.png.png?timestamp=2025-12-14T00:00:00+00:00 "Aquila Pty Ltd")
18 Nov 2025
What To Wear On Your Summer Trip
Your flights are booked, your itinerary is stacked, and it's now time to start thinking about what to wear on your summer holiday. Regardless of your suitcase weight limit, we have an easy guide to decide what shoes will be the most versatile to take on your travels this summer.
Leave the Chelsea boots on the shoe rack and lean into lightweight, stylish summer shoes. Every guys needs a few of these in the wardrobe, and the trick is to pick shoes with some versatility. Got a pair of leather loafers? Perfect! You can wear those to a barbecue or a rooftop bar. How about some espadrilles? Those look great from the beach to the pub for dinner.
In this article, we’re going to break down some of the more common summer shoes, and where (and how) to wear them.
The Beach
Lean into light, breathable styles when you’re by the water. While thongs cover the basics, woven sandals or espadrilles instantly lift any coastal outfit. The JETTY's pair effortlessly with relaxed cotton shorts for a morning café stop, offering an easy slip-on option with texture and warmth. For a Riviera-inspired feel, the PANAMA Espadrilles are a perfect choice; compact to pack, soft underfoot and ideal for moving from beach to late-afternoon drinks or a casual seaside dinner.
The Pool
For lazy afternoons by the pool, you want a lightweight slide shoe. Our black leather WEAVER looks great with navy shorts and a white crew tee. The trick with sandals & pool slides is comfort and durability. They’re designed to be kicked on, kicked off, and thrown in a duffle bag. Don’t be too precious about them.
The Rooftop Bar
The Fancy Restaurant
For a high-scale restaurant (the kind with tablecloths and a dress code), it’s worth leaving the casual slip-ons behind. A polished pair of ELIAS Tassel Loafers brings a warm, elevated finish to your outfit — ideal with cuffed tan chinos and a long-sleeve cotton shirt, sleeves rolled for comfort. If you prefer something more understated, the DARTMOUTH Loafers offer a clean, versatile look that works beautifully with tailored dress shorts and a crisp white linen shirt. Whichever you choose, stick to invisible socks for comfort and breathability; going fully sockless isn’t ideal for premium leather, especially on warm nights.
The Road Trip
For the summer road trip, it has to be a pair of quality leather driving shoes. They’re just a natural fit. Even if you’re not the actual one doing the driving, there’s something indefinably classy about a pair of DECO 2.0 moccasins or CRUZ suede driving shoes. They add an instant dose of retro style to any casual ensemble. Again, don’t overthink the styling here: some cotton chino shorts or khaki linen shorts are a great match, along with a crew tee and short-sleeve shirt. Bonus: driving shoes are some of the most comfortable shoes going around, which makes them perfect for winery walks and browsing country towns.
The Summer Wedding
Wedding dressing in warm weather is all about breathable sophistication. Loafers remain the most versatile choice: pair EMILIO Penny Loafers with a navy or charcoal suit for a grounded, classic look, or opt for the ROME Penny Loafers with biscuit or sand tailoring for lighter, summery tones. If you prefer lace-ups, RICO Lace-Up Shoes offer a polished alternative that still feels relaxed enough for outdoor ceremonies. Each brings comfort and style without the heaviness of traditional dress shoes - ideal for long afternoons celebrating in the sun.