What To Wear For Every Holiday

Posted on: August 14th, 2025 – Words by Tobias Wightman

'Tis the season that comes but once a year. No, not that one. We’re feeling jolly, but it’s the sunshine that’s putting a smile on our faces. With summer in full swing, it’s officially time to pack your bags and follow the sun wherever it leads.

Of course, no two holidays look the same. Every trip comes with its own vibe - and its own menswear dress code - so your suitcase should reflect that (aside from the inevitable overpacking of underwear, of course). So, think of this outfit guide as your trusty co-pilot, here to help you dress for wherever your flights and itinerary may take you.

The Rural Explorer

Holidays are for relaxing - unless you’re the type who’d rather rack up steps than lounge poolside. You know who you are. And fair enough. Just dress for adventure.

Our relaxed-fit Milton brings all-day comfort and a pop of colour from its getaway graphic - perfect for channelling your wanderlust. Pair it with navy linen Kurt shorts for a look built to explore. For racking up those miles, the Flower Mountain YAMANO 3 trainer, with its toothed tread sole, is the ideal walking companion. And if you insist on being out in the sun all day, the Farrell cap, Eltham sunglasses, and Sloane scarf have you covered. The perfect fit for a holiday excursion.

The Destination Wedding

This isn’t your average “grab a suit and go” affair. Destination weddings demand fabrics that breathe, colours that stand out without stealing the spotlight, and footwear ready for everything from cobblestones to sandy aisles.

Our pick? The matching rust Fintry jacket and Alp trousers - a linen two-piece that mirrors golden hour hues and keeps you from becoming a sweaty mess long before the vows. Layer it with the ecru seersucker Didcot for an extra hit of breathability. As for footwear, we’re not having you in sandals. The black leather derbies from S.T. Valentin strike the perfect balance - smart enough for the occasion, comfortable enough for the dance floor. And because weddings (especially in the heat) can be a marathon, a quick spritz of our Magna fragrance will keep you smelling as good as you look and the Fulham sunnies will hide the “one glass too many” sparkle in your eyes.

The Dinner Date

This one’s for the foodies, the ones who breeze through check-in with luggage, passport, and knives and forks at the ready. Chasing the best dining spots takes good taste - so naturally, your outfit should meet the same standard.

For evenings out, you can’t go wrong with all black. Whatever the formality, it’s a timeless, foolproof choice. But an all-black look from Wax is never basic. Our cotton-linen Didcot adds texture and contrast with its appliqué design, plus a dose of breathability - because yes, it’s still warm after dark. Pair it with our black linen Kurt trousers; their relaxed fit and drawstring waist strike the perfect balance between comfort and polish. Speaking of, the leather loafers from S.T. Valentin finish the look perfectly. And before you head out, a couple of sprays of our Holm scent will seal the deal.

The Bar Hopper

Fine dining can wait - there are too many bars to hit and your mate’s already got the next round. You’re here to soak up the local culture… even if that culture comes with a heavy head the following morning. But a man of simple tastes still deserves to dress for the evening’s events.

Let’s keep it casual - yet elevated. Start with the Porto crochet shirt: its bold blue hues make it a summer getaway essential, and the knit construction keeps things breezy as you hop from place to place. Add a Montague vest for easy layering, then stick with the ecru palette - a bold move, but we trust you - and pull on a pair of loose-fitting denim. To finish your bar-to-bar look, you’ll need two holiday staples: a solid pair of black sandals and our matching black Eltham sunnies - with drink in hand, naturally.

The Boat Trip

For the seafaring types - by which we mean anyone booked on a holiday boat trip with families you’ve never met and will never speak to again - here’s what to wear. The answer is, not a lot. But, what you wear needs to be practical.

Let’s start with the essentials - swimming shorts. Our Brockwell silhouette comes in three options: blue, black, and our pick for the occasion, a black geometric print. You’ll be in the sun all day, so a cover-up is a must. A crisp linen shirt is the perfect choice, and on a casual boat trip, a few creases only add to the carefree vibe. Finish it off with the right accessories: our Spencer cap and Eltham sunglasses to shield you from the sun, and a classic pair of slides so you’re ready for a laid-back stroll wherever the boat drops anchor.

The City Break Stroller

Itinerary in hand, you’re ready - armed with a list of must-try food spots, cultural gems, and the “best coffee in town” courtesy of a TikTok you half-remember. For all those adventures, you’ll need an outfit that can keep up.

The bold Dorset shirt does the talking - bright enough to catch the light, breezy enough in its crochet knit to keep you cool as you wander. Layer it over a crisp Montague vest for a laid-back base, and pair with Dalston denim shorts for effortless off-duty style. Striped Thorpe socks and classic white trainers will keep you comfortable as your step count climbs, while the Savona sunglasses add the perfect touch of shade for people-watching over an espresso.