Anna Cascarina, a fashion editor, stylist, and content creator, has likely caught your eye on social media with her distinctive yet timeless style. Now an author, we had the opportunity to capture her at home in some of her favourite Whistles pieces before launching her book, ‘The Forever Wardrobe.’ We delved into topics such as approaching ageless style, writing her new book, and challenging conventional fashion norms.

With the rise of social media, there’s less experimentation; many people follow the same trends, which is a shame because fashion is the perfect way to express personality.

You mentioned working closely with an illustrator on this project. Can you tell us more about the illustrations in the book and how that process worked?
She was amazing. Her name was Ludivine Josephine, and she’s based in Florida. We worked closely together to create timeless illustrations that were also fun and inspiring, so there was a lot to balance and get right. I also wanted to ensure that the illustrations were as diverse as possible and included disabilities. It’s really important to me, and Ludivine was amazing at doing that. I wanted to make sure everyone could relate to them.

Every project comes with its own set of hurdles… Could you highlight any unique challenges you encountered while writing ‘The Forever Wardrobe’ and how you overcame them?
Initially, I was worried about the timeframe, as I was given two months to complete the book. However, I enjoyed the process once I started, and the deadline motivated me. A significant challenge was condensing the word count, but the team at Bloomsbury was fantastic in keeping me on track, and my editor was terrific. Working with an illustrator was another new challenge. It isn’t easy to convey an image you have in your head to someone else, but she was incredible, and it all came together beautifully in the end.

I prefer minimal aesthetics now. However, it’s important to me to still add personality. I achieve this with an interesting silhouette or accessories that bring a sense of individuality. It’s important to do this so we don’t all look the same.

What advice would you give those looking to make similar changes and build a forever wardrobe?
If you start to find your style and know what you love, then you can start to cut out all of the noise. Instead of buying every trend you see or trying to replicate someone else’s style, you’ll know what’s for you and what you need in your wardrobe.

What’s your favourite piece of clothing or accessory that you own, and what makes it special to you?
My Chanel classic flap bag was a surprise gift from my husband for my 40th birthday—he got the exact one I would have chosen myself. I actually cried when I opened it. It’s completely timeless, and I love it so much. It’s pristine, as I’ve looked after it so well.

How do you approach styling for different seasons?
I have a selection of pieces I wear throughout the year, such as cashmere sweaters. Then, I have my core pieces for each season. In winter, I’m more minimal, and I like structured things. I’m more experimental with colour in the warmer months. I like to add brights and prints alongside earthy colours like brown and khaki in the spring-summer. I opt for more flowy 70s shapes in the summer, too.

…and occasions?
Many people struggle with this, and we don’t want to spend loads on things we will only wear once or twice. However, I have some beautiful dresses I’ve owned for years, which I bring out each summer for occasions like weddings. I suggest renting more often, as it’s a fantastic way to wear something special without buying a whole new wardrobe. There are also many rental places with sustainable practices and dry cleaning, so it’s worth looking into.

If you could raid the wardrobe of any fictional character, be that from a book, film or TV show, whose wardrobe would you choose?
Growing up, I adored Pretty in Pink, so Andy is one of my top picks. Breakfast at Tiffany’s is also a favourite, and Holly Golightly’s style, by Audrey Hepburn, is iconic. I also admire Michelle Pfeiffer’s character in Scarface and, of course, Carrie Bradshaw.

And if you could travel in time to any fashion era, which would you choose?
The 70s because I’m a child of the seventies. I love that retro aesthetic: prints, fringing suede and leather. I’d also love to delve into the 20s and the era of flapper dresses. It was an exciting time for women. After being corseted and more restrained, they had a new sense of freedom.

What’s one fashion rule you believe should be broken more often?
I address age and ageism in fashion a lot, and it bothers me when people feel restricted from wearing certain things based on age. Everyone, regardless of age, gender, size, or ethnicity, should feel free to experiment and wear what brings them joy. As we age, societal expectations around wardrobe change, and it’s frustrating. I want us to break free from those constraints and wear whatever we want.

As we age, societal expectations around wardrobe change, and it’s frustrating. I want us to break free from those constraints and wear whatever we want.