Destination Fashion: What to Wear Where

Before you set off on your holibobs, make sure you’ve packed the right attire for the location. Gentlemen, this is your guide to destination fashion.


Whether you’re posing for a picture by the pool or visiting one of the seven wonders of the world, taking care of your appearance is essential. After all, your holiday snaps will last a lifetime.


From Cuba to India, here’s your essential guide on what to wear where.


What to wear on holiday in Cuba?


Slick back that hair and transport yourself to the 1950s. Cuba might be the most retro destination in the world, with vintage cars a common vehicle to ride around town. Its vibrant culture and sizzling energy make Cuba a great place to visit.


So, if you’re ready to order a mojito and dance the rumba, make sure you pack these holiday essentials:

  • ShirtParlez offers a Castries Cuban shirt in dusty blue. The classic box fit and lightweight, breathable cotton cut make it perfect for those hot days and cool Havana nights.

  • Hat – The Cuban Canotier Hat, also known as a Boater, Pork pie or Gondolero, is a vintage headpiece supporting formal and informal. A signature hat for the refined Cuban Gentlemen between 1914-1940.

  • Shoes – Cuba is known for not having the smoothest roads. But you also want something you can dance in. Go for comfort, durability, and retro style. Our Watson Brogues in black or brown fit the bill, with guaranteed Goodyear Welted construction and full leather lining.

What to wear on holiday in Thailand?


Whether you’re partying down Khaosan road or chilling nicely on an island beach, Thailand will keep you on your toes! If you want to know what to wear on holiday in Thailand, you better be prepared for anything!

  • Swim shorts – On a boat ride or just out exploring, Thailand offers clear blue waters around all corners, so get ready to take a dive. Riz provide ethically made swim shorts designed to be worn all day, at the beach or in the bar. The Braunton addition is suited stylistically and practically for a Thai adventure.

  • Vest – It’s not every day you get to wear a vest. However, the laid-back culture of Thailand shows there’s no better place to sport a vest and sell free tickets to the gun show.

What to wear on holiday in Cornwall?


Arguably the host of the most dramatic coastal scenery in the UK. Cornwall remains the number one holiday spot in England. Where else to take a pew, order a local pint of ale and enjoy a traditional Cornish pasty?

  • Jacket – Always prepare for the unexpected when holidaying on home shores. Don’t be too optimistic and expect only sunshine. A versatile jacket is a must. The Eddie Bauer Downlight Jacket is an ideal match with a durable polyester shell to shed moisture. This ultralight, ultrawarm and ultra-compressible comfort jacket is windproof to keep you warm or cool, whatever the weather.

  • Jeans – To accompany this versatile jacket, try some comfortable jeans to balance the look.

What to wear on holiday in Greece?


Greece is notorious for its relaxed culture, where nothing can’t wait till tomorrow. In a country where there is no rushing around, a comfortable T-Shirt and shorts are what to wear on holiday in Greece.

  • T-shirt – Made from organic cotton, the Polar Bear Paddleboard T-shirt from Rapanui Clothing is an ideal way to stay comfortably relaxed and project positive, chilled, and light-hearted vibes.

  • Shorts – Compliment this laidback T-shirt with some shorts to match. Perhaps even a simple, smart, and plain style to bring harmony to the overall look and be suitable for dinner.

What to wear on holiday in Italy?


No one is allowed to go to Italy without taking advantage of the incredible food on offer. This is why Italian holiday attire revolves around ultimate style and comfort when dining.

  • ShirtTentree’s Hemp Short Sleeve Button Up is stylish, lightweight, and breathable in warm weather. Made from hemp and recycled polyester this versatile garment can also accommodate a range of jackets in cooler climates.

  • Shoes – Italy is renowned for its class, charisma, and passion for fashion. A pair of Percy Stride’s Two-Tone Oxfords will ensure you’re in keeping with the style maestros of Milan and Rome.

What to wear in India on holiday?


The options in India are endless, from hiking in the Himalayas to interrailing across vast stretches of the country. What to wear on holiday in India should be reliable, versatile, and comfortable.

Top tip – If you’re visiting the Taj Mahal, keep your Percy Stride shoes in the hotel. You have to remove your shoes on arrival, and theft isn’t uncommon.
  • Trousers Patagonia provides light, comfortable and quick to dry 100% recycled nylon Sandy Clay Pants. These trouser promises to provide the versatility required for any climate and travelling day-to-day.

  • Henley – To complement the trousers, a suitable Henley cut shirt is both stylish and nonchalant dependent on the situation. No Nasties provide an athletic fit Cayenne Henley shirt. Built for longevity and proudly made from 100% cotton in India.

What to wear on holiday in Spain?


Spain is a popular destination with us Brits and what to wear depends on the time of year and location. The Spanish are masters of the smart-casual style, for both warm and cool climates. Here we combine a casual T-shirt and smart trouser combo to encapsulate their cultural trait.

  • Trousers Armedangles fair traded organic cotton light sand beige chino trousers are sleek and minimalist, perfect with a T-shirt and white trainers.

  • T-shirt – Combine these chinos with a Kitty Wear Galactic Blue T-shirt to establish that smart casual Spanish style.

What to wear on holiday in Iceland?


Figuring out what to wear on holiday in Iceland is a matter of keeping warm. In this beautiful destination, you’ll want to make the most of the outdoors. However, you’ll need to wrap up to ensure you enjoy the aurora borealis in comfort.

  • Jacket – Italian brand, Save the Duck provide the Donald coat. Promising to keep you warm with high-density nylon fabric, this coat also guarantees to be light and fluffy. Ideal for hiking and exploring the Icelandic landscape.

  • Jumper – A coat won’t be enough to stay warm in the Icelandic climate. You’ll need a thick jumper underneath. For comfort, thickness and style, you can’t beat a classic Aran Jumper.

  • Socks – Don’t forget to keep your feet warm. Invest in some ski or thermal socks. You’ll thank me when you get there!

What to wear on holiday in Dubai?


Known for its affluent community, you’ll want to fit in glamorously but also culturally. It’s best to avoid exposing too much flesh as a way of respect. Light, breathable, and smart attire will be on the billing for what to wear on holiday in Dubai.

  • Shirt – Asket offers a natural choice for hot climates with their white 100% linen shirts. This shirt is breathable, smart and respectful of Dubai’s culture.

  • Shoes – Seeing as Dubai was built on a dessert; some dessert boots would not go amiss for outside activities. Percy Stride’s collection of George Chukka boots come in Sand, Chocolate, Blue and Plum. A perfect match for the sandy environment.

Destination fashion ready


Across the world, each culture has its own unique fashion identity. It takes a refined gentleman to pay homage to these separate cultures and take inspiration for his own sense of style. From Thailand to Iceland, there is some stylistic influence waiting to be shared and enjoyed.


If you want a pair of comfortable, durable, and luxurious footwear to take on your travels, please visit Percy Stride for the full range of footwear and accessories.

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