August 10, 2023

The best shoes for city breaks

So you’re looking forward to your upcoming city getaway. But what shoes should you pack?

If you’re going on a short city break, you won’t want to take much luggage, keeping it light and easy to carry. However, you might also be planning a full day of touring and site-seeing, so you require something comfortable that still looks good on holiday.

At Cheaney, we have the best smart shoes for city breaks, from comfortable trainers for exploring to lightweight slip-on loafers to casual dress shoes for evening wear. Here, we discuss the best holiday shoes to pack for your city break, including some of the most stylish designs available at Cheaney.

Table of contents

How many shoes do I need for a weekend trip?
What shoes to wear on a city break?
What are the most comfortable shoes for city walking?
What are the best men’s dress shoes for travel?

How many shoes do I need for a weekend trip?

You don’t need to over-pack for a weekend city trip. You’re probably only taking a small suitcase and might have to walk to your accommodation. One thing you can do to lighten your load is reduce the number of shoes you take in your luggage.

Everyone needs at least one pair of smart shoes and one pair of comfortable trainers on a typical city weekend away; one to wear and one to pack while travelling.

What shoes to wear on a city break?

For city breaks, you will need one pair of casual shoes or boots for walking and exploring during the daytime, alongside some smarter shoes for going out in the evening. As long as they are comfortable you’re good to go.

What are the most comfortable shoes for city walking?

If you’re taking a city break, you’ve likely got lots of walking scheduled and site-seeing plans. The last thing you want is a poor or uncomfortable pair of shoes ruining your holiday because they’ve given you blisters or rubbed your foot. We recommend choosing a pair of lightweight and breathable trainers to keep your feet cool and comfortable while exploring.

Lightweight and flexible footwear is also essential for travelling. Whether you’re flying to your destination or taking another form of transport, lighten your luggage load with a pair of our trainers.

Our collection of contemporary trainers contains casual styles that don’t compromise comfort, perfect for dress-down outfits on holiday. From casual fashion trainers like Hallam and Kelham to our sporty-style Bannister trainers, we provide the most comfortable shoes for city breaks.

Although your main aim is to be comfortable, there is no need to compromise on style. Our stylish trainers for city walking will provide you with a fashionable look while keeping your feet comfortable throughout the day.

Browse our variety of trainer colours to suit your holiday style and wardrobe, from fresh white kicks to more casual brown and navy colourways.

What are the best men’s dress shoes for travel?

If you’re looking for smart city shoes for an evening out while on your city break that are also lightweight to carry in luggage, you can’t go wrong with a pair of loafers. They’re dressy enough for dinners and evenings out but still give you that relaxed holiday feel with their easy slip-on design.

From soft and supple suede to black calf leather, our loafer collection has a range of styles and designs. They range from casual slip-ons to more formal footwear to suit your destination and activities.

Here are few styles that we think would work perfectly as city break shoes:

Howard GV in Black Kudu Leather

The Howard is a robust loafer which blurs the line between formal and casual. Black Kudu leather from C.F. Stead is paired with Vibram’s airy Vi-Lite soles for the ultimate in slip-on comfort.

The Toby and Timothy

The Toby and Timothy models have different designs but have a common unique feature that offers convenience for your packing. The Toby is a suede penny loafer and comes in various shades, with the camel shade being the most summery. The Timothy is a suede tassel loafer, coming in three shades to suit your taste and wardrobe.

Our Toby and Timothy models are the perfect city break shoes because they are semi-lined along the apron, providing supreme comfort for the wearer. Furthermore, they feature no shank or heel and toe stiffeners, and with new flexy leather and cemented sole, these loafers can almost completely collapse, making these practical shoes to pack in a weekend bag. These loafers offer light weightlessness but are durable enough to support the wearer and provide a practical and stylish shoe to enjoy on your summer city break.

Don’t forget to pair your loafers with invisible socks to help prevent your shoes from rubbing.

City-style shoes at Cheaney Shoes

From comfortable trainers for city site-seeing to laid-back loafers for the evenings on your city break, we have all the shoes you need to take on your getaway.

However, if you’re visiting a city for a more formal occasion, we recommend glancing at our men’s city shoes. These sleek and sophisticated city-style shoes in black calf leather are the ultimate hallmark of refined taste, perfect for any formal occasion in the city.