What To Pack for a Winter City Break

 There’s just something so appealing about a winter city break, exploring a new city when the stores are brimming with Christmas decorations and the streets are twinkling with pretty lights. What can be difficult however is knowing what to wear for this type of holiday. To me, the aim of winter city break outfits is always to look as stylish as possible whilst keeping me warm and my feet comfortable given you are most likely going to be outside and on your feet for the majority of each day. And yet this can feel near impossible when you need to travel light for your short trip all thanks to luggage restrictions.

But where there is a will, there is a way! As a seasoned pro when it comes to packing small carry-on cases for all kinds of holidays, I’ve put together this guide to provide you with inspiration of what to pack as well as some carefully thought-out winter city break outfit ideas for your next cold season getaway.

Packing Essentials To Create the Perfect Winter City Break Outfits

You’ve booked your trip whether it be to Prague, Iceland, Krakow, or anywhere in between, and now it’s time to pack. But then the fear sets in…what on earth do I take?! It’s going to be at least -1 degrees so you’ll need a coat, but your warmest will surely take up too much room? And what about footwear? You’re going to need something waterproof yet comfy. And on top of all this, how are you going to keep warm and comfortable yet look cute? It’s an age-old conundrum that has people dreading packing for a winter city break.

But it doesn’t have to be that way. There are some absolute winter city break outfit essentials that you can pack with confidence knowing you’ll be cosy, comfy, and cute on your trip.

Comfy Footwear

Chunky Boots

Oversized Alpaca Wool Jumper, Leopard Print Midi Skirt, Heeled Fur Lined Biker Boots

For days spent exploring your city of choice in the winter, comfort is key, particularly when it comes to your feet. Mine are the absolute worst for blistering so a comfy pair of boots is an absolute winter city break outfit essential for me (as well as a pack of blister plasters, just in case!). Whether it’s a pair of Ultra Mini Uggs or your trusty Chelsea boots, you need to make sure it’s something that will keep your feet feeling comfy the whole day.

If you’re going somewhere where rain is looking likely, consider your footwear carefully. Whilst you may be desperate to take your brand new Ugg Tasmans for a spin, think whether you want to take the risk of muddy rainwater splashes. If you do plan on taking any suede boots or shoes, I would highly recommend protecting them with a Shoe Protector Kit prior to travelling to avoid any water damage.

Shoes can take up a lot of space in your luggage, so if you’re packing light for your winter city break, my best recommendation to maximise the number of shoes you can take would be to wear the chunkiest pair you’re taking on the plane as you travel. Yes, it may be annoying having to take off your buckled biker boots at security, but you’ll sure save on room in your carry-on!

Similarly, opt for a pair of boots that can double up as cosy evening footwear too. This means choosing smart footwear that looks equally as good with your daytime looks as it will your evening fits. If your feet can manage it during the day, go for a chunky heeled boot…and if they can’t, make sure you pack those blister plasters! I’ve linked some gorgeous pairs perfect for day-to-night styling below.

Low Heels

If you’re not short on space because you’ve forked out for hold luggage, then definitely pack a pair of heels for your evening looks! If you plan to walk everywhere to soak up the sights by night, you’ll want to keep them low or at least opt for a block heel. Many European cities are paved with pretty yet painful cobbled streets so think carefully about your heel choice. I’ve linked some ideal options below.

A Warm Coat

The Camel Coat

Camel coat, Baker boy hat, winter city break outfit

Next up on your packing checklist for your winter city break outfits? Definitely a warm coat. Winter city breaks can be bitterly cold depending on how far into winter you’re planning to visit your city of choice. For a lightweight yet super cosy option, I would recommend packing a longline coat. Something like my trusty & Other Stories camel coat is ideal as it’s surprisingly light so it folds well in a small suitcase yet its fantastic quality means it will keep you snug all day long. Its lightweight feel means it’s also a great option for layering over chunky jumpers so you don’t feel strangled and bulked out.

The Trench Coat

Trench Coat, Jeans, Ultra Mini Uggs

Another light-duty option is the trench coat. Although they don’t seem the warmest of options, just like our friend the camel coat, trench coats are fantastic for layering. They are also a great choice if the weather forecast is looking wet and windy as many high-street styles are water-repellent.

The Puffer Coat

Puffer Jacket, Brown Leather Trousers, New Balance Trainers

If you’re looking to go hard with your winter coat for your trip, consider a puffer coat. Not only are they a great option if it rains, but they are also super insulated and will keep you toasty warm whilst looking it-girl-approved. A puffer coat, or ski coat, is a winter city break outfit essential if you’re heading for the slopes or to somewhere super snowy and cold like Iceland.

The Fur Coat

MANGO Faux Fur Shearling Coat

Finally, if you’re jetting off somewhere you know will be staying dry during your stay, or you’re willing to carry an umbrella all day, you could always go full winter chic with a fur or teddy coat. Styled with a cute pair of furry earmuffs or fur hat/headband, you’ve got the ultimate Christmas market-worthy look.

Cosy Knitwear

Black High-Neck Jumper, Ecru Jeans, Baker Boy Hat

This one is a given. If you’re heading for a winter city break, you’re going to need some cosy knitwear. Think chunky jumpers, fine-knit jumper dresses that will take you from day to night, and oversized cardigans or sweaters. If you’ve opted for a lightweight coat option, go as chunky as you like with your knitwear underneath. But what about when you head into a cafe or restaurant and the heating is on full blast, I hear you say. This is where our next winter city break essential to pack comes in…base layers.

Base Layers

Base layers are a must-have component to all of your winter city break outfits. Going from freezing cold temperatures outside to melting hot temperatures inside can cause havoc for your outfit choices. This is where base layers are fantastic. Whether it’s a seamless bodysuit underneath your chunky jumper or a fine-knit turtleneck underneath a heavy-duty cardigan, base layers act as an extra layer of warmth in the cold but a saviour piece in the warmth when you’re sweltering in a coffee shop and need to throw off your jumper and scarf.

Consider investing in some thermal leggings if you’re going somewhere super cold. You can wear these under ski pants or trousers for extra warmth. Or, if you’re just wanting some stylish leggings for your winter city break outfits that are of a thicker quality than your standard pairs, thermal leggings are a fantastic option.

A Hat, Scarf, & Gloves

The ultimate accessories for your winter city break outfits, don’t forget to pack a hat, a scarf, and a pair of gloves.

The Beanie Hat

 In terms of hats, the possibilities are endless so it really depends on your vibe. For a Scandi-inspired look, opt for the fail-safe beanie hat, adding casual cool vibes to any fit.

The Wool Floppy Hat

Checked Coat, Thigh-High Boots, Wool Floppy Hat

For something that bit more chic, consider a wide-brim wool floppy hat. These look great styled with a jumper dress, thigh-high boots, and fur coat for a glam yet cosy evening look.

The Borg Bucket Hat

Borg bucket hat and fur aviator jacket

Looking for something a bit fun to spice up your winter city break outfits? I love a borg bucket hat styled with a fur aviator jacket.

The Checked Wool Scarf

Checked Scarf, Aviator Jacket, Ultra Mini Uggs

Scarves have had a bit of a moment in recent years and it seems the more colourful, the better (thank you Acne Studios for starting this fabulous trend). Add a pop of colour to neutral outfits with a woolly checked scarf in hues pink, blue, or green.

The Gloves

When it comes to gloves, they can be super annoying to take on and off but they really do add an extra something to an outfit (and of course keep your hands warm). Leather gloves, especially those with fur trims, are my absolute favourite and can really take a simple winter look to a whole other level. But if you’re planning on taking an insane amount of photos on your winter city break, a pair of touchscreen-friendly gloves are the perfect solution for you so you don’t have to keep taking them on and off!

Crossbody Bag

Coach Tabby Bag

For a winter city break, or any city break for that matter, I would always recommend taking a crossbody bag. Not only do they look great, but they’re perfect for keeping your valuables (including the bag) close to you in busy city settings, keeping your hands free and saving your arms from carrying a heavy handbag all day long.

Winter City Break Outfits

It may seem like a daunting task to put together your winter city break outfits, but I hope this guide gives you the confidence you need to pack the essentials which will have you looking stylish yet keep you cosy and comfy.

Take a look at my other guides for more packing inspiration

What to Pack for a Summer Holiday in the Autumn 

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Julia Catherine Ward
Julia Catherine Ward

Julia has been posting style, beauty, and travel related blogs since 2012 (long live Tumblr!). Enjoy the post and please leave your comments!

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