City Break Outfits: 4 Top Picks That Will Fit In Your Hand Luggage | THE STYLE INSIDER
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There’s nothing quite like a city break to refresh your body and mind, getting you away from the mundane to have your own adventure. With a world of opportunities, where you go is up to you; as long as there is sun, sand and plenty of cocktails, it sounds good to us. The only issue with city breaks is, more often than not, you’ll be taking hand luggage over a suitcase. Don’t worry though, we think you need a few key pieces and simply style them in different ways. Need some inspiration? Here are our favourite city break outfits to get you started.


Here are the absolute key pieces we recommend packing in your hand luggage, although we’ll chat about what else you’ll need later on.

  • White trainers – They don’t have to be white per se, but this colour works well with most outfits. Wear a comfy pair to the airport so you don’t have to worry about space.
  • Cuffed shorts – Cuffed shorts are super flattering, especially if they’re in a mom or boyfriend fit.
  • Bodycon dress – Whether it’s for a night out or dinner at the hotel, bodycon dresses are a must when going on holiday.
  • Strappy sandals – bonus points if they have a chunky wedge.
  • Satin shirt – You’d be surprised how versatile a satin shirt can be, making it a vital piece in your hand luggage.
  • Culottes – Comfy, cooling and casual, what could be better?
  • Jeans and tights – We’re presuming the weather is warm in the outfits below, but that may not be the case. Swap the shorts for your favourite fit of jeans and wear tights if you’re going later in the year.



Unless you’ve planned out every aspect of your city break, you’ll need versatile outfits that work for a manner of events. Plain bodycon dresses are amazing for this as they act as a blank canvas for accessories. Choose one that has thin straps for a chic yet summery feel, opting for white or pastel shades such as baby blue or millennial pink.

Another versatile piece is a cream satin shirt. You may think this can only be worn tucked into trousers – which looks fab, by the way – but this is far from the truth. Instead, wear it over the dress, leave the buttons undone and tie it like a crop top under your bust. You can bring the shoulders down slightly in more of a Bardot style if you prefer this look.

Accessories should be subtle and dainty to ensure the look is refined rather than brash. Layered coin necklaces paired with a crossbody bag should do the trick. We recommend the Maddie Stitch Circle Bag from Ted Baker due to its ability to make a contemporary style statement.

When it comes to shoes, choose between trainers or strappy white sandal wedges.

Rob’s top tip: If you don’t feel confident in a bodycon dress, swap it for a skater style.  It flares out at the hips rather than being completely figure hugging and is, therefore, a lot more forgiving.



Remember what we said about satin shirts being versatile? To prove it, we’re using it again in this look. You’ll have limited space in your hand luggage after all, so bringing pieces you can wear in different ways is vital.

This time, you’ll be wearing the shirt in a more traditional way. Button it up as normal, leaving a few undone at the top to show off a flash of skin and highlight your collar bone. Tuck the shirt into some cuffed mom-style denim shorts, making sure to loosen it slightly at the bottom.

For accessories, add a chunky belt buckle. You’d be surprised at how this can pull the entire outfit together. This is a casual look for exploring the city, so don’t go crazy with the statement pieces and opt for some tortoiseshell hoops instead. We’d recommend choosing trainers for this look, especially if you’re planning on walking around the hot spots.

Rob’s top tip: If you’re going somewhere especially hot, remember your sunnies and a hat. This outfit would look amazing with aviator sunglasses and a floppy sun hat as both exude Hollywood glamour.



The next look is another that is simple yet stylish, giving you that effortlessly chic look that everyone desires.

Culottes are breezy and easy to style, making them the perfect choice on a warm day in your chosen city. Avoid black and other dark colours, favouring white, khaki or stone instead to suit the new environment you’re in.  

For tops, you have a couple of choices depending on the style you prefer. White or grey fitted crop tops look stunning when combined with flowy culottes and pieces with frill edging are all the rage this year. If that’s not for you, try a strappy vest bodysuit or cami to get the same effect without revealing your midriff.

Rob’s top tip: Both trainers and sandals look great with culottes, so you may want to consider the activity you’re getting stuck into that day. Trainers are far superior when you’re doing a lot of walking, but a trip to a bar may require heeled sandals in order to formalise the look.



This one is another easy option, but a great choice for heading into the city centre when it’s hot outside while making the most out of your hand luggage.

Whether you decided to bring a bodysuit, cami or crop for outfit number three, you’ll be using it in this look. Pair your chosen top with the mom shorts from outfit one and choose some casual brown sandals.

You can be a bit more extravagant with your choice of jewellery with an outfit like this, but don’t go overboard. If you’re choosing statement earrings, go for a subtle necklace and vice versa.

A waist bum bag is practical and stylish, both of which are necessary when going away.

Rob’s top tip: If there’s a slight chill in the air, an oversized cable knit cardigan will keep you warm and match every outfit flawlessly. Choose one with large tortoiseshell buttons, cuffed sleeves and a crop fit to pull off the trend perfectly.