If you like to hike, you’ll love walking through the Malvern Hills meadows, an Outstanding Natural Beauty area set in Worcestershire. Or maybe you’d prefer to visit Castle Combe in Wiltshire, often called the prettiest village in England, when it doesn’t have as many tourists. 

Marvel at the cobblestone streets and the thatch roof cottages, visit castles and country houses and enjoy the relaxed pace of Cotswold living. 

What to pack for a trip to the Cotswolds in the winter

After a day of exploring, you can’t beat a good meal in a British country pub, and luckily, there’s lots of opportunity for that in the Cotswolds.

Dressing smart-casual will give the appearance of an elevated off-duty look. Think countryside style and pair your Barbour International chequered shirt with jeans, and finish the look with a classic pair of chukka boots.

A man dressed in a Barbour checked shirt

What do you wear on a winter holiday?

What you choose to pack for your winter holiday will depend on the range of activities you have planned when you get there. 

If you’re going on a hiking holiday, prioritise warmth, practicality and comfort, as you don’t want to be hiking up hills in the wrong footwear. Whereas if your holiday is more of a city break, although you’ll still want to be warm, you’ll be able to choose more outfits based on the nature of your activities. Take some smarter clothes, if you’re planning on hitting a fancy restaurant or visiting some swanky bars.

Whatever your destination, the key is planning ahead and only packing stuff you’ll wear. If you can, pack things that you’ll be able to wear more than once, then this will save space in your suitcase or holdall, make it easier to carry and leave room for picking up some memoirs or souvenirs for friends and family.

Shop for your winter destination at CHO

Whichever UK destination you choose, or if you’re going further afield, you’ll find perfect wardrobe staples to take with you by browsing our men’s and women’s clothing and accessories at CHO and shopping the links above. 

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