Winter Getaway Style

With the festive season now a distant memory and the dregs of winter still lingering, it’s easy to find yourself daydreaming of the sun-soaked summer holidays ahead. Of course, if the pressures of the new year are really getting to you, you can choose to take off now, without waiting for the chill to relent.

Whether you’re after a culture-rich European city break or something more exotic, you’ll want to ensure your style is on point. Read on for a lowdown on the essential pieces to pack for some of our favourite winter getaway destinations, from Norway to New South Wales.

Prague, Czech Republic

Prague, Czech Republic

With its historic architecture and quaint cobbled streets, the Czech capital is arguably at its most picturesque in winter, when you can expect a generous flurry of snowflakes to cover the city’s medieval castles, creating a prime Instagram-worthy scene.

Of course, this means you’ll be contending with below zero temperatures so you’ll want to stay layered up for the duration of your trip. Where to start? We’d suggest packing a selection of your favourite knitwear, from roll necks you can layer to chunky cable knits.

Inject some colour into Prague’s wintry setting by opting for knits in rich hues. Whether you team a woollen blood orange jumper with charcoal slim-fit jeans or layer a burgundy sweater under a navy jacket, a shot of colour will instantly liven up your look.

If you’re looking for additional warmth from your legwear, a pair of brushed cotton tailored joggers or some fitted long johns can be worn underneath your favourite jeans.

A tailored woollen overcoat is the perfect choice of outerwear for Prague in the winter, as you’ll be able to layer up underneath while still retaining a sense of refinement. If you’ve taken our advice and plan to opt for a colourful knit, then keep your overcoat neutral – a black, grey or navy single-breasted version offers optimal versatility.

Finally, some quality leather boots (whether a chukka, brogue or Derby silhouette), complete with a practical rubber grip sole, in a timeless neutral shade will team perfectly with the rest of your holiday luggage and won’t suffer if you’re trudging through a little snow.

Example Looks

A Winter City Break In Prague, Czech Republic - Men's Outfit Inspiration Lookbook

club monaco winter 2014club monaco winter 2014zara man aw12massimo dutti aw13zara man aw12mango man winter 2014massimo dutti november 2014J Crew Winter 2014House Of Fraser AW137 for all mankind aw14massimo dutti nyc 5th avenue aw14Club Monaco aw14
Key Pieces
  • Asos Wool OvercoatAsos Wool Overcoat
  • Ben Sherman OvercoatBen Sherman Overcoat
  • River Island Knitted Roll Neck JumperRiver Island Knitted Roll Neck Jumper
  • Asos Thermal Lightweight MeggingsAsos Thermal Lightweight Meggings
  • Allsaints Arle Crew JumperAllsaints Arle Crew Jumper
  • Allsaints Wilde SweatpantAllsaints Wilde Sweatpant
  • Berluti Cable-knit Melange-cotton SweaterBerluti Cable-knit Melange-cotton Sweater
  • J.crew Slim-fit Wool And Cashmere-blend OvercoatJ.crew Slim-fit Wool And Cashmere-blend Overcoat
  • Nn.07 Peter Slim-fit Washed-denim JeansNn.07 Peter Slim-fit Washed-denim Jeans
  • Reiss Chiswick Chunky Weave Jumper Bright BlueReiss Chiswick Chunky Weave Jumper Bright Blue
  • Kg Kurt Geiger Godfrey Leather Desert BootsKg Kurt Geiger Godfrey Leather Desert Boots
  • Cheaney Pennine Pebble-grain Leather BootsCheaney Pennine Pebble-grain Leather Boots
Oslo, Norway

Oslo, Norway

Norway’s capital is another idyllic choice for a winter getaway, with its thick covering of snow and the breathtaking Northern Lights that sparkle in the city’s icy waters. Considering temperatures often drop well below zero, you’ll want to make sure you’re equipped to combat the cold.

Start out with a few base layers, whether you opt for technical thermal designs or simply some cotton long-sleeved T-shirts. Much like Prague, you’ll need to pack some solid knitwear options to layer on top – a chunky roll neck jumper or shawl neck cardigan are both good choices for warding off the chill, with both offering additional warmth around your neck.

When it comes to legwear, either do double duty with sturdy slim jeans layered over long johns (or compression tights for fitness fanatics) or, if you’re looking for something more sartorial that still offers all-important insulation, consider a pair of heavyweight trousers in a seasonally-appropriate fabric such as wool, cord or flannel.

Round out your look with some heavy duty outerwear that is able to cope with Oslo’s often harsh elements. A parka in black, grey, navy or traditional olive drab is both snug and on-trend, while down-filled jackets and gilets will help retain your body heat and ensure you stay well insulated.

Look for fur/faux fur hoods where possible – outerwear specialists like Canada Goose use coyote fur around the hoods of its jackets because it never freezes, doesn’t hold water and the uneven hair lengths create a windbreak that protects exposed skin, helping to reduce heat loss from the face.

Finally, pack a beanie or two for additional warmth, along with classic cold-weather accessories such as knitted gloves, a generously sized scarf and pair of robust boots (whether a work or hiking silhouette) that will offer further protection from the biting chill while giving you the opportunity to personalise your look.

Lookbook Inspiration

A Winter City Break In Oslo, Norway - Men's Cold-Weather & Sub Zero Temperatures Outfit Inspiration Lookbook

Simons AW14reserved aw13burton aw13massimo dutti apres ski aw14Hugo Boss Sportswear AW14Simons AW14massimo dutti apres ski aw14penfield aw13peuterey aw13espionage aw14louis vuitton pre aw13Woolrich AW14
Key Pieces
  • The North Face La Paz Down JacketThe North Face La Paz Down Jacket
  • Reiss Butler Shawl Collar CardiganReiss Butler Shawl Collar Cardigan
  • Penfield Hoosac Down ParkaPenfield Hoosac Down Parka
  • Gant Rugger Mens Roll-up Ribbed Beanie – RedGant Rugger Mens Roll-up Ribbed Beanie - Red
  • He By Mango Wool-blend GlovesHe By Mango Wool-blend Gloves
  • Di1309rv03Di1309rv03
  • Richard James Ribbed-knit Wool Rollneck SweaterRichard James Ribbed-knit Wool Rollneck Sweater
  • Sunspel Long-sleeved Thermal T-shirtSunspel Long-sleeved Thermal T-shirt
  • Sunspel Thermal Long JohnsSunspel Thermal Long Johns
  • Linea Vinci Formal Birdseye TrousersLinea Vinci Formal Birdseye Trousers
  • Incotex Slim-fit Garment-dyed Corduroy TrousersIncotex Slim-fit Garment-dyed Corduroy Trousers
  • Uniqlo Men Ultra Light Down Compact VestUniqlo Men Ultra Light Down Compact Vest
Sydney, Australia

Sydney, Australia

Just because many of us are shivering our way through the colder months right now, it doesn’t mean others aren’t basking in the summer sun. Australia’s much-loved coastal city Sydney is currently awash with sunshine, making it the perfect place to properly escape the winter if you’re prepared to go further afield.

With temperatures getting up to 30 degrees Celsius during this time of year, you’ll want to ensure you’ve packed all your lightweight essentials for the trip. But we’re getting ahead of ourselves – your initial priority is dressing for the long haul flight.

Fashion’s current fondness for luxurious takes on leisurewear offers plenty of options for enduring several hours in the air. Try a pair of tailored joggers or broken-in straight-leg jeans with a crew neck T-shirt and cotton/cashmere-blend hoodie or classic sweatshirt to stay warm, stylish and comfortable.

Once you’ve touched down, it’s time to crack out the summer staples, from floral print shirts to pastel legwear. Try a printed T-shirt, short-sleeved shirt or vest with a pair of plain or coloured shorts cut just above the knee when you’re out to catch some rays at Bondi Beach, switching for something seasonally-appropriate but still unquestionably smart when heading for dinner on Darling Harbour – a linen/cotton shirt, unstructured, lightweight blazer and pair of slim-fitting chinos in a summer hue (try white) should do the trick.

Finish off a daytime beach look with breathable leather sandals or espadrilles, and polish off your evening attire with a pair of nautical boat shoes or a smart tasselled loafer.

Last but not least, make sure to pack a light-coloured cashmere sweater for your return. This will not only keep you warm as you step off the plane, but – more importantly – it’ll also make your tan pop and your mates/family jealous.

Lookbook Inspiration

A Summer City Break In Sydney, Australia - Men's Warm-Weather Outfit Inspiration Lookbook

SCOTCH & SODA SS15j crew ss14H&M SS14matalan ss15river island high summer 2015newlook SS15jigsaw ss14Sisley Summer 2014bellfield ss15h&m summer 2012mango man ss14reiss ss15
Key Pieces
  • He By Mango Slim-fit 5 Pocket Cotton TrousersHe By Mango Slim-fit 5 Pocket Cotton Trousers
  • Asos Slim ChinosAsos Slim Chinos
  • He By Mango Leaf Print T-shirtHe By Mango Leaf Print T-shirt
  • Allsaints Tonic Crew TshirtAllsaints Tonic Crew Tshirt
  • Asos Vest With Relaxed Skater FitAsos Vest With Relaxed Skater Fit
  • Uniqlo Men Premium Linen Long Sleeve ShirtUniqlo Men Premium Linen Long Sleeve Shirt
  • Hentsch Man Printed Cotton-poplin Short-sleeved ShirtHentsch Man Printed Cotton-poplin Short-sleeved Shirt
  • Polo Ralph Lauren Woven-cotton ShortsPolo Ralph Lauren Woven-cotton Shorts
  • Rivieras Cotton Mesh Slip-on ShoesRivieras Cotton Mesh Slip-on Shoes
  • J. Crew 9 Stanton ShortJ. Crew 9 Stanton Short
  • Blue Harbour Pure Linen Easy To Iron ShirtBlue Harbour Pure Linen Easy To Iron Shirt
  • Austin Reed Contemporary Fit Sand Linen JacketAustin Reed Contemporary Fit Sand Linen Jacket
  • J. Crew 10.5 Stanton ShortJ. Crew 10.5 Stanton Short
  • He By Mango Leather Boat ShoesHe By Mango Leather Boat Shoes
  • Kurt Geiger Keldy Leather SandalsKurt Geiger Keldy Leather Sandals
Copenhagen, Denmark

Copenhagen, Denmark

One of Europe’s most stylish destinations, Copenhagen is a hub of colourful old buildings and distinctively Scandinavian design. It’s also pretty cold in winter, too.

You can expect temperatures between 5 and -2 degrees, so you’re best opting for a combination of the cold-weather essentials we’ve previously outlined for Prague and Oslo (heavy duty knitwear, outerwear, knitted accessories and possibly thermals) but remembering to put a more sleek, minimalist bent on it all.

Renowned for their often sparse approach to aesthetics, the Scandinavians are unrivalled in their ability to do pared-back so, when in Rome…

Keep to a palette of white, grey, black and navy, and opt for sportier technical fabrics such as cotton, neoprene and nylon. For daytime, try some slim jeans and a sports luxe sweatshirt over a button-down Oxford shirt, with a heavyweight bomber jacket on top to complete the look.

For something more evening-appropriate, swap the jeans for a pair of wool trousers and the jacket for a sleek black overcoat.

Footwear is key in Copenhagen as you’re bound to do a lot of walking or cycling as you explore the city’s streets. You can’t go wrong with a pair of minimal leather trainers in a neutral colour, which can adapt to both smart and casual occasions.

Lookbook Inspiration

A Winter City Break In Copenhagen, Denmark - Men's Minimal Cold-Weather Outfit Inspiration Lookbook

Reiss AW14The Kooples AW12Ami AW13Day Birger Et Mikkelsen AW11H&M AW14Selected Homme Jeans AW14River Island Holloway Road AW14Cos AW14Bally AW14Urban Outfitters AW12Burton SS15Boglioli AW12
Key Pieces
  • Topman Rains Blue Long Waterproof JacketTopman Rains Blue Long Waterproof Jacket
  • Rains Short JacketRains Short Jacket
  • River Island Long Sleeve Oxford ShirtRiver Island Long Sleeve Oxford Shirt
  • Allsaints Tawn Crew JumperAllsaints Tawn Crew Jumper
  • Allsaints Utility Leather JacketAllsaints Utility Leather Jacket
  • Nicce Wool Bomber JacketNicce Wool Bomber Jacket
  • River Island Light Grey Cotton Ribbed Crew Neck JumperRiver Island Light Grey Cotton Ribbed Crew Neck Jumper
  • Orlebar Brown Dudley Loopback Cotton-jersey SweatshirtOrlebar Brown Dudley Loopback Cotton-jersey Sweatshirt
  • A.p.c. Petit Standard Slim-fit Dry Selvedge Denim JeansA.p.c. Petit Standard Slim-fit Dry Selvedge Denim Jeans
  • Reiss Max Patch Pocket T-shirt GreyReiss Max Patch Pocket T-shirt Grey
  • Common Projects Original Achilles Leather SneakersCommon Projects Original Achilles Leather Sneakers
  • Want Les Essentiels De La Vie Lennon Leather And Mesh SneakersWant Les Essentiels De La Vie Lennon Leather And Mesh Sneakers
London, UK

London, UK

Last but by no means least, the UK’s ‘Big Smoke’ is worth bearing in mind if culture and shopping take precedence over fair weather on your winter getaway priorities list.

The weather in London is changeable to say the least; what’s pretty much guaranteed though is that you’ll encounter wind and rain during the colder months, so it’s worth investing in a high quality umbrella that is strong enough to withstand strong gales and even hail. Brands such as Fulton and London Undercover (how apt) offer superb designs that deliver fashion and function in equal measure.

For the rest of your look, you’ll need to pay attention to the forecast before flying. If temperatures are nearing zero, an overcoat or parka is advisable, but if all you’re likely to encounter is a brisk breeze, you’ll get away with a waterproof trench or mac – a lightweight style crafted from cotton or nylon is ideal for layering knitwear underneath.

Smart-casual is the name of the game here, so consider packing a selection of slim-cut wool trousers and cotton chinos, along with a few button-down shirts, casual lightweight jumpers and thin gauge roll necks to create a versatile capsule travel wardrobe that can adapt to any occasion.

When it comes to footwear, try a clean and crisp pair of trainers or a classic desert boot in leather, as you’ll likely be doing your fair share of walking through the capital, despite its award-winning public transport infrastructure.

Come evening, don a well-cut suit in a winter-appropriate fabric such as wool or flannel to catch a show in London’s renowned West End. Whether you opt for a single-breasted two-piece, or pull out all the stops with a three-piece, combine with a crisp white shirt and leather brogues to complete the outfit.

For those of you who want to explore the city’s varied nightlife, this suit can also be split into separates to produce a variety of sharp, smart-casual looks that would see you breeze entry into many of the capital’s high-end establishments, from bars and clubs to restaurants. Try teaming the blazer with your slim chinos or wool trousers, and the trousers with your roll neck and mac.

Lookbook Inspiration

A Winter City Break In London, UK - Men's Smart-Casual Cold-Weather Outfit Inspiration Lookbook

Jigsaw AW13Debenhams SS14H&M AW14Farah SS14Burton AW14He By Mango AW13Suitsupply AW14De Fursac AW13He By Mango AW13He By Mango AW12Avva AW14Boglioli AW12
Key Pieces
  • He By Mango Slim-fit Herringbone Wool-blend ChinosHe By Mango Slim-fit Herringbone Wool-blend Chinos
  • Asos Merino Roll Neck JumperAsos Merino Roll Neck Jumper
  • Sisley Formal Shirt In Slim FitSisley Formal Shirt In Slim Fit
  • Reiss Riddle Merino Crew-neck JumperReiss Riddle Merino Crew-neck Jumper
  • Reiss Earlsworth Lightweight Mac Bright BlueReiss Earlsworth Lightweight Mac Bright Blue
  • Reiss Muller B Fleck Weave BlazerReiss Muller B Fleck Weave Blazer
  • Sandro Double-breasted Cotton Trench CoatSandro Double-breasted Cotton Trench Coat
  • London Undercover City Gent Multi-braid Malacca Wood-handle UmbrellaLondon Undercover City Gent Multi-braid Malacca Wood-handle Umbrella
  • Club Monaco Grey Grant Slim-fit Wool-flannel SuitClub Monaco Grey Grant Slim-fit Wool-flannel Suit
  • Churchs Enmore Leather BroguesChurchs Enmore Leather Brogues
  • T.m.lewin Charcoal Wool Flannel Slim TieT.m.lewin Charcoal Wool Flannel Slim Tie
  • Asos Chukka Boots In LeatherAsos Chukka Boots In Leather
Final Word

Wherever you choose to go this winter, make sure to research the destination’s climate beforehand and check the weather forecast right before you fly. Take note of the average temperatures so you know how much knitwear you should pack, or the rainfall to decide whether you’ll need waterproof outerwear.

Now you’ve heard it from us, we’d love to hear from you. Are you planning on booking a last minute winter getaway, or have you already booked one? If so, what style essentials will you be packing for your trip? Are there any other city break destinations you would like style advice for?

Let us know in the comments section below…