The Cutest Transseasonal Dresses For Every Occasion

Set your pins free!

If you quizzed my legs during winter, they’d tell you that they love being ensconced in swathes of denim. But now that the weather is warming up and the watermelon slices are free-flowing, all they yearn for is to be set freeeeeee! 

This leaves me with four options when getting dressed: throw on a skirt, slide into some shorts, embrace my feminine side with a dress, or eschew pants entirely. Historically speaking, I’m not overly into skirts or shorts (or skorts, for the record) and wearing nothing but my undies in public will likely land me in jail, or worse, as the lead star in a stranger’s Instagram story. That leaves just one option, dear reader, and that is: dresses galore!

While I self-identify as a pants person more than I do a regular wearer of dresses, I’ve noticed that my shopping carts/saved Instagram pics have been singing a different tune of late. And might I say, I am digging the sound. I can’t be blamed for this ‘tude shift, really, since the internet is teaming with cutie patootie dresses that fit every type of social brief, from a picnic lunch with the in-laws to spritzes with a group of strangers that you just met at a bar.

Since you all have places to be, and important people to see, I’ve whittled down all the best dresses for every occasion into one delicious list for you to sink your teeth into below… Omnomnom…

The “Beach” Dress


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For what else is there to wear, during the #lastdaysofsummer, but gusset-skimming crochet

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After years of being half-committed to the cause, my main goal this Aussie summer is to be the kind of person who excels at going to the beach. Reach for the moon! Land in the sand! I’m talking pre-prepared snacks, ice-cold water bottles straight outta the fridge, a book in hand, and an crisp alcoholic beverage in the other (plucked straight from my mini esky, of course). With coconut-scented sunblock covering every inch of my body, I will watch the waves roll in from underneath the safety of my beach umbrella, and my own palpable smugness at being so organised (in tandem with Dolly Alderton’s Love Stories podcast) will be there to keep me company.

I will also be wearing one of the finest beach dresses this side of Sicily, listed from $$$ to $ for you below…

Splurge: Beach dresses should be easy like Sunday morning (save the ones where a spritz-based hangover is threatening to set fire to your organs/life). Think cottons, linens and a neutral colour palette. Okay, with house rules out of the way, let’s deep dive in to our favourites at the moment: this Faithful The Brand smocked linen dress is so cute I could *die*, and the same could/should be said for this Zimmermann crochet dress, this Reformation ribbed Margie dress and this She Made Me crochet number. If you’re looking to really dazzle your fellow sand-dwellers, then throw caution and the aforementioned neutral colour palette rule to the sea breeze, and treat yo’ bod to this Double Rainbouu number.

Save: PSA, YOU GUYS: This delightfully crisp white Bec + Bridge cotton wrap dress is currently half-price, and this black Moon River button-front dress isn’t far behind at the discounted sum of $100 (Australian) dollarydoos. Typing that sentence made me feel like I was starring in a Lowes ad, but no amount of shame will deter me from hunting down a bargain for you guys.

Wear with: These incred Ancient Greek Sandals.

The “Picnic” Dress 


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Summer swooshing by Fanny & Ganni 🐙⛱

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I’m applying the same expectations on myself with picnics as I am the beach this year. It’s officially the year of sunshine, snacks and sitting around with my best pals talking smack. It’s also the year of delightful picnic-friendly dresses, as you are about to find out firsthand with a smorgasbord of smocks that’d put any cheeseboard to shame.

Splurge: At the risk of taking the picnic theme too literally, I want to wear this GANNI ruffled check dress every second day for the rest of my life, alternating shifts with this Reformation floral slip dress. I’d also happily pop a cheese and cracker in my mouth whilst wearing this Reformation midi-dress., or pour myself a life-affirming mimosa in this S-T-U-N-N-I-N-G Rejina Pyo checked cotton dress.

Save: If you’d rather spend all your dosh on gourmet deli items, DW you can still look like a total snack in the following gawjuz dresses: this gingham smock dress from The Iconic, or this green floral MVN midi-length dress,

Wear with: A picnic rug, of course! (Oh, and this glorious Clyde straw hat).

The “Going Out” Dress


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😈 AS IF 😈 Dreamgirl @devonleecarlson wearing her Christy dress in Palm Springs

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Despite the fact that it’s becoming increasingly less age-appropriate for me to do so, I find no greater pleasure in life than getting ready for a night out with my gal pals, blasting R&B through the speakers, popping a bottle of champers and spending far longer than necessary getting ready together to hit the town (or probably more accurately these days, going out for a ~nice dinner~). This pre-game event always surpasses the actual event IMHO, especially when you have a sass-heavy new dress to take for a spin. Like these bonafide party starters:

Splurge: This Cara Dress from Reformation could realistically span all categories, depending on whether you pare it back with a pair of flip-flops or turn the heat up with a strappy French girl heel, but I daresay it’ll feel most comfortable in the company of a dirty martini. If you’re feeling a bit ~wild~ then this Daisy leopard print mini dress was literally/figuratively/metaphorically/spiritually made for you, and I’m making it my mission to drop it like it’s haute in this 90s supermodel-inspired Realisation Par dress come summer, too.

Save: If you’re sold on the animal print trend, but don’t want to spend the lion’s share of your pay on a dress, then this ASOS animal print skater dress has got chu. Or, really make heads turn on the DF with this H-O-T pink slip dress from The Iconic.

Wear with: This Fenty Beauty highlighter and your sassiest mood.

The “WTF Is The Weather Doing” Dress


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Autumn anyone ? 🍂🐣

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Don’t get it twisted: the in-between months are my all-time favourite, but gosh damn the weather can make it hard to get dressed of a morning. One minute it’s all sunshine and lollipops (/crippling humidity), and the next the sky is opening up to expel several million litres of mood-dampening rain onto my day. Despite the fact that I check my weather app upwards of eleven times a day during this time, I never feel sartorially prepared. As I’ve recently found, though, circumventing these plot twists is as easy as investing in the right dress. Evidence below:

Splurge: This polka dot Kate Sylvester dress (pictured in the lead) is so swoon-worthy I almost lost my balance when I first looked at it—lightweight enough that you can wear it on a hot summer’s day with sandals, but also approachable enough that you can pare it back with sneakers and a jumper. Samesies with this Kowtow peach cord dress that has the added bonus of looking super kawaii over a pair of trousers.

Save: This super cute ASOS button-up body con dress would be as equally at home paired with sneakers and a jacket as it would with a pair of leather slides, making it the perfect option for those ‘da fudge you doing weather?’ days. The same could be said for this cute as a bloody button ASOS puff-sleeve dress which I bought within seconds of peeping it on their site.

Wear with: Depending on what’s up with the sky, a pair of Veja sneakers or these heavenly Maria Farro leather flip-flops.

Words, Madeleine Woon