I started writing this newsletter when I was freshly home from Mexico - tanned, relaxed, ready to dive into 2026 like I had the turquoise waters of the Pacific. That version of me is long gone, but let this serve as a memory of the person I once was - a smug alter ego who wants to share a few tips on what to wear whilst being the most insufferable (but hottest) version of yourself.
I have a working theory about holiday style. I think it can be more or less categorised into the below buckets:
Me, but on holiday
This is the person that wants to keep hold of their existing style, but simply adapts it to the climate and surroundings they’re in. In the extreme, these are the ones who refuse to bend their wardrobe to the will of a new destination - think jeans at the beach, or Mariah Carey sinking her stilettos into the sand.
New me on holiday
These are the people who shop especially for a holiday. They’re ordering floaty resortwear and putting together looks, ready to step into a new vacation version of themselves. They also buy things at their destination - shopping for skimpy bikinis, airy cheesecloth dresses or a cap from the merch selection at their boutique hotel.
Leave me alone on holiday
This person views vacation as a chance to fully switch off, and this extends to what they wear. That doesn’t mean they look bad, it just means that any part of getting dressed that feels fussy, or like ‘work’ is abandoned in pursuit of rest and relaxation. Comfort and practicality take centre stage here; clothes are simply a vessel for the activities at hand, whether that’s functional gear for outdoor adventures, or super easy pieces for lolling on the beach.
I’d say I’m a mixture of 1 and 3. I still want to feel like I’m channeling a vibe, or that when I tell someone I work in fashion they won’t immediately think “in what universe?”
But I also want to be liberated from the pressure to pull a look. Much of what I usually wear is dictated by a need (and a desire) to look stylish, so I view holidays as a chance to switch off this brain function. Let it rest and restore, and return with (hopefully) better outfits.
I felt pretty happy with my packing formula for this trip - it’s the closest I’ve ever come to a capsule wardrobe, and one that all fit neatly into one carry-on! Here’s what I brought:
1 x pair of light pants
This was the first time I bought new clothes especially for a holiday (ok so a sliver of no.2 energy). A pair of black Havaianas flip flops (classic, useful), and a pair of CouCou’s ‘The Pant’ in cotton voile. The latter weigh nothing, but don’t feel as exposing as a pair of shorts.
1 x airy white shirt
This is a vintage one with a silky texture - great for throwing over a singlet on a cool evening. A crisp cotton mens shirt would work equally well.
3 x bikinis, 1 x swimsuit
I’ve been friends with the brand Lido since the pandemic, when I pitched them this silly video during lockdown. I’d met the founder Daria in London a few years earlier - she’s Polish but based in Venice. Lido’s swimwear is fun, elegant, and lasts for years. She kindly gifted me a few bits for my holiday (but I’d buy them even if she hadn’t).
My favourite was the Trentasei Gradient in Midnight, which easily doubles as a bodysuit. It matched the stunning sunsets, and my mood. I also got the Venti Gradient in Negroni (such a good shade name) and a classic Venti triangle in black. The difference with their triangle bikinis is that you can wear them as halter neck per usual, or have the straps running parallel like a traditional bra shape.
Lastly I got the Undici Low Waist bikini for a more sporty style. Here are some dorky shots of me looking self-conscious about the prospect of putting swimwear pics in my newsletter:
1 x waist chain
Nobody makes jewellery like Santangelo! This waist chain is called Glory’s Forever. An easy and elegant way to accessorise your swimwear.
2 x t-shirts
1 white t-shirt, I chose this Cocteau Twins one that I bought on Depop. (I was fooled into thinking it was a cool vintage tee, but turned out to be a cheesy brand new replica - I’ve been in the process of re-weathering it ever since).
Then my beloved giant purple tee which I accidentally took two quite arty close-up photos of without really knowing how. Sometimes it pays to be a dweeby Milliennial!
2 x pairs of cycling shorts, 1 x pair of baggy adidas basketball shorts
Cycling shorts + a large t-shirt = easy 90s Lady-Di-on-holiday effect. Also cool with a bikini top for a beach lunch. Baggy basketball shorts for a sk8r boi alternative.
1 x Spiral Boxer Skirt
My fave from Dauan Jacari, made from deconstructed boxer shorts. You can listen to them talking about it on the podcast!
3 x tank tops
I buy my tank tops in multipacks from Hanes - I just get the largest size I can find in the kids ones.
2 x sun hats (one wide brimmed and one cap)
I guess I am also a smattering of no.2, because I bought this hat in Palermo last year. I think the rule of holiday merch is that it only becomes charming once you leave the place where you bought it.
3 x pairs of shoes
Flip flops, trainers for walks/hikes, and of course, my toe shoes!
What about you? Which genre of holiday dresser are you? Any packing hacks we should know?
Don’t forget to catch up on the Threads of Conversation podcast! Last week’s guest was Jessica Willis, Fashion Director at The Cut and frequent Kendrick Lamar collaborator (she worked on his Super Bowl Halftime show last year - the most watched in history).
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This is such a good guide G. I'm saving it for my next trip. Need to graduate from a (lazy) 3, to a 2!