I'm a 50-Year-Old Fashion Expert—5 Luxury Buys I Truly Think Are Worth Investing In

So, you've reached a point where you can afford to spend a little more on your wardrobe and start building up a collection of premium pieces. But where to begin? Not all luxury buys can justify their price tag, but recognising which items deserve your splurge is a skill that takes time to hone.

As a fashion editor, lecturer, stylist and author of The Forever Wardrobe, Anna Cascarina is well-versed in sifting through the hundreds of high-end brands competing for our attention and identifying worthwhile investments. With 25 years in the industry, Anna helps people maximise their wardrobes and refine their shopping habits, focusing on versatile items that stand the test of time. With this in mind, she's the perfect person to steer us through the overwhelming world of luxury fashion.

Below, Anna shares the five items she shops with a more generous budget. Experience has shown these pieces to be fundamental to her everyday style, making high-quality versions a smart investment. They're not just timeless to Anna, though—the following are widely relied-on staples, essential to most fashion enthusiasts' rotation. Scroll on to hear why she deems them worthy of her (and your) money.

1. Leather

Over 50 luxury shopping: @annacascarina wears a leather jacket from Tibi

(Image credit: @annacascarina)

“I love leather, but not all leather is created equal. Investing in buttery soft leather that's beautifully made will give you a lifelong friend that you'll return to again and again. I bought this Tibi brown leather bomber a few years ago and still adore it just as much as the first time I wore it. The shape is perfectly oversized and it fits like a dream.”

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2. Lingerie

Over 50 luxury shopping: @annacascarina

(Image credit: @annacascarina)

“Lingerie is always worth investing in. Making sure you buy the right size bra and well-fitting knickers is essential in creating the building blocks of your outfit. If you're wearing good lingerie, you'll always feel your best. This set is from Dora Larsen, one of my favourite brands along with Stripe & Stare which is my go-to for comfy underwear.”

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3. Handbags

Over 50 luxury shopping: @annacascarina

(Image credit: @annacascarina)

“In my opinion, the best thing to invest in is a great designer bag. I have been ‘collecting’ them for a while, but my all-time favourite is the Chanel bag my husband bought me for my 40th. It's a beauty and still in pristine condition. However, one tip is to think about how you want to wear your bag. I like to wear mine as a cross body but unfortunately, my Chanel strap isn't long enough, which does mean I don't use it as often as I'd like.”

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4. Knitwear

Over 50 luxury shopping: @annacascarina

(Image credit: @annacascarina)

“I will always invest in the best that I can afford, especially when it comes to knitwear. I love cashmere as it's super warm and soft, and merino is great for its temperature-regulating properties so it's suitable all year round. This cardigan is from By Malene Birger, a great brand for modern staples with a twist.”

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5. Shoes

Over 50 luxury shopping: @annacascarina

(Image credit: @annacascarina)

“Another thing I invest in is footwear. My Chanel sandals were a worthwhile investment as I've gotten so much wear out of them. Not all luxury footwear is practical though, so make sure you have a good walk around the shop before you invest. I would never buy expensive sky-high heels as I just wouldn't get the wear out of them. Instead, I think about my lifestyle and choose to spend my money on items that are comfortable and wearable all day long.”

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Freelance Fashion Editor

Bébhinn Campbell is an Edinburgh-based fashion and lifestyle writer and editor. She started her first blog at age 14 and went on to intern at print and digital publications in Berlin and London, including Dazed & Confused and Indie magazine.

A job at a fashion startup took Bébhinn from Ireland to Scotland in 2019, where she now works as a freelance journalist and copywriter covering everything from travel and interiors to styling advice. As a contributor to Who What Wear, Bébhinn always keeps her eyes peeled for emerging trends and looks worth writing about. She prides herself on her ability to cut through the noise and identify solid investment buys, exciting new brands and fresh takes on classic design.

In her spare time, Bébhinn enjoys perusing Edinburgh’s best vintage shops, working through her out-of-control book collection and watching dog reels on Instagram.

With contributions from