Influencer-Approved Holiday Looks You Need This Season
Holiday season is fast approaching, which may mean that your suitcase game needs an upgrade. Whether you’re heading to a sun-soaked beach, a cosy mountain retreat, or a city that never sleeps, packing the right pieces can make or break your getaway. That’s where we turn to the pros: influencers Chloe Lloyd and Josh Cuthbert, whose style isn’t just aspirational, it’s entirely achievable.
From breezy linens to softly toned staples, these style mavens offer a fresh take on what to wear away from home. We’ve sat down with them to get the inside scoop on what to pack, what to leave behind, and how to turn every holiday outfit into an Instagram-ready moment. Let this serve as a little moment of clarity in the packing chaos - soft tones, airy fabrics, and inspiration that keeps your holiday wardrobe feeling relaxed and uncomplicated.
Written By: Madelaine Law - Published: 29.03.2026
Josh's Holiday Picks
What were your go-to pieces when packing for the Maldives, and which outfits did you find yourself reaching for most during the trip?
It would have to be simple shirts - long sleeve or short sleeve. A nice fit is important too, because on holiday you don’t want to be wearing anything tight. I went for a lot of loose-fitting linen shirts and simple tees. I often reached for light, summery colours like beige, white, and navy. If I did wear something dark, I’d always pair it with light trousers to keep the look summery.
How did you style your Ted Baker short-sleeve shirts for different moments on the trip – like daytime exploring versus evenings with Chloe?
I was in the Maldives, so actually the day and night time looks were quite similar! The main difference came down to footwear. During the day, I liked wearing Ted Baker's Patterned Short Sleeve Shirt with smart white trainers. In the evening, a nice pair of suede loafers worked really well.
On a trip like the Maldives, how do you decide when to wear shorts and T-shirts versus more structured pieces like tailored trousers?
I’m not the biggest fan of shorts, to be honest, so I try to wear trousers whenever I can - especially lightweight linen ones, so they don’t feel too hot. You can’t beat a pair of tailored trousers for an evening look; they really make an outfit. That said, I do occasionally wear shorts during the day, especially if I’m out exploring the island.
Which trainers did you end up wearing the most in the Maldives, and what made them work so well for the setting?
I loved wearing the simple, smart-casual BOSS trainers. They’re perfect because they can be dressed up or down. They look great with a simple shorts-and-tee combo, and they also work well with a smart pair of linen trousers. Every man should own a nice pair of low-top, smart white trainers, in my opinion!
When you look back at your Maldives content, would you say your and Chloe’s styles naturally aligned, or did one of you set the tone for the overall holiday aesthetic?
We have very similar styles, to be honest, so we always seem to end up matching without even trying! Chloe has definitely helped me find my style over the past few years - I do feel like women know best!
Chloe's Holiday Picks
Your Maldives trip with Josh looked like the perfect ‘in-sync’ getaway - how do you approach styling as a couple? Do you plan your outfits together or let things come together more naturally on holiday?
Josh always double-checks every outfit with me before we go anywhere. I had a full 10-outfit fashion show! He doesn’t really need the help - every outfit was great - but every now and then I do have to veto the odd rogue T-shirt choice.
When packing for a romantic getaway like the Maldives, what are some of your suitcase non-negotiables?
I love a shirt dress to stay cool, and I love that it can be worn from day to night. I always look to brands like Ralph Lauren for their effortless, put-together styles. I fell in love with their tan sandals and know I’ll wear them for years to come! Cute bags are always a must, and my Tommy Hilfiger one was perfect for a getaway.
How did you style the Nobody’s Child Mia mini dress differently for daytime versus evening on your Maldives trip with Josh?
In the daytime, I’d wear it with the bag’s crossover strap and style my hair in a low ponytail.
How did you style the accessories - like your sandals and tote - to work across different outfits during the trip?
The tan sandals went with absolutely everything! They’re perfect for both day and night, and the logo detailing adds something special. The tote is great too - it has a detachable handle, which makes it easy to use at any time of day.
Your holiday content always feels effortless but polished. Do you and Josh have any tips for capturing stylish couple moments on camera without it feeling too staged?
My top tip is to use the ‘burst’ option when you take a photo. It snaps hundreds of photos instantly, so you can capture those in-between moments and get the shot much faster - without the awkward waiting!