How To Dress To Impress When You're Away On Holiday

Holidays are for relaxing but that doesn't mean you can walk the streets in Speedos.

For some of you lucky bastards, January is all about lying by the pool and forgetting you are gainfully employed in a miserable office with a forty-minute commute somewhere.

But while it’s normal to enjoy kicking back on a beach somewhere, we’re a little disappointed that annual leave in the tropics has become carte blanche to dress like you’re hungover as fuck and answering the door to Ubereats.

Hopefully, you’re a distinguished critic of the Bintang-singlet crowd like us. But if not, we’ve put together a quick guide for how to dress on holidays, because we all know that the world deserves much, much more than the brutally average sartorial efforts of the average Aussie punter abroad.

Pack The Essentials (And Be Ruthless About It)

Travel light like a nomad…a stylish nomad

Luggage problems almost always kill the holiday buzz, and it usually starts with overpacking.

You can enjoy a solid weeklong holiday with a well-organised messenger bag (if you’re happy to wash the basics for repeated use). Don’t be the moron that packs thirty kilos of useless crap and whinges the whole way about how sore you get from carrying them everywhere, or how much it sucks to wait for the baggage claim area to spit out your gear.

Holidays aren’t for waiting in line to check in luggage and then pay a ridiculous premium for it. They’re definitely not for mourning a lost bag that jettisoned somewhere over the Pacific Islands. Pack light, be ruthless, and you’ll have an easier time dressing on holiday. We’ve even got a guide for you on how to do it right.

Make Your Hotel & Resort A Bintang-Free Zone

Think linen before singlets

Australians have cultivated a unique reputation for taking it really, really, easy when it comes to their wardrobe overseas. And it sucks.
You probably get annoyed when blokes on a footy trip come to town looking like ratbags, or when festival goers assault the local bakeries with abominable style decisions. The locals probably feel the same way about tourists.

So instead of a ratty singlet, wear a relaxed linen shirt. They’re just as comfortable and will get you through the door in upscale parts of town. Boardies are a necessity but pack chino shorts too. The point is, other Australians might dress to the lowest common denominator – but it doesn’t mean you need to as well.

Bring One or Two Nice(ish) Outfits

Ensure it’s lunch or dinner venue appropriate

It’s a time to kick back, relax, and tan, but you will still probably end up going to a restaurant or (if you’re really boring) going shopping in the nicer parts of town. It pays to pack at least one smart backup look – chinos, a shirt, and loafers – if you plan to hit the tiles or check out some of the prestigious joints in town.

Looking the part shows respect for the local area and inhabitants and can open opportunities you certainly won’t receive if you’re wearing a singlet that hasn’t been washed in three days and a pair of boardies you stole at schoolies back in 2005.

Up Your Sandal & Sneaker Game

Thongs are comfy and part of the Australian cultural experience, but they’re rarely (i.e, never) flattering and pretty rough on your feet if you have a long trek at some point. Replace them with sandals (not the shitty old-person kind that “massage” your feet) and you’ll have a better holiday for it.

Sandals have matured far beyond their reputation as footwear for racist baby boomers and retired European tourists on their first trip to Australia. Find something that doesn’t look like your One-Nation voting uncle’s crocs or hipster Birkenstocks and you’ll be able to transition from the pool to local bars without any fuss or disapproving stares from the locals.

If you need help we did a recent feature here on sandals that pass the DMARGE sartorial sniff test.

But Leave The Big Stuff Behind

Saint Laurent ain’t Laurent on holidays

While you might go out to a fancy restaurant or club at some stage during your time off, you’re still in an unfamiliar location.

Holidays bring disruption to routine, encounters with weird backpackers in your hostel, locals you forgot to tip, and generally an uncontrolled environment where things can get lost, damaged, or pinched. Generally, you should only bring clothes or accessories on holiday that won’t cause a nervous breakdown if you lose them.

That’s not to say people outside Australia are more likely to flog your belongings but in general, holidays bring a bit of extra chaos and the last thing you need is a lost afternoon of panic searching under the deckchairs and hostel beds for a missing watch or ancestral bling. Leave the high-end luxury shit at home, you’ll thank us later.

Don’t Forget Your Skin

Remember: You’re not invincible like Bond

Let’s face it, holidays can put stress on your body. Rubbish food, excessive sun, and dodgy cocktails all contribute to not looking your best (remember kids, ‘sun-touched’ isn’t a compliment).

It’s important to maintain a regular skincare routine when you’re making the most of your time off. All it takes is a small tub of moisturiser and a hydrating cream in your bag. If that’s too much to ask, you can probably buy something while you’re there.

And whatever you do, blokes, always wear sunscreen. Your narcissistic Instagram stories of #blissful Bali beaches might be a bit of a joke, but looking like a shrunken op-shop leather handbag, or getting skin cancer, is not.

RELATED: After Sun Skin Care Essentials

Brands You’ll Want On Your Next Holiday



Orlebar Brown


J Crew


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