City Break Outfits

Button through Strappy Maxi in Green Floral
Button through Strappy Maxi in Green Floral

There’s nothing quite like a city break. Exploring historical landmarks, trying local cuisine, and soaking up cultural hot spots. However you like to enjoy a new city, there’s one thing for sure we know you’ll want to tick off your list – taking holiday snaps in your cute city break outfits, of course!

But deciding what to wear for a weekend away can be tricky business. You need to consider the time of year and weather to dress appropriately, and enough suitable clothes for all of your sightseeing activities.

If you need a helping hand, then you’re in the right place. The style gurus at SilkFred have pulled together this handy guide on dressing for a city break. So whether you’re off to bustling Barcelona or the romantic streets of Rome, we’ve got you covered.

We’ve done the planning, so you can get packing…


Our top tips on packing for a city break 

  • Whatever the weather: Unlike a beach holiday, a city break usually means milder temperatures. Make sure to consider what season you’re travelling in and check the weather forecast well in advance, this will help you inform your fit vibe. If in doubt, layering is your best shout. If you’re heading somewhere warm that might get chilly in the evenings, cardigans and denim jackets are perfect for popping in and off.

  • Treat your feet: City breaks are notorious for a lot of walking, so it’s essential that you have the appropriate footwear. Nobody wants to be hobbling around a new city with blisters all over their feet. Make sure to invest in some comfy trainers if you’re planning on getting the steps in.

  • Clever carry-on: It’s likely that you’re only going away for a few nights, which means you might not have much packing space to play with. But this doesn’t mean you need to compromise on style! To save space, pick 1-2 staple items, like a statement maxi skirt or some cute shorts, and fill the rest of the case with basic tops that you can mix and match, creating new outfits each day. Another hack is wearing your heaviest clothes on the plane, like jeans and chunky boots. Look at you, savvy jetsetter!

Travelling light? Check out even more top holiday packing hacks here.

The Classic Day Dress

We love a day dress for a city break. From adorable tea dresses to floaty, elegant maxis, there’s a cut and style to suit everyone – and every city. Plus, they’re easy to dress up or down depending on your activities. Simply throw on some chunky classic trainers and a lightweight jacket, such as a trench or a denim jacket, and you’re ready to see the sights. Heading to dinner? No problem, swap your trainers for some chic ballet flats or heels and a blazer, and you’re ready to eat. Bon Appétit!

Hem Detail Tiered Maxi Dress In Light Blue
Hem Detail Tiered Maxi Dress In Light Blue

The Midi Skirt and Top Combo

Name a better duo than a midi skirt and top combo – we’ll wait. It’s just as easy to throw on as a pair of jeans but gives an effortlessly cool result that you can take from day to night. It’s ideal for those packing light because you can mix and match endless top options with your chosen skirt.

Better yet, the midi skirt is super versatile for all seasons! Travelling in summer? Pair with a cute crop top, some sandals, and your favourite sunnies. If you’re city-breaking in the autumn or winter, simply layer up with a cardigan, jacket, and some chunky boots. Easy peasy!

Midi length not your thing? Check out our full collection of women’s skirts.

Nara Orange Sunset Stripe Midi Skirt
Nara Orange Sunset Stripe Midi Skirt

The Versatile Jumpsuit

Need something simple to ‘throw on and go’ but still wanna look cute? Look no further. If you ask us, the easiest way to look effortlessly cool is the ever-versatile jumpsuit. From chic wide-leg culottes to flattering cinched-at-the-waist wraps, there are so many styles to choose from. Plus, they’re all super comfy!

We’d recommend picking a funky pattern and let the print do the talking with minimal accessories, for a low-maintenance look. Pair with some comfy sliders or trainers, and you’re ready to stomp around the city all day long.

Black Geometric Print Wrap Jumpsuit
Black Geometric Print Wrap Jumpsuit

Jeans and a Nice Top

If it ain’t broke, don’t fix it. And this goes for wardrobe staples too. There’s a reason so many of us reach for the classic ‘jeans and a nice top’ combo, for almost every occasion. From high-waisted flares to low-rise boyfriend numbers, there are so many different jean styles on the market, and we’re obsessed with all of them. Whatever your flavour, we recommend picking your favourite pair and rotating different tops all weekend long for a new look every day.

What’s more, jeans are the easiest thing to dress up or down. Keep things casual with trainers and a cool slogan tee, and dress up with some killer heels and a cute blouse or cami.

Need some top inspo? We have endless options in our tops edit.

High Waisted Wide Leg Jeans In Medium Blue Denim
High Waisted Wide Leg Jeans In Medium Blue Denim

Now you’ve sorted all your city break looks, have you thought about your airport fit? Check out our blog on our fave airport outfit ideas and turn the plane aisle into your catwalk.

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