What To Wear On Holiday

Creating a moodboard of summer looks I love helps set the tone and makes packing way easier. From there, I think realistically about where I’m going, what I’ll be doing, and how I want to feel. Just like at home, my holiday style should feel easy and uncomplicated – no overthinking, just outfits that work.

The Packing Process

I pack a curated case where everything works together. A slip skirt that goes from beach to dinner, a linen set for exploring or sundowners. Rewearing pieces in new ways keeps things interesting without overpacking.

Before I pack, I think about what I already own and love. What fits the moodboard? A slip dress I’d wear with a blazer to a meeting suddenly works beachside with flip-flops and slicked-back hair. No need to buy a whole new wardrobe.

I like limited options – it makes getting dressed easy. I want outfits that feel good and work for whatever the day brings.

Shoes are where I keep it really tight. One sturdy slip-on, maybe a trainer, and that’s it. If something already serves a purpose, I don’t pack another version just to match.

Always check the weather, especially evenings—lesson learned after too many packing mistakes.

Packing cubes (I love Antler) keep me organised, and I bring hanging pieces on hangers in a garment bag. Easy to unpack, no need to call for extra hangers.

Leave the ‘this will do’ pieces at home. I’d rather have fewer things I love than a suitcase full of maybes.

The Airport Outfit

The holiday begins the moment I step into the airport, so I always plan my travel outfit. Nothing too fancy – just something I’ll feel comfortable and cool in.

A blazer that can double as a cover-up for the evening or an oversized shirt that works for the beach. I want to look pulled together and relaxed, never scruffy. Comfortable footwear and layers are key for long journeys.

I keep it simple with a relaxed trouser, tank top, and layer with a shirt and blazer. Always a light knit or sweatshirt – planes are cold! Cosy socks and Birkenstock Bostons or Trainers for comfort.

An oversized tote, like my Suede Liffner Bag, is essential, plus smaller bags (I love Space NK Travel Bags) to keep my essentials organised.

The Airport Approved Edit

1. Matching Pyjama Style Sets from Yaitte make for excellent travel outfits. The Striped Shirts + Boxer Shorts are great for beach cover-ups, too
2. Donni is another brand I turn to for easy travelling pieces. Especially the Striped Pants +  Sweats. In fact, I could wear Donni all holiday. The Boxer, The Striped Shirts, The Silk Pants and Taffeta pieces would all make for a stylish holiday wardrobe
3. 4th & Reckless has a great selection of sweats, perfect for travelling at affordable prices

What To Wear For… Travelling

A Graphic Tee, Comfortable Trousers + a Blazer (a sweatshirt will also be in my oversized The Row Tote). An Antler Carry-On and a Baseball Cap. Understated, practical and pulled-together.

Adidas Track Pants, Skims Tee and an Oversized Shirt. Cashmere Socks and Suede Slingback Flats. Comfortable and Chic thanks to the muted colour palette.

I rarely travel in jeans, but if you like to, these ones from Frame are super soft. I love the red accessories with this look for a pop of interest.

The Beach Mood

I try to stick to a colour palette, usually monochrome with a splash of colour, and incorporate my everyday wardrobe into my holiday style where possible. An Oversized Shirt, a Graphic Tee, a Striped Short Set, and a Lace Slip Skirt all work well as beach or pool cover-ups, and make me feel like I’m not straying too far from my usual style.

For lazy days spent by the pool or on the beach, I want comfortable swimwear and easy-to-throw-on cover-ups. I don’t want to take on a whole new style personality when I’m on holiday, but it’s nice to pack a few special pieces. I’ve just ordered this dress from Loretta Caponi to live out my best White Lotus life, and I wore a Pippa Holt Kaftan to lunch at Hotel Splendido in Portofino during my last holiday and felt very fancy.

Hunza G is my go-to swimwear; I find them so comfortable. I go for Bandeau Styles to avoid the dreaded tan lines. I’ve had more interesting swimwear in the past, but I just want something simple and easy to wear. Toteme also do a Shirred Stretch Fabric Swimsuit that I want to try.

An oversized sarong is a must; I love this Monogrammed Toteme one. Pair with a swimsuit and an oversized shirt.

I always opt for a simple flip-flop. Ancient Greek Saionara Leather Sandals are low-key and perfect to team with beachwear.

A Striped Co-ord Set is something I usually pack for sundowners. Slipping on something cool and cosy after a day at the beach is heaven.

Linen pieces and sets are something that always make it into my case. They’re great for sightseeing, I lived in this H&M Pyjama Set on a recent holiday, and this Free People Co-Ord.  Mint Velvet also has some great linen pieces, and Deiji Studios’ Sets are a must-have for holiday outfits.

Faithfull and Posse are brands I turn to when looking for those elevated everyday summer staples. Pieces I’ve had in my wardrobe for years and never fail to make me feel amazing when I pack them for a trip. I’ve had my Posse Tailored Linen Shorts for around 8 years.

For a beach bag, it’s usually my Dragon Diffusion. A good size, easy to throw all my essentials in, and they go with everything. Check out Anthropologie’s version of a similar woven leather style. I also love this oversized Cos Tote.

The Beach Approved Edit

1. Ancient Greek Sandals for simple yet stylish Flip-Flops + Sandals
2. Hunza G for comfortable + cool swimwear in a number of colours and styles
3. Deiji Studios for timeless linen sets you’ll pack year after year
4. Posse, for those easy-to-wear yet elevated everyday holiday pieces (available at NETAPORTER)
5. Faithfull, stylish summer separates and dresses with a nod to vintage patterns and designs (NETAPORTER + Harvey Nichols)

What To Wear For… The Beach

Packing my Satin Slip Skirt + a Graphic Tee for an easy yet cool look. And sticking to my monochrome theme.

A simple, chic and practical look for a day in the sun. From breakfast to a quick cover-up to sundowners. An Oversized Shirt, a Sarong and Jelly Flip-Flops are my beach essentials.

A Crochet Set for lunch, something a little fancier than my usual beach style. This one is from Anna Kosturova– they have some really fun beachwear. And I love this Oversized Hand-Woven Tote from Cos.

The Evening Mood

I really lean into simple pieces in beautiful fabrics and warm colours for the evening while on holiday. I very rarely pack heels or blow-dry my hair when I’m away. A slicked-back bun, minimal makeup, and a simple slip dress is my go-to look, paired with flip-flops and jewellery to elevate.

Slip Dresses are a must. These Satin Slip Dresses in Brown and Neutral are great if you prefer to wear a bra, thanks to the thicker straps.

Interesting accessories like these Fringe Bags from Françoise or Tassel Earrings from Jennifer Behr keep my simple look elevated in an understated way.

This Satin two-piece from LESET is exactly how I want to dress for evening on holiday. The Wide-Leg Pants would also work with a simple tank or bandeau top.

Brands like Rat & Boa, Sir and Dissh design pieces perfect for warm holiday evenings.

The Evening Approved Edit

1. Mint Velvet Slip Dresses, for a simple evening look
2. Asceno Silk Pieces, Dresses, Sets or Pyjamas all make for chic and comfy evening attire
3. Dissh, for elevated pieces that work just as well for a summer in the city as they do on holiday

What To Wear For… Evening

A simple Floral Silk Dress from Sir with Leather Flip-Flops from A. Emery.

A Scarf-Detail Draped Dress with gold accessories and a sandal with a little more detail from A.EMERY.

I love a matching set on holiday. This LESET one is perfect for a chilled evening look. The Fringed Bag adds interest in an understated way.