10 Stylish Women I Know on the Biggest Fashion Purchase They've Ever Made

The word "investment" is thrown around a lot nowadays, especially in 2019, when "throwaway fashion" has become a dirty term. We're all looking for longevity from our purchases. However, how do you decide that something is worth investing in, and how do you know when it's the right time to make the biggest purchase you've ever made?

Spending way more money than usual on a single item can be hugely daunting. I was so overwhelmed when I bought my first big purchase—a Gucci Soho bag—that I forgot my PIN number and had to step away for 10 minutes to calm down enough to remember it, (despite the fact that I had agonised over this decision for six months). Turns out this was the right buy, as I have used it constantly ever since and still consider it one of the most long-lasting pieces I own.

I asked some of the most stylish women I know about the biggest fashion purchases they ever made and how they decided it was worth taking the hit. Most people's first big purchase is a handbag—and more often than not, this is an item that was bought to mark the start of a new dream job or another major life event. Other investment items include jackets, statement dresses and ankle boots. Below, you'll find many classic items, such as Celine's Madame Boots and an Acne Musubi Bag.

Keep scrolling to see how 10 of the most stylish women I know decided on their biggest fashion purchase.

Mulberry Bag


Erica Davies

"I remember saving up madly to buy the original Mulberry Roxanne bag when I landed my first job as a fashion editor. I chose the natural tan colour because I figured it was neutral enough to work with everything I owned while being a classic choice that would work over time. It took me about six months to save up for it, but it was a lovely feeling when I eventually went in to buy it! I probably have others, but that’s the one that meant the most as it was a treat to myself for getting the job I really wanted." — Erica Davies, fashion influencer

Loewe Statement Dress


Slip into Style

"My biggest investment piece was a runway dress from Loewe with a silk bra and a shearling trim. I bought it because last year I decided to start a small collection of runway designer clothes: unique, rare, eye-catching pieces that you wouldn't see on everybody. I spent hours looking at runway photos and videos, and when I saw the Loewe dress—a mixture of outerwear and underwear—I knew I had to have it. The day I bought the dress is also the day I decided to cut all my hair in a short tapered cut. That dress was like a celebration of the new me." Ellie of Slip Into Style

Wandler Bag


Joy Montgomery

"The term 'investment' is a relative one, but as a lifelong high-street devotee (by financial default), it takes quite a lot for me to drop a significant amount on one item. Perhaps my penny-pinching student mindset is still operating on a subconscious level. But when I got this job, I wanted to treat myself and invest in a good-quality bag that will survive the seasons and work for both informal and dressed-up occasions. Wandler's Hortensia was the answer to my prayers, and thankfully, I can say that I've maxed out on cost per wear, as I use it for everything from work to weddings. I'm careful to keep it in good condition by cleaning it regularly, and I have no doubt it'll serve me for years to come." — Joy Montgomery, freelance shopping editor

Dior Tote Bag


Emma Rose Thatcher

"My biggest investment was the Dior Tote bag I got last year. It was a present for my 10-year wedding anniversary, and although it's an extravagance, I've used it nearly every day since. When I originally wanted it, it was sold out, which made me want it even more, making the decision to buy it a little easier when it did become available. It's perfect for carrying my laptop, diary and everyday necessities. Plus, the colour means it goes perfect with denim. I'm in love with vintage Dior, so I'm hoping this bag will stand the test of time and I'll still be using in 20 years." Emma Rose Thatcher, influencer

Celine Madame Boots


Ropes of Holland

"My biggest investment was my Celine Madame boots. I had mulled it over for a while and decided I could wear them with pretty much anything. Cost per wear, cost per wear! They sold out quickly, and by the time I was ready to buy them, I couldn't find them anywhere. I ended up paying over the odds for them because of their rarity, but they were the best investment. I actually had my friend Bettina Looney source them for me via her personal shopping team. I still stand by my investment and secretly am counting down the days until autumn so I can bring them back out!" Lindsey of Ropes of Holland

Suede Fringe Jacket


Hannah Almassi

"I recently spent a good few weeks humming and hawing over a suede fringed jacket from L'Agence. After failed attempts to buy something secondhand (and cheaper) on Depop or to get something shipped over from the U.S. on Etsy, I decided that this was one of those occasions where the gap in my wardrobe for a decent, cool spring jacket needed to be filled with something that would definitely fit, last a long time and be an item I could return if needs be. 'Buy cheap, buy twice' is the old adage, and in certain fashion instances, that can be true. Now, I have a jacket that looks cool with almost everything I own, will age well thanks to the grey/khaki suede, looks a little bit vintage and is really quite timeless without being boring." — Hannah Almassi, Who What Wear editor in chief

Chanel 2.55 Bag


Emma Hill

"My [big investment item is my] vintage Chanel classic flap. It's iconic, and Chanel usually holds its value, so I figured I had nothing to lose. It's so easy to wear with any outfit—be it my staple jeans and T-shirt, or something more dressy for an evening or occasion. Oh, and I went for vintage because I loved the idea of it having a bit of history behind it." Emma Hill, fashion influencer

Jigsaw Blazer



"One of my biggest investment buys was a black jacket I bought from Jigsaw. It was around £200, and I bought it just before I got my job at Who What Wear. I knew I'd get so much wear out of it. Over three years later, it hasn't aged in terms of trends, as it's such a classic piece, and it's worn so well I'd even say it looks nearly new." — Elinor Block, assistant editor

Acne Msubi Bag


Alexis Foreman

"I think my biggest spend has been £850 on the Acne Studios Musubi Bag I got nearly a year ago. I thought about it for about a month and decided to go for it after selling some of my old pieces. I went into the Dover Street store with the cash to buy it; I wanted to physically try it. I didn't use it for about three weeks, as I was too nervous and wanted to make sure I'd made the right decision! I kept trying it with different outfits. Once I did start using it, I knew this was a wise purchase. It goes with pretty much every outfit I wear, and because it doesn't have any metal hardware, I think it makes it that much more versatile. Excellent cost per wear so far!" Alexis Foreman, fashion influencer

Chanel Linen Bag



"My biggest investment purchase is definitely my vintage Chanel bag in beige linen fabric with bamboo handle. I was looking for the perfect Chanel bag that I could see myself with during my whole life, so when I found it at Vestiaire Collective, I knew it was the right one. It was everything I dreamed about in a Chanel bag, since I was not looking for the most classic ones." — Hanna Marzouki Widlund, fashion stylist

Next up, see our guide to the key trends for spring/summer 2019.

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