Occasionally with, Tash Oakley
This months Occasionally guest is none other than Tash Oakley. Tash's energy is contagious and her creative mind shines through her style with ease. Explore her special occasion do's and don't's below
Tash Oakley is an Australian entrepreneur, influencer, and co-founder of Monday Swimwear. She splits her time between Australia and Los Angeles, and between business and beach days. She embodies such effortlessness and carefreeness, not just in the form of summer content but in everything she does. Here, we deep dive into some of her favourite moments, how she preps for special occasions and - more specially - what impeccably elegant outfits she’s sporting when she’s not in a bikini.
Take us back to one of your favourite occasions. Why is it a favourite and what were you wearing?
It has to be my wedding. It was a five-day celebration, and I truly loved every single outfit I wore—but the one that stands out most was my look for the welcome drinks. I wore a custom J’Aton Couture gown, designed in collaboration with my dear friend and stylist, Marina Didovich. The dress was daring yet elegant, and it captured my style and the energy of the night so perfectly.
That evening, we welcomed our dearest family and friends to Capri to officially kick off the celebrations. We hosted the welcome drinks at Gran Caffè in the piazzetta, and the atmosphere was electric—it spilled into the square as we danced the night away. A local scialapopolo band played, adding so much joy and authenticity to the night. Truly one of my favourite memories, made even more special by one of my favourite dresses.
What was your most recent occasion and what did you wear?
I just returned from St. Barths, where we shot the Monday Swimwear Summer ’25 campaign. We have so many exciting pieces coming, but I’m especially obsessed with the new Levanzo wrap dress. It’s a classic silhouette that transitions so effortlessly from day to night—I already know it’ll be one of my staples this summer.
What’s one occasion you wish you could go back and re-do, and would you dress differently?
I try not to have regrets, but if I could go back, I’d revisit one of my earlier red carpet events. I’d love to re-style the look with the confidence and more of a refined eye I’ve developed over the years. It’s amazing how much your personal style evolves!
What would you wear for:-
Your own birthday event
A simple, timeless dress paired with meaningful jewellery. Last year, I wore the Jennifer Cupro dress in ivory from Misha (such a stunning design!) and styled it with my beautiful Bvlgari pieces. It felt effortless but elevated—just how I love to feel on my birthday.
A best friend’s birthday party
A killer LBD. Miaou makes some beautiful options, and I’ve also been loving what Meshki has been releasing lately.
A dinner with friends
You can’t go wrong with jeans and a cute top. My go-to jeans are from Moussy Vintage—they’re the most comfortable and flattering ones I own.
A summer wedding
It depends on the location, but something long, flowy, and colourful always works. I once wore a green Retrofête dress to a friend’s wedding in Lake Como and loved it. Aje and Michael Lo Sordo are also great for this.
A winter wedding
I love a long-sleeve maxi in a fun colour. I recently wore a stunning open-back green gown by Victoria Beckham that felt perfect—chic, elegant, and a little unexpected.
A black tie event
I love a statement gown. Right now, I’m obsessed with sequin maxis—they feel glamorous and fun.
A summer garden party
A long, flowy skirt paired with a crisp white shirt—or a breezy maxi dress. Light, effortless, and elevated.
In general, what are some of your favourite brands for occasion wear?
Magda Butrym, Retrofête, Galvan London, and The New Arrivals are my top picks. For more budget-friendly pieces, Misha has some incredible finds, too.
Favourite dresses or pieces you own?
One of my forever favourites is the Montego Maxi Dress from Monday Swimwear. It’s one of those pieces that makes a statement every time it’s released in a new colourway—flattering, comfortable, and endlessly versatile.
And what’s your most cherished piece of clothing or accessory?
Hands down, the Monday Swimwear Hamilton pants and sweater set. I live in them. They’re some of those pieces I couldn’t imagine my wardrobe without.
Let’s get into accessories. What are your favourite pieces and which brands do you go to for jewellery, bags or shoes when you have an event or occasion coming up?
For jewellery, my Bvlgari Serpenti pieces are my everything. Being part of the Bvlgari family has been so special to me, and I wear these pieces daily. I usually go with white gold for occasions and gold for everyday wear.
For bags, my current favorites are between a silver mini Lady Dior (obsessed!), a gold Bottega Veneta Knot clutch, and a classic black mini embellished Chanel. I also love sourcing vintage clutches for special events.
When it comes to shoes, Gianvito Rossi is my forever go-to—they’re so comfortable and elegant. For more affordable options, I love Billini and Dolce Vita.
On your wishlist?
A vintage Patek Philippe watch had been on my wishlist forever, and Material Good recently sourced it for me. I’m so in love and so grateful!
What special occasions do you have coming up, and what looks are you planning?
There’s so much happening! We’re being honoured at Miami Swim Week this year, and we have a ton of exciting new Monday Swimwear pieces launching, so I’ll be living in the latest Monday’s pieces for most of the summer!
What’s your ultimate confidence-boost kind of outfit?
Any bikini from Monday Swimwear paired with a sarong and our La Jolla shirt. I feel my absolute best in it—and that’s one of our biggest selling points. The way Monday makes you feel is unmatched.
Which outfit or items always attract the most compliments?
A full Monday look, without a doubt!
What’s your favourite era for occasion wear? Do you have a most iconic fashion moment / style icon / red carpet look that inspires your formal wardrobe?
I’d say it’s a blend of '90s minimalism and 1930s Hollywood glamour. I love a timeless silhouette—subtle sexiness with low backs, plunging necklines, clean lines in silk or satin, and elegant draping. Glamorous yet understated.
Let’s move into beauty and, more specifically, make up, for special occasions. Do you have any favourite products or a go-to look you love to create for evening occasions, and how does it differ from your everyday make up?
I like to keep things natural day-to-day—just enhancing my features. For evening, I add a deeper bronze, a bit more colour on the eyes, and a stronger lip combo. I love Huda Beauty’s Lip Contour in Honey Beige for day and Warm Brown for night.
And how do you prep before a big occasion?
My prep starts with rest—beauty sleep is non-negotiable! I stay hydrated, do a morning Pilates session to ground myself, then an “everything shower” and hair treatment. I blow-dry and pin my hair, then do my makeup. In the lead-up, I do red light therapy 3–5 times a week and make sure I’m nourishing my body. It’s more about feeling my best than any specific aesthetic.
You're hosting at home - how would you dress, what would you serve, what’s on your playlist and who would you invite?
I’m imagining a summer evening at my Palm Beach home in Sydney. I’m in a flowy, comfortable dress—likely Monday Swimwear. Theo (my husband) and I cook a Mediterranean spread: Theo’s baked ocean trout with yogurt, tahini, and fresh herbs, side salads, and spanakopita. We play our “Capri Piazzetta” playlist that we made for our wedding and invite our closest friends.
Quick Fire Questions:
Staying in or going out?
Staying in.
Heels or flats?
Small heels.
Out late or home early?
Home early… mostly!
Colour, print, black or white?
Black and white.
Silk or embellished?
Tough choice—but silk.
A little early or a little late?
A little late… oops.
Planning ahead or dressing last minute?
I try to plan but usually end up dressing last minute as plans always change!
Vintage or new?
Both!
Bold statement or understated elegance?
Understated elegance.
Comfort first or style first?
Comfort = confidence.
Statement jewellery or subtle jewellery?
Lately, statement.
Fun and creative or classic and timeless?
Classic and timeless.
Finishing touch before leaving the house?
A spritz of Lys by Le Labo.
One thing you never leave home without for a special event?
A mirror selfie—always!
Some of Tash’s Favourites:
1. Gold clutch 2. Lip liner 3. Sweater 4. Pants 5. Perfume 6. Ivory dress 7. Black dress 8. White Shirt 9. Bikini top 10. Bikini bottom 11. Sarong 12. Green dress 13. Silver bag