What to Wear on a Walking Holiday (Practical & Stylish)

Walking holidays are about more than just covering miles. They’re about slowing down, immersing yourself in stunning landscapes, and feeling the joy of movement. Whether you’re wandering through the flower-filled meadows of the Alps, strolling from village to village in Tuscany, or following ancient trails in the UK, your experience is shaped by how comfortable and confident you feel.

That’s why what you wear on a walking holiday matters. The right clothing keeps you comfortable in changing weather, supports your stride, and yes - lets you look good when you pause for a well-deserved cappuccino in a little mountain café.

If you’re planning a trip, or simply dreaming of your next adventure, this guide will help you pack practical, stylish walking holiday essentials for both men and women.

The Golden Rules of Walking Holiday Clothing

Before diving into specifics, here are three key principles to keep in mind:

1. Layering is everything – Weather can shift quickly, especially in mountain regions. Lightweight layers let you adjust on the go.
2. Comfort meets confidence – You want fabrics that move with you, breathe well, and dry quickly, but that also look polished when you’re off the trail.
3. Less is more – Packing smart doesn’t mean overpacking. A few versatile, mix-and-match pieces will serve you better than an overstuffed suitcase.

For Women: Functional, Feminine, and Ready for Adventure

Walking holidays call for clothes that balance practicality with effortless style. Here’s what to pack:

Tops

• Moisture-wicking base layers – Opt for breathable, quick-dry T-shirts or tanks in neutral shades (think grey, navy, or soft earth tones).
• Lightweight long-sleeve shirt – A button-up linen or technical fabric shirt is perfect for sun protection while still looking chic.
• Warm mid-layer – A merino wool sweater or light fleece for cooler evenings.

Bottoms

• Walking trousers or leggings – Choose stretchy, water-resistant trousers or supportive leggings. Bonus if they’re stylish enough for dinner after your walk.
• Convertible trousers – Zip-off options can be lifesavers in fluctuating climates.

Outerwear

• Packable waterproof jacket – Lightweight but reliable; a sleek cut keeps it flattering.
• Windbreaker – For breezy coastal or alpine routes.

Footwear

• Sturdy walking shoes or boots – Go for comfort above all else. A neutral style pairs well with casual outfits.
• Casual flats or sandals – Perfect for village evenings.

Extras

• Scarf or wrap – Doubles as a stylish accessory and practical warmth.
• Wide-brimmed hat – Adds flair and sun protection.

💡 Pro tip: Pack in a cohesive color palette so everything mixes and matches easily.

For Men: Smart, Rugged, and Always Comfortable

Men’s walking holiday attire should feel just as good at the pub as it does on the trail. Here’s how to keep it sharp and practical:

Tops

• Technical T-shirts – Breathable, quick-dry options that don’t cling. Neutral or earthy tones work best.
• Collared walking shirt – A short-sleeve or roll-tab long-sleeve shirt looks polished for post-walk meals.
• Mid-layer fleece or pullover – Lightweight but warm.

Bottoms

• Walking trousers – Stretchy, durable, and water-resistant. Slim-fit styles keep it modern.
• Shorts – Comfortable, quick-dry shorts for warmer climates or afternoon strolls.

Outerwear

• Lightweight rain jacket – Choose a minimalist design that layers well.
• Softshell jacket – Ideal for unpredictable mountain conditions.

Footwear

• Hiking shoes or boots – Prioritize fit and support; neutral designs pair with casual evening wear.
• Casual sneakers or loafers – For relaxed evenings in town.

Extras

• Stylish cap or hat – Keeps the sun off while looking sharp.
• Lightweight scarf – A versatile, European-inspired touch.

Pro tip: Choose clothing with technical fabrics that look like everyday wear—comfort without sacrificing style.

Style Meets Your Next Adventure

On a walking holiday, your clothing becomes part of the experience. It’s about feeling free to wander, confident in your look, and prepared for every moment; from standing at a mountain pass to sipping wine in a village square.

When you pack with both practicality and style in mind, you’ll find yourself enjoying the journey even more. And if you’re not booked yet, perhaps now’s the time to imagine yourself lacing up your walking shoes, ready to step into that next adventure.

Explore our collection of self-guided and small group walking holidays - where comfort, culture, and breathtaking trails await.