Which Shoes to Pack for a Holiday (and Which to Leave at Home)
Written by Artemis Clo
Deciding what shoes to pack for a holiday is where most suitcases go wrong: shoes are heavy, bulky and oddly tempting to over-pack. The answer for nearly every trip is three well-chosen pairs. Here is how to choose them, and which ones to leave by the front door.
The three-pair rule: what shoes to pack for a holiday
Almost any holiday of up to two weeks can be covered by three pairs, each with a clear job.
- The walking pair. Trainers or comfortable flat shoes you can wear for a full day of exploring. Wear these on the journey.
- The warm-weather pair. Sandals or slides for the beach, the pool and hot afternoons. Choose ones you can also walk in for an hour, such as walking sandals with touch straps.
- The evening pair. Something a little dressier that works with every evening outfit you are packing, ideally in a neutral or a colour that ties your outfits together.
The trick is that each pair must go with most of what you are bringing. If a shoe only works with one dress, it is not coming. Browse the sandals with your holiday wardrobe laid out on the bed, and you will see quickly which ones earn their place.
Sandals to consider
A few pieces that fit what you have just read.
Orthopaedic Walking Sandals with Touch Straps
Orthopaedic Cross-Strap Platform Slides, Woven Band
Orthopaedic Cork-Effect Platform Wedge Sandals
Matching your shoes to the kind of holiday
A beach holiday
Here sandals do the heavy lifting. A pair of slides for the beach, a pair of sandals you can walk in, and a light evening shoe usually cover it. A cork-effect platform wedge sandal can do double duty from a lunch in town to dinner on the terrace. On pebbly beaches, add water shoes; they weigh almost nothing.
A city break
You will walk more than you think, often ten or fifteen thousand steps a day on cobbles and stairs. Make the walking pair your priority: trainers or flat shoes that you have already worn for long days at home. A pair of lace panel trainers with polka dots looks perfectly at home in a café as well as a museum. For ideas on a cooler break, see our guide to what to wear in Paris in autumn.
A countryside or walking holiday
Swap the sandals for something with a proper grip. Walking shoes or sturdy trainers for the paths, a pair of ankle boots if the weather is uncertain, and one comfortable flat pair for the pub in the evening. Pack a spare pair of socks for each day, and a plastic bag for muddy soles on the way home. If rain is likely, a quick spray of waterproofing before you leave is time well spent.
A cruise or a mixed itinerary
Think in terms of days ashore and evenings on board. Walking shoes for excursions, sandals for the deck, and an evening pair that suits the dress code. Our notes on what to wear on a cruise go through each part of the day.
Which shoes to leave at home
Some shoes rarely earn their space in a suitcase. Be honest with yourself about these:
- Brand-new shoes you have not worn yet. A holiday is the worst place to discover that a pair rubs. Wear them at home first; our guide on how to break in new shoes gently explains how.
- High, narrow heels. Cobbles, sand, gravel paths and boat decks all conspire against them. A low block heel or a wedge gives you height with far more ease.
- The just-in-case pair. If you cannot name the evening you will wear it, leave it behind.
- Heavy boots for a warm trip. If you need them for the journey home in winter, wear them on the plane.
Packing shoes for a holiday so they arrive in shape
A few minutes of care keeps your shoes and your clothes in good order.
Put each pair in a shoe bag or a clean cotton pillowcase to keep the soles off your clothes. Stuff the toes with socks, underwear or a phone charger: it saves space and helps the shoes keep their shape. Place them at the bottom of the case, near the wheels, with heels against the sides, so they do not crush anything delicate.
Wear your bulkiest pair on the journey. Slip a pair of sandals into your day bag if you are flying somewhere warm, so you can change on arrival. A roomy straw-look tote bag with long straps doubles as a beach bag once you are there, and our guide on how to pack a carry-on for a week covers the rest of your case.
Next, from our bags
Something from a neighbouring rail, for the same moment.
Woven Straw-Look Tote Bag with Long Straps
Woven Straw-Look Crossbody Bag, Slouchy Shape
Leather-Look Crossbody Bag with Wide Strap
Your questions, answered
What shoes should I wear on the plane?
Your bulkiest pair, ideally one that slips on and off easily at security. Many people find their feet feel a little fuller after a long flight, so a pair with some give, such as trainers with laces you can loosen, is kinder on the way home.
Can I take shoes in hand luggage?
Yes, shoes are fine in hand luggage. Put them in a bag of their own so the soles stay away from your clothes, and wear your heaviest pair on the plane to save space and weight.
Are sandals smart enough for evenings on holiday?
In most warm destinations, yes. A sandal with slim straps, a low wedge or a metallic finish looks dressy with a midi or maxi dress. If you have booked a smart restaurant, check its dress code before you pack.
Do I need water shoes for a beach holiday?
They are handy on pebbly or rocky beaches and around rock pools. On soft sand, a pair of slides or flip-flops is usually enough.
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