10 Epic Summer Holiday Outfits I Wish I'd Worn First

My summer holiday for the season is a distant memory. I came back two weeks ago from Spain, but it feels an eternity since I was hitting the beach, eating all the tapas and generally living my best life in some of my best clothes. Do you also save some of your favourite outfits for getting away? If so, this gallery is for you.

I've been vicariously extending my summertime sojourn through all of the many girls I follow on Instagram, who appear to be on a permanent vacay. There's Callie in Montauk, Monikh in Mallorca, Emma in Los Angeles, Tiffany in Puglia, and many, many more who I'm not only stalking for restaurant recommendations, private-beach tip-offs and local shopping destinations, but for their impeccable holiday outfits too.

From the way to accessorise the simplest of swimsuits to the fancy formulas you can take from your suitcase and translate well back into city life, these are my favourite holiday outfits worth copying…


Satin Evening Dress + White Sandals
(Image credit: @monikh)

Style Notes: Monikh's slinky evening look has been on my mind for weeks. I think it's the vibrant burnt orange set against white sandals and a hippy beaded bag. So simple but so effective.


White Smock Dress + Hat + Slides
(Image credit: @kouthwiel)

Style Notes: Kouth's simple smock dress is a great base for piling on extroverted accessories like her striped sunhat.


Knotted Bandeau + Matching Trousers
(Image credit: @katrinarazon)

Style Notes: This kind of matching set has been taking over Instagram, and Katrina's wearing hers in just the right way: with a smattering of gold jewellery.


Printed Slip + Boho Bag
(Image credit: @calliethorpe)

Style Notes: Every now and then, we are reminded that the simplest outfits are the best outfits. Thank you, Callie, for giving us this reminder of a printed slip and macramé bag.


Knotted Shirt + Slip Skirt + Slides
(Image credit: @leiasfez)

Style Notes: Leia gets extra wear out of everyone's favourite slip skirt with a knotted shirt, slides and a '90s-style bag. All kinds of chic.


Hawaiian Shirt + Shorts + Heels
(Image credit: @emmanuellek_)

Style Notes: Emmanuelle's mad mashup has me so intrigued. The juxtaposition of the "dad" shirt with sassy heels is very, very clever.

Related: The 5 Sandal Trends You'll Spot in Every Street Style Gallery This Summer


Cami + Comfy Pants + Party Heels
(Image credit: @emmahoareau)

Style Notes: Emma's aesthetic is all about the pinky tones, and this combination of a dreamy camisole, slouchy trousers and PVC sandals really plays into it. Sunset cocktails, here I come!


Polka-Dot Co-Ords + Sneakers
(Image credit: @itsmekellieb)

Style Notes: Kellie's double-dot extravaganza is just the ticket for sightseeing—especially with a pair of comfy sneaks.


White Swimsuit + Bucket Hat + Beaded Bag
(Image credit: @lucywilliams02)

Style Notes: Not strictly an outfit you could wear to, say, dinner, but Lucy's well-accessorised swimsuit is very ready for a stylish beach or pool.


1950s Dress + Mini Bag + Heels
(Image credit: @handinfire)

Style Notes: Tiffany looks like she's stepped out from a '50s movie in this incredible dress. Square-toed mules and a mini bag keep it up-to-date, though.

Hannah Almassi
Editor in Chief

Hannah Almassi is the editor in chief of Who What Wear UK. Hannah has been part of the the Who What Wear brand since 2015, when she was hired to launch a UK sister site and social channels, localise content strategy and build out the editorial team. She joined following a seven-year tenure at Grazia magazine, where she led front-of-book news, fashion features and shopping specials as fashion news and features editor. With experience in both print and digital across fashion and beauty, Hannah has over 15 years in the field as a journalist, editor, content strategist and brand consultant. Hannah has interviewed industry heavyweights such as designers including Marc Jacobs and Jonathan Anderson through to arbiters of taste including Katie Grand and Anna Dello Russo. A skilled moderator and lecturer specialising in the shift to digital media and e-commerce, Hannah’s opinion and work has been sought by the likes of CNBC, BBC, The Sunday Times Style, The Times and MatchesFashion.com, among many others.

Hannah currently resides in Eastbourne with her photographer husband, incredibly busy toddler and highly Instagrammable cat.