Jet-Setting Style: What To Wear On A City Break

CHO Fashion & Lifestyle
Young man and woman wear beige overcoats over black sweatshirts

Long winters call for impromptu trips abroad, and what better way to overcome the winter blues than with a city break somewhere new?

Although choosing where to go for your trip may be easy, packing the perfect city break outfits can prove challenging, particularly if your destination has a changeable climate. From choosing coats to footwear, sometimes the hardest part is navigating how to fit everything you need into your carry-on luggage.

If you're running short on city break outfit ideas, don't worry; you'll find everything you need at CHO. In this guide, we've pulled together a variety of outfits for city breaks for both men and women, so you don't have to. Read on for our top styling tips and our ultimate city break packing list, and avoid ending up somewhere new without all of your essentials!

Young man and woman wear beige overcoats over black sweatshirts

Table of contents:

What to wear on a city break

Women’s city break outfits

Men’s city break outfits

Our ultimate city break packing list

What to wear on a city break

Short breaks can be the hardest to pack for, particularly if you're trying to pack your whole wardrobe into your carry-on. Here are some handy ways to plan your outfits to avoid over or under-packing:

Master the art of the capsule wardrobe

The best way to master dressing for a two to three-day city break is to perfect the art of creating a capsule wardrobe tailored to the climate of your destination. The ideal approach is to choose interchangeable outfits to subtly adjust your outfit throughout the trip to incorporate new accessories or garments tailored to the situation.

For example, if you opt for a cute t-shirt and jeans for a day filled with sightseeing, you could simply swap out the jeans and wear a skirt for your evening meal to elevate your look and make it more appropriate for the situation.

Similarly, for men, if chinos and trainers are your daytime city break style, paired with a crisp, new t-shirt, swap it out for a shirt in the evening to take your style to the next level.

A lightweight capsule wardrobe filled with interchangeable pieces can make for a more practical approach to packing, as you're only packing exactly what you need, leaving room for any spontaneous purchases you might make along the way.

Stylish and practical footwear

When choosing footwear, always opt for something comfortable, particularly if your trip involves a lot of walking. While it may look chic to be strutting the streets of New York or Paris in those designer heels or a new pair of penny loafers, your feet won't be very thankful for it as the day wears on.

Get the most out of your trip by packing your favourite pair of comfortable trainers, guaranteeing fuss-free feet, step after step! Choose a pair that looks just as good dressed up as they do dressed down, so you can mix and match them with your casual and more formal outfits.

If trainers aren't your thing, a comfortable pair of shoes or boots can add just as much flair to your outfit without compromising comfort.

Top considerations when planning and packing city break outfits

Young woman wears a cap and overcoat with a sweatshirt

Footwear and strategic folding aside, here are some of our top considerations when planning city break outfits to help you ace your packing:

  1. Consider the time of year you're travelling and the climate of your destination. If you're travelling from the UK in winter, opt for layers that are easy to remove if you're heading to a hot destination. Clever layering is the best way to cope with any climate change. Wear your bulkiest clothing to save all important room in that carry-on.
  2. Hotter climates require lightweight fabrics such as cotton and linens, so pack accordingly. Similarly, consider thicker cotton, wool and cashmere layers if you head somewhere cold.
  3. Remember that there may be a temperature difference when outdoors compared to inside. For example, hotter climates may have cold, air-conditioned shopping malls, so you may need an extra layer indoors, whereas buildings in colder climates may have the heating turned up to a cosy level, so be sure to dress with that in mind.
  4. If you're doing activities that require a specific outfit, such as a bikini or swim shorts for the hotel spa or a formal outfit for the opera, make sure to pack those.
  5. Choose a simple, neutral colour scheme with a couple of statement garments so that all your clothing choices will coordinate, mix and match.

Women’s city break outfits

So, now that you have some basic ideas on coordinating your capsule wardrobe, we thought we'd offer some style inspiration to get you started. With a focus on clever layering, here are some of our top women's city break outfit ideas to give you a desirable, chic, fuss-free city break look!

Women’s city break inspiration for a cold climate

Young man and woman wear overcoats with sweatshirts, jeans and trainers. They pose together

If you're heading to a city with a climate similar to the UK or colder, layering will be your best friend. Choose an oversized coat, like the Tommy Hilfiger Wool Blend Women's Long Classic Jacket (pictured above), to layer over a cool sweatshirt for days spent sightseeing or hitting the shops.

Jeans and trainers are a great fit for this look, adding style and comfort. Tommy Hilfiger Elevated Feminine White Trainers are a great choice for completing the look for fashion meets function dressing.

Woman poses in a red and black Ted Baker dress

Ted Baker Breetah Women’s Angel Sleeve Mini Dress

When the evening comes around, switch out your sweatshirt and jeans for a chic dress such as the Ted Baker Breetah Women's Angel Sleeve Mini Dress. Complete the look with stylish mid boots and prepare to put your best foot forward!

Women’s city break inspiration for a warm climate

Layering can work effectively if you're heading somewhere hot to escape the winter chill. Start with a cool base layer that will be perfect for sunny climes, such as the Barbour Rutherglen Women's Midi Dress and layer over a stylish sweatshirt of your choice to keep you warm and cosy whilst travelling on the plane.

women wears Barbour summer dress and pairs with bag and sandals

Barbour Rutherglen Women's Midi Dress

On arrival, swap out your trainers for sandals and sunglasses and get ready to enjoy the sun (just don't forget to pack that all-important sunscreen in your carry-on!). Fill your carry-on with lightweight t-shirts and shorts that pair perfectly with your sandals for several summer-inspired looks.

Men’s city break outfits

The perfect men's city break look can be easily achieved if you layer your look strategically. Whatever the climate, you can achieve a lot with a smart-casual pair of trousers that can be dressed up or down and a selection of sophisticated polo shirts. Here are our top tips to help you achieve the most from your carry-on capsule wardrobe.

Men’s city break looks for cold climates

Close up of a man wearing an overcoat with a hoody and a Fred Perry hat

When jet-setting to cool climes, layering is key, and you can almost get away with wearing a complete outfit that you can de-layer as the trip progresses.

Start by choosing some stylish chinos and a classic polo shirt, such as a Fred Perry Men's Plain Signature polo shirt, which would serve as the perfect, classic look for a stop-off in a stylish restaurant on the evening of the first day of your trip. Layer over a pullover hoodie and complete the look with a cosy yet smart coat such as a GANT Mens Classic Tailored Fit Wool Topcoat (pictured above). For evening dressing, simply remove the hoodie and pair your coat with chinos and a polo for a sophisticated look. Trainers or shoes will work well with this look, but if you can only pack one pair, always choose your most comfortable style.

Looking for extra layering? Opt for a designer wool hat or cap to complete your look and beat the winter chill!

Men’s city break looks for warm climates

Packing your carry-on for a sunny location is generally easier, as lighter layers take up less space. As a rule, packing two pairs of shorts, one for casual settings, such as swimming shorts and a more formal pair, such as chino shorts, should carry you through your trip.

For evening wear, choose a lightweight pair of chino trousers that can be worn in casual and formal settings to save space on doubling up. Two shirts, two polo shirts and a more formal shirt should cover the basics for a sun-filled city break.

If you've got room for multiple pairs of shoes, pack trainers that are great for walking yet smart enough for a relaxed evening meal, then opt for sandals for relaxed days by the pool.

GANT duffle bag

For this sort of city break, a good duffle bag should be sufficient to house everything you need for travel. Then, when unpacked, you can use it to carry your essentials to the pool or beach!

Our ultimate city break packing list

So now you know which clothes to pack, what about everything else?

Don't worry, we've thought about that too! Here's our round-up of all the rest so you can easily plan for your city break without worrying about turning up at the airport without all the essentials!

  1. Tickets, documents and money

Don't forget your passport, as you won't get far without it! Whether you're carrying all of your important documents on your phone or in your travel wallet, give everything the once over before you leave (and make sure you pack a charger so you don't have any technological mishaps!).

Take extra ID and a backup bank card as a precaution, just for extra reassurance, should anything go wrong.

  1. Toiletries & cosmetics

One that's unique to you; you'll need to pack what you use every day, alongside important things like sunscreen. The key here is not to forget important things like feminine hygiene products, contact lenses and anything else you can't live without. Oh, and don't forget your toothbrush!

  1. Travel essentials

Whether it's a sleep mask and a refillable water bottle, or a lightweight blanket, fluffy socks and a good book, travel essentials can help you survive a flight, coach trip or train journey. Pack them so they're easy to access.

  1. Tech essentials

It could be something as simple as a phone charger or a backup battery pack, but if you think you can't live without it, it might be worth packing. A phone charger or a charger for your earphones could be essential for a long flight or accessing those all-important documents on your phone for your return trip, so make room for them.

  1. Essential first aid kit

One that can easily be altered depending on your travel destination, but remember to pack any essential medication, pain remedies, mosquito repellent or allergy pills. Blister plasters are also a great addition, particularly if you plan to spend hours on your feet.

Find your perfect city break outfit at CHO

Whatever your style preference, you can find your perfect city break outfits at CHO by browsing the links above. Then, for all your other essentials, browse our handy packing checklist to find everything you need. Looking for the perfect holdall to house everything? Why not browse our men's and women's bags to complete your city break kit?

Related posts:

What Are The Best Men’s Winter Jackets?

Men’s Fashionable Winter Layering Tips

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

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