Everything I Wore in the Carribean, Evening edition

Holiday dinner outfits for some pre-summer inspo

I’m always inspired by where I’m going on holiday for what to pack and for the mood and how I want to feel throughout the week. For our recent trip to Antigua I was feeling a pull towards preppy, low-key looks that felt a little 80s at their core. The kind of looks Elisabeth Shue might have worn in the 1988 movie Cocktail or Cameron Diaz in Head Above Water. By day this is easy enough; relaxed crisp cotton shirts, sporty shorts, simple swimwear, caps and stripes (that’s the next Substack). By night, I think my penchant for 80s/90s preppy Club Tropicana branched more into some kind of beach house chic by way of Carrie Bradshaw and Laura Harrier, two muses who speak to different parts of my sartorial soul. A bit playful, a bit refined and these looks *I think* fall somewhere amidst all that swirling around my brain.

As you’ll see I basically wear the same bag every single night and rotate between 2-3 pairs of shoes. I actually packed way more than this so this was a great lesson. In the winter I’m all about accessories and coats and keep everything else pretty much the same (jeans and knit) but when I’m in summer-mode I really get my kicks from clothes and outfits and just rotate the same accessories over and over. It’s interesting to see how this plays out in real time here and makes me realise how hard some of my accessories work!

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I was excited for this cute little puffball skirt to finally get an outing. Everything Kiwi designer Maggie Marilyn turns her hand to I just love. I’d love to bottle whatever the formula she has for creating pieces that are both cool and playful but not rooted in trends or ‘cult’ status so they stay beloved no matter how many wears. I wanted to keep it casual but also grown-up hence the crisp, collared shirt and flip flops juxtaposition; a beach bum with a job if you will. The big flower earrings are just a nice whimsy to top it all off.

Shirt - here | Skirt - Maggie Marilyn | Shoes - J.Crew | Bag - Jil Sander (this does something similar) | Earrings - Completed Works x TOVE | Cuff - Tiffany