Winter Breaks: Dressing for the City


While there’s nothing better than booking a summer holiday for a slice of sunshine, winter breaks can be just as appealing. Rain, hail or shine, the beauty of the city remains. Despite the cold, you can still enjoy everything your chosen destination has to offer. Whether it’s visiting the Louvre in Paris or strolling through a frosty Central Park in New York, there are so many wonderful things to bring you joy this time of year.

After refining the details like flights and accommodation, you can turn your attention to thinking about what to pack. Packing can be problematic if you find the process overwhelming. Even a two-night getaway can pose a number of fashion dilemmas.

To help you along, we’ve put together a selection of outfits to inspire your packing for a winter escape. From airport attire to dinner dates, we’ve attempted to cover all city break scenarios to ensure you remain stylish the entire trip.

The Journey

The trip to your destination is the very beginning of your getaway, so it’s nice to get going in style. Whether you want to take an obligatory airport selfie or try out your new tracksuit, you can have as much fun with planning your travel attire as you can your evening wear. But whatever you decide to wear, comfort should reign over all else.

Whether you’re taking the car, the train or a plane, transportation typically involves a lot of sitting. Therefore, anything loose-fitting is a good idea. Tight clothes, such as jeans, will likely cause discomfort as you remain in one place for a matter of hours. You want to be able to move your body around (within reason) while you’re on the move, especially for longer journeys.

Given that there might be a lot of walking in between, your footwear should also be a comfortable choice. Avoid heels and opt for an easy flat, like a pair of trainers or slip-ons. We recommend something that offers comfort head-to-toe, like this pair of roomy joggers, a cosy knit for keeping warm along the way and the Holland Cooper backless Kingston loafers. Don’t forget an eye mask for plane naps.

Jules B Outfit Inspiration

Breakfast and Brunch Dates

If you’re only away for the weekend, every occasion, no matter how small, calls for outfit planning. You might prefer to roll out of bed and go for a quick continental breakfast locally, but if you want to really make the most of your wardrobe, you can style yourself accordingly. We suggest opting for effortless elegance, a casual look made of staple basics coupled with the odd wow piece. Take the outfit below, which brings together FRAME’s Le Slim Palazzo jeans, a classic white shirt (with an enlarged collar) and chunky Chelsea boots. These are simple pieces that work in any setting, but to make it punchy, we’ve added Essentiel Antwerp’s heavyweight checked cardigan in red and pink.

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Sightseeing and Exploration

Exploring a city in the winter time can be a magical experience. But as the elements make sightseeing a little more tricky, it’s necessary to dress appropriately in case of rain, snow or freezing cold. Of course it depends on the location, but lots of walking can quickly raise your temperature. So in this case, the trick is to be wrapped up, but not too much. Certain cities call for thorough insulation when outdoors, but in milder temperatures, a hoodie and coat can suffice. Layering is always a good solution, as you can remove a layer or two if you overheat when attending museums, art exhibitions and other indoor activities.

Accessories-wise, sunglasses are a must. You don’t want to traipse about town with the sun in your eyes, potentially missing out on your surroundings. Your choice of bag is also important. Carrying something bulky around all day can spoil your adventures. To maintain movement of your arms and prevent back or shoulder strain, a cross-body bag is perfect. You’ll remain hands-free for snapping memories, carrying a cup of coffee and simply enjoying the freedom of having your arms free.

Like your travel outfit, sensible footwear is non-negotiable for exploring. Trainers are ideal, but weather-dependent, you might prefer a waterproof boot in the cold season.

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Late Night Dinners

Dinner is the most perfect time to dress up on holiday. If you’ve spent the day in your comfortable fits, makeup free with unstyled hair, it’s always nice to dress up after sundown and venture out to wine and dine. Your personal style comes into play here, as you still want to feel comfortable as you indulge in the local cuisine. But whether you decide to dress to the nines (after all, you’re on holiday) or prefer something a little pared back, your dinner fit should be equally as elegant.

You may not be in a hot climate, but that doesn’t mean you can’t wear a gorgeous dress. It just needs a few tweaks to match the season. Here, we’ve styled the Dea Kudibal Olga dress with the Alias Mae leg-hugging suede boots and a wear-with-everything jacket from Joseph. Introduce sparkling jewellery and a velvet clutch and you’re ready for whatever the evening unfolds.

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Day-To-Night Drinks

We’ve covered the dinner outfit, but what about drinks? This is another opportunity to glam up, and it’s always a bonus if your outfit is wearable from day to night. That way if you end up out longer than expected, there’s no need to rush home to change. A trouser suit can work well on these occasions. It will keep you covered and warm enough in between bars, it works with heels and flats alike, and it’s easy to dress up with accessories. As you can see below, Joseph’s Ottoman jersey blazer and trousers work effortlessly with a pair of black pointed heels.

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Evening Strolls Under City Lights

Depending on where in the world you are, leaving the hotel for a walk on a cold night can be a perfect end to the day. Whether you’ve felt cooked up inside all day or you like a dose of fresh air before bed, seeing the city at night can be a lovely and different experience to the daytime, especially with those dazzling city lights. Despite the warming glow of street lamps, this is the time to wrap up. We recommend cosy pieces, like the Eddy & Ivy cashmere 1985 jumper with a pair of wide-leg trousers and a voluminous puffer coat.

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Hotel Lounging

After a long day of exploring and ticking off everything on your city’s bucket list, it’s back to the hotel to unwind. For many, the hotel stay is as joyous as seeing the city itself. Even a couple of days just being away from home and settling into a new environment, away from work and household chores, can reset the mind. As well as enjoying a luxury bed, it’s nice to pack a pair of pyjamas to make the most of your lounging experience. After a hot soak, slip into a pair of Chelsea Peers pyjamas under your hotel dressing gown, find home comfort in your slippers, and don’t forget an eye mask if you can squeeze in a lie-in before the sun rises.

Jules B Outfit Inspiration

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