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Top Holidays
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Winged Boots has arrived on Shenfield High Street

News | 07 October 2025

In an era when some question the future of our high streets, we see something different. We see an opportunity to bring travel back to where it belongs: face to face, with conversations that spark possibility and personal service that no algorithm can match. That’s why Winged Boots have opened our first retail store in Shenfield, Essex.

More than just a shop, it’s a place where inspiration flows as freely as the coffee, where you can step off the pavement and into, well… Wherever you like. At Winged Boots, we believe luxury travel is about connection. To create a holiday that truly fits, we need to know you, your passions, your quirks and the stories that shape your wanderlust. Which is why the most exciting part of our new opening isn’t just the space itself, but the people waiting to greet you inside.

Allow us to introduce them...

Matt Clayden, Retail Store Manager
Matt Clayden, Retail Store Manager

Meet Matt Clayden, Retail Store Manager

With over 16 years in luxury travel, Matt has turned his global experiences into a craft of personalisation. His journey began in Austrian hotels and has since taken him from the beaches of Bali and the lagoons of the Maldives to safaris across Zimbabwe and cultural explorations in Sri Lanka. What sets Matt apart is the way he listens. He thrives on getting to know clients personally, then curating trips that feel as if they were made for them alone. Matt is also a passionate foodie, skier and safari enthusiast. His dream holiday? Chartering a private yacht around Sicily in the height of summer, glass of something chilled in hand. From Silversea cruises to road trips through Colorado, he’s built an encyclopaedic knowledge of the world’s most extraordinary escapes. Whether you’re dreaming of South African game drives or Maldivian overwater villas, Matt is the person who will make it happen. Book an appointment in our Shenfield store and start planning.

Gemma Wilson-Dines, Personal Travel Manager
Gemma Wilson-Dines, Personal Travel Manager

Meet Gemma Wilson-Dines, Personal Travel Manager

After more than a decade in the industry, including years as British Airways cabin crew, Gemma swapped aisles for itineraries and found her true calling: crafting luxury escapes rooted in insight and care. She brings first-hand knowledge from every corner of the globe; from waking up to birdsong in a tented camp on the plains of Botswana, to standing in awe of the Galapagos on an expedition cruise. Gemma is happiest when helping clients explore the world’s wilder, more soulful corners. Ask her about Kenya, Tanzania, or India and you’ll be swept into stories of wildlife, landscapes and moments that linger long after you return home. She has a gift for precision and a genuine warmth that ensures every trip feels seamless yet deeply personal. Next on her own horizon? Antarctica - proof that she’s as much an adventurer as the clients she serves. Keen to venture to the most Southern point of the world? Get your Antarctica questions answered by our expedition experts.

Winged Boots retail store
Winged Boots retail store

Why This Store Matters

Our new Shenfield home is more than bricks and mortar; it’s a statement of what Winged Boots stands for. Personal, face-to-face service. Stories swapped over a cuppa. The reassurance that your holiday is being crafted by someone who has stood on the same beaches, driven the same roads and knows how to unlock experiences you’ll never find online.

The high street isn’t fading. It’s evolving. And we’re proud to be part of its new chapter, rooted in community, powered by expertise, and ready to send you on journeys that truly mean something. Come and visit us inside today by calling us on 01277 289 777 or book your appointment now.

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Be inspired

Winged Boots:
The Lifestyle Brochure

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Blending the latest luxury travel trends, inspiring editorial and exclusive customer interviews with our curated list of the top hotels in the world, allow our brochure to spark your wanderlust.

order your copy today
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Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.