Tash Oakley’s Holiday Rules

How has travelling inspired your fashion? Travelling has always kept my “creative juices” flowing which has inspired a lot of my fashion taste and style. I like to be immersed in the city I’m in, learning the culture, language, people, and of course, pay attention the fashion trends.

When and how did you decide you wanted to go in the swimwear apparel direction? Moving in the swimwear apparel direction was the natural next step after Devin and I started ABikiniADay. We noticed how desperately the swimwear industry needed a swimwear line targeted towards fit, and comfort instead of seasonal trends, and we knew we had enough knowledge of the industry and passion to see this through.

What inspired you to launch Monday Swimwear? Monday Swimwear was inspired by a need Devin and I saw in the swimwear apparel industry. Devin and I were born in beach towns and spent the majority of our free time on the beach in swimwear. We loved the beach, it was and still is our happy place, and we were excited to create swimwear that had it all- support, comfort and a timeless and on-trend style.

How do you get inspiration when designing your swimwear line? We pull a lot of our inspiration from our travels, and the women we meet! We are always at pulse with what our customers are saying and wanting and always create with them in mind! We like to add pieces to the range that are classic, timeless, and versatile.

What is the best career advice you have been given? Some of the best advice I’ve been given was to do what I love so I won’t ever have to work a day in my life. Running your business requires full-time attention- you don’t get to clock out and forget about the day and it takes a toll on you mentally and personally. Pursuing what you love definitely bridges the gap and makes it all worth it!

What accomplishment are you most proud of? Launching Monday Swimwear is definitely my most proud accomplishment. Devin and I worked so hard in the lead up to the launch and still work hard in every stage of growing our business!

How do you stay focused on accomplishing your goals? Maintaining a healthy lifestyle has helped me stay grounded, focused, and centred, giving me a clear mind to see through my goals. I also have an amazing and very positive team that is very supportive and hard working. It takes a village to raise a business!

What is your favourite workout to do while on vacation? I love doing workouts on the Peaches Pilates app, incorporate workouts from my pilates classes, and take advantage of the scenery around me!

What do you make time to do for yourself every day? Every day I like to spend 20 to 30 minutes doing some sort of self-care- taking a warm bath, having a glass of wine, going on a walk, reflecting, or listening to some music.

What is your favourite vacation destination? 

Definitely Italy! I’ve been spending my summer’s in Italy for the last few years, and it’s one of the trips I look forward to most all year! Italy is a perfect combination of everything I love- beautiful beaches, amazing food, hospitable and kind people, and the best shopping! Everything about Italy tends to symbolize vacation for me! My favourite part of Italy is Capri, Positano and the Amalfi Coast! When I have time, I also like to visit some of my other favourite cities like Lake Como, Florence, or Venice- Italy has so much beauty to offer!

Where is your favourite island hotel? 

It’s so hard to decide because every island I visit has its own beauty but St Barth’s has always had my heart! St Barth’s has the cutest beaches with gorgeous sunsets, and the French tradition is immersed in the island’s food and culture.

What destination is on your bucket list? 

I’ve been so fortunate to already have visited so many beach destinations and cities from my bucket list but the Maldives is definitely one that I would love to experience soon. I’ve yet to see one bad photo of the Maldives- it looks picture perfect and I’ve only heard amazing things about the island!

What is your favourite spa? 

Wow, not sure if I can choose just one since so many properties I stay at have such amazing spa facilities, but the Rosewood or Belmond properties stand out to me!

What is your vacation style? 

It’s really to hard say because most of my travels incorporate an element of work even though it never really feels like work. Even when I am on Holiday, I still like to check in with my team and have Monday Swimwear at the top of my mind. I also pull a lot of my inspiration from my travels- from the hues I see, culture of the city, and the amazing women I meet. My days are usually based off some light work and e-mails in the morning, then I like to spend a portion of my day in the sun and water enjoying the moment. I’ve learned how to check out and be present which helps me transition from work to pleasure on vacation. I also love to try delicious local food when I travel and visit local shops. Aside from planning dinners, beach clubs or anything else that requires a reservation, I’m flexible to go with the flow of the city and the energy of the trip!

How do you get ready for a beach holiday? 

I think at this point I’ve mastered preparing for a beach holiday! Aside from planning, booking and organizing the logistics, I love to do some shopping to prepare for my holiday. My favourite shopping is usually for accessories, hats, and seasonal beach bags. I usually have some looks I’m excited to wear and share on the trip. When I find a favourite beach destination, I usually become a repeat traveller there so I always have my favourite restaurants, and activities pre-booked for the trip! It always gets me looking forward to being back in that space and energy.

How do you stay in shape on a holiday? 

Strangely I enjoy working out on Holidays! It helps me maintain my structure and feel good! I also feel a little less guilty eating the bowl of pasta or splurging on dessert!! I like to stay at resorts or hotels that have a gym on the property and do my workouts first thing in the morning before breakfast. It helps me feel accomplished and energized before 10 am!

What do you pack to exercise on a vacation? 

I like to pack tons of the basics- lots of leggings, a pair of my favourite workout shoes, and tons of sports bras! If there isn’t a gym on the property, I’ll usually try doing an online workout routine like PVolve or Body by Gilles.

What are your 5 packing essentials? 

1. A large beach bag so you can put all your beach/pool necessities, I love the Monday Swimwear Lake Como bag. It is big enough to keep all my SPF, towels, phone chargers, etc.
2. An oversized beach hat to protect your face and hair from the sun. I pack the Monday Bondi Beach Straw Hat because it is flexible and can be packed in my suitcase but maintain its shape.
3. Monday Beachwear- it’s so versatile and can be worn from the beach during the day to night so you don’t need to overpack too many looks. I love the sarongs and beach sets. The sarong can be worn in so many different ways like a skirt, top, and dress! The Tahiti beach pants are also really light, airy and versatile! I can dress them up or down which is really nice!
4. SPF! Coola and La Mer are my favourites.
5. A book!

Do you have any packing advice? 

I would suggest pre-planning looks and trying everything on before packing! I start shopping and thinking about my outfits weeks in advance in case I need to return anything or exchange sizes! If you have any special activities or dinners planned, having a prepared look always gets you more excited. I also love infusing the culture of the city into my outfits to get me inspired and excited for the trip! I roll all my clothes tightly for more space in my bag!  In regards to handy gadgets I travel with, don’t forget converters, travel steamers, and chargers!

How do you take care of your skin when you’re travelling? 

Hydrate!! I like to use an extra moisturizer before travelling on the plane and hydrate using a mist and serum on the flight. A lot of people don’t correlate the two, but drinking lots of water is essential for your skin to feel and stay hydrated. I cannot travel without my water bottle on hand!  I also like to pack some of my favourite face masks and use them throughout the trip depending if my skin is affected by the altitude, climate change, or air pollution.

What is your airport style? 

Casual and comfortable. I’m usually always sporting a tracksuit and sneakers! It can get stressful travelling and being on a plane for hours so I like to stay as comfortable as possible.

Do you have any beauty tips for flying? 

I like to use my Summer Fridays Jet Lag mask for long flights to keep my skin hydrated. If you apply a little at the beginning of the flight, it acts as a moisturizer and my skin usually absorbs it pretty fast, and I quickly notice a difference! I’m also a huge fan of Caudalie’s Beauty Elixir. It’s a really nice and light mist that keeps your skin feeling hydrated. I usually like to apply it every couple hours on a flight depending on how dry my skin feels.

What swimwear trend is a must this season? 

This summer I am loving high cut legs and high waisted bottoms. They are so cute and really flattering for so many body types. Also, the balconette style and underwire tops have really taken off!

What activewear are you loving? 

I have such simple activewear style I usually stick to all black and anything stretchy and comfortable in the gym, but lately, I’ve been loving playing with some colours like dark greens and light pinks!

-Photographed by Emily Abay in Monday Swimwear