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Men's Holiday Shoes

Discover our collection of men's holiday shoes, designed to suit any and every summer getaway. Whether you're lounging on the beach, exploring sun-soaked streets, or heading out for dinner, our men's holiday shoes will keep you comfortable through every moment of your trip.


Looking for more warm-weather staples? Explore our full range of men's summer footwear - from breathable men's slip-on canvas shoes to smart-casual loafers made for holiday adventures. No matter if you’re packing for a beach break or a city escape, there’s something here for every destination.


And if you're after something beyond your suitcase essentials, take a look at our complete collection of men's shoes. With free next-day delivery available, it’s easy to get set for summer- and whatever comes after.

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Lambretta Pinball Mens Tan Casual Trainer (Click For Details)
Brown
White
NOW £24.99
was £29.99 
RRP £75.00
Lambretta Pinball Mens Tan Casual Trainer
SAVE
Original Penguin Steadman Mens White Trainer (Click For Details)
White
Tan
NOW £29.99
was £34.99 
RRP £70.00
Original Penguin Steadman Mens White Trainer
Star ratingStar ratingStar ratingStar ratingStar rating
SAVE
Original Penguin Giovanni Mens Grey Casual Shoe (Click For Details)
Grey
Blue
£34.99
RRP £75.00
Original Penguin Giovanni Mens Grey Casual Shoe
Star ratingStar ratingStar ratingStar ratingStar rating
Web only, this product cannot be bought on the high street
Skechers Cavell Hensley Mens Brown Lace Up Shoe (Click For Details)
£54.99
Skechers Cavell Hensley Mens Brown Lace Up Shoe
Star ratingStar ratingStar ratingStar ratingStar rating
Ben Sherman Chase Mens Tan Casual Shoe (Click For Details)
Tan
White
£39.99
Ben Sherman Chase Mens Tan Casual Shoe
Star ratingStar ratingStar ratingStar ratingStar rating
Web only, this product cannot be bought on the high street
Skechers Slip Ins Garza Clive Mens Blue Vegan Shoe (Click For Details)
NOW £49.99
was £69.99  then £59.99 
Skechers Slip Ins Garza Clive Mens Blue Vegan Shoe
Star ratingStar ratingStar ratingStar ratingStar rating
SAVE
Cushion Walk Declan Mens Casual Tan Slip On Shoes (Click For Details)
£29.99
Cushion Walk Declan Mens Casual Tan Slip On Shoes
Star ratingStar ratingStar ratingStar ratingStar rating
Stone Creek Gabriel Mens Brown Casual Shoe (Click For Details)
£29.99
Stone Creek Gabriel Mens Brown Casual Shoe
Star ratingStar ratingStar ratingStar ratingStar rating
Original Penguin Steadman Retro Mens Navy Trainer (Click For Details)
Blue
White
£34.99
RRP £75.00
Original Penguin Steadman Retro Mens Navy Trainer
Star ratingStar ratingStar ratingStar ratingStar rating
Web only, this product cannot be bought on the high street
Original Penguin Giovanni Mens Navy Casual Shoe (Click For Details)
Grey
Blue
£34.99
RRP £75.00
Original Penguin Giovanni Mens Navy Casual Shoe
Web only, this product cannot be bought on the high street
Original Penguin Steadman Retro Mens White Trainer (Click For Details)
Blue
White
£34.99
RRP £75.00
Original Penguin Steadman Retro Mens White Trainer
Web only, this product cannot be bought on the high street
Cushion Walk Ant Mens Navy & Brown Boat Shoe (Click For Details)
Blue
Tan
£29.99
Cushion Walk Ant Mens Navy & Brown Boat Shoe
Star ratingStar ratingStar ratingStar ratingStar rating
Cushion Walk Ant Mens Tan Casual Boat Shoe (Click For Details)
Blue
Tan
£29.99
RRP £34.99
Cushion Walk Ant Mens Tan Casual Boat Shoe
Star ratingStar ratingStar ratingStar ratingStar rating
Comfy Steps Ramsay Mens Tan Fisherman Shoe (Click For Details)
NOW £19.99
was £29.99 
Comfy Steps Ramsay Mens Tan Fisherman Shoe
Star ratingStar ratingStar ratingStar ratingStar rating
SAVE
Lambretta Pinball Mens White Casual Trainer (Click For Details)
Brown
White
£29.99
RRP £75.00
Lambretta Pinball Mens White Casual Trainer
Star ratingStar ratingStar ratingStar ratingStar rating
Web only, this product cannot be bought on the high street
Cushion Walk Greg Mens Grey Easy Fasten Shoe (Click For Details)
Grey
Brown
£29.99
RRP £34.99
Cushion Walk Greg Mens Grey Easy Fasten Shoe
Star ratingStar ratingStar ratingStar ratingStar rating
Ben Sherman Chase Mens White Casual Shoe (Click For Details)
Tan
White
£39.99
Ben Sherman Chase Mens White Casual Shoe
Web only, this product cannot be bought on the high street
Hush Puppies Madden Mens White Leather Shoe (Click For Details)
White
Tan
Brown
£49.99
RRP £75.00
Hush Puppies Madden Mens White Leather Shoe
Web only, this product cannot be bought on the high street
Relife Stephen Mens Navy Easy Fasten Shoe (Click For Details)
NOW £29.99
was £39.99 
Relife Stephen Mens Navy Easy Fasten Shoe
Star ratingStar ratingStar ratingStar ratingStar rating
SAVE
Cushion Walk Greg Mens Brown Casual Shoe (Click For Details)
Grey
Brown
NOW £24.99
was £29.99 
Cushion Walk Greg Mens Brown Casual Shoe
Star ratingStar ratingStar ratingStar ratingStar rating
SAVE
Hush Puppies Madden Mens Tan Suede Shoe (Click For Details)
White
Tan
Brown
£49.99
RRP £75.00
Hush Puppies Madden Mens Tan Suede Shoe
Web only, this product cannot be bought on the high street
Osaga Rice Mens White Casual Shoe (Click For Details)
£29.99
Osaga Rice Mens White Casual Shoe
Hush Puppies Madden Mens Coffee Leather Shoe (Click For Details)
White
Tan
Brown
£49.99
RRP £75.00
Hush Puppies Madden Mens Coffee Leather Shoe
Web only, this product cannot be bought on the high street
Ben Sherman Curve Mens White Casual Shoe (Click For Details)
£39.99
Ben Sherman Curve Mens White Casual Shoe
Web only, this product cannot be bought on the high street
Show All
43 products from £12.99 to £59.99.
Our collection of men's holiday shoes

When it comes to men’s holiday shoes, there’s a great mix of styles to elevate your look and keep things comfortable. From classic loafers with a touch of sophistication to casual boat shoes that channel laid-back vibes, there’s something for every occasion. Breathable trainers are ideal for warm days, while slip-on shoes offer an easy, relaxed option that’s perfect for casual strolls on the beach.


Get ready for Summer with our men's holiday shoes

Now for the holiday outfit inspiration. Pair your holiday loafers with a crisp white linen shirt and tailored shorts for a smart-casual look. Try matching a pair of canvas shoes with a lightweight tee and relaxed chinos, or keep it simple with a pair of slip-ons, cargo shorts and a vest for an effortless holiday look.


Men's holiday shoes, perfect for every trip

Ready to find your perfect pair? Explore the full range of men's shoes and enjoy great prices, reliable styles, and free next-day delivery, just in time for your next getaway.


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2,797 of our products have an average rating of 4.5 from over 74,918 reviews.