I Just Asked 8 Very Stylish Women About the Best Item They've Ever Bought

Some of us live for the thrill of newness, some of us thrive on a solid purchase and endless rewearing. I personally reside in the latter camp, and can spot that kind of fashion sensibility in someone else from a mile off (or during a blurry late-night Instagram scroll). With the New Year comes both a desire for trends and updates, but also an awareness of rebooting in other ways too. How can I be more mindful of what I buy? How can I make sensible purchases instead of endless ones? How can I really invest in items that stand the test of time for my wardrobe? The last question is a particularly pertinent one for now because one woman's failsafe blazer is another woman's never-even-took-the-tag-off wasted purchase. 

I'm not sure at which point in my fashion industry career it became so radical to not buy something new (my mum's generation had to make every piece last), but the idea didn't take long to completely shift our habits. With hashtags such a #nonewclothes and #thisoldthing now racking up 32.5k and 17.8k posts respectively on Instagram, and a slew of influencers, designers and brands extolling the virtues of buying better and buying less, some corners of our world are breaking free of the fast-fashion chains and celebrating the concept of perusing one's own wardrobe. The resale market is on the up (Vestiaire Collective reported to us that last year sales increased by 144%) and where once it was considered inferior to buy secondhand, pre-loved, or whatever else you'd like to call it, now kudos is an almost instant by-product. 

Below are seven very cool women with totally different aesthetics, yet each of them has managed to find that one holy grail item—the piece that travels with them through seasons, trends and moods. There are a few common threads, such as investing in quality handbags or tailoring, but stylistically each piece stands up as unique and personal to their individual looks. Keep scrolling to see the best-ever fashion items these arbiters of taste told me all about.

After seeing Belfast-based content creator Tanice post about this seemingly simple grey jacket alongside a picture of her father wearing it, I knew I had to learn more about this special item. "I inherited this blazer after my dad passed away in 2015," she tells me. "I thought that I would keep it as a more sentimental piece but that changed quickly as I reached for it a lot more than I first expected."

What would have once been a super-smart item for her father has been reconfigured into her wardrobe using new and interesting laid-back outfit ideas. "I usually wear it one of two ways: for casual days over comfortable loungewear with clean sneakers, or for a more put-together look, over a white T-shirt, black trousers and heels."

"This blazer means the world to me," she says. "Firstly because it was my dad's and secondly because it is older than me. I have pictures of him wearing this piece through the decades and I hope to do the same with it and pass it on to someone else."

Combining a blazer over a tracksuit is a great idea for moving into this era of working from home and staying comfortable while looking smart. Although you won't be able to pick up Tanice's exact blazer, there are similar boxy styles out there, and you can always (virtually) raid some charity stores for '70s, '80s and '90s menswear to get the perfect fit for you.

best rewear fashion items: Loewe puzzle bag

Photo:

@_jessicaskye

Many of the Who What Wear UK team watch Jessica Skye's wardrobe very closely. She's very good at selecting items that are classic but not boring. Case in point? Her black Puzzle bag from Loewe that she bought in December 2019.

"It was a very special treat to myself and something I thought long and hard about. Especially with the price tag I knew this couldn’t be an impulse buy, it also needed to be practical and chic," she says. "I wear this bag with nearly all of my everyday looks, that’s why I always invest in neutral-coloured handbags that aren’t heavily logoed so they go with everything else in my wardrobe."

best rewear fashion items: Loewe puzzle bag

Photo:

@_jessicaskye

This neat little number can be worn in multiple ways, and her looks range from whimsical to utilitarian. "I’m an avid blazer wearer and team my Loewe Puzzle with multiple blazer combinations and I love that this bag can be worn multiple ways—either across the body or held. I wear it with almost everything in the wardrobe but my go-to looks are with a suit or a crop blazer, floaty skirt and chunky boots."

best rewear fashion items: Loewe puzzle bag

Photo:

@_jessicaskye

Although this item may not hold a great deal of sentimental value yet it does provide polish and practicality by the bucket load. "Having a practical yet chic bag is imperative in my everyday capsule wardrobe and one that can be worn slightly differently depending on the occasion or outfit, versatility is key when in investing in handbags," she tells me.

best rewear fashion items: Loewe puzzle bag

Photo:

@_jessicaskye

Jessica isn't the only one to have discovered the benefits of this creation. Net-a-Porter explained to us only recently that this particular style has been selling like hotcakes since lockdown began, with women who have disposable income finally choosing this moment to invest in a luxury handbag that withstand the test of time.

best rewear fashion items: white lace coat

Photo:

@msorrig

Not every best-ever purchase has to be classic or simple. That's why it was interesting to discover that Scandinavian fashion lover, Mette Sorrig, chose this lace vintage jacket as her key item. "It can be used for so many outfits," she tells me, and the pictures here are certainly proof of that.

best rewear fashion items: white lace coat

Photo:

@msorrig

"I got it approximately five years ago and I bought it a flea market. I totally love it and will keep it forever," she says. "It always gives this vintage vibe to an outfit, which I love. Old and new things can go together hand in hand."

best rewear fashion items: white lace coat

Photo:

@msorrig

"A good item is one you can use both summer and winter and this piece does both," says Mette. As you can see here, she's wearing it more like a dress at Christmas with fluoro-pink tights and heels, but it works just as well as a lightweight piece of outerwear during the warmer months.

best rewear fashion items: white lace coat

Photo:

@msorrig

This cowboy boots–and-leggings ensemble, she says, shows one of the oldest outfits highlighting her key piece, but it still looks entirely current. Mette explains that even if her style changes over the years, it doesn't affect how she feels about wearing this jacket, which is the sign of a being able to find something that truly reflects your personal style.

best rewear fashion items: black tuxedo jacket

Photo:

@biancaffoley

I wasn't surprised to find that Bianca, an advocate for sustainable style, had a good option for this story. "I have a gorgeous tuxedo-style blazer that I got a few years ago," she tells me. "Pre-lockdown, I wore it at least three times a week as it’s so versatile, wearing it with casual dresses, jeans and even smarter, more corporate or office-appropriate looks." 

best rewear fashion items: black tuxedo jacket

Photo:

@biancaffoley

These days Bianca uses this classic piece to look "more dressed up for the endless Zoom client calls!" combining it with a more flouncy spring or summer dress for a contrast.

best rewear fashion items: black tuxedo jacket

Photo:

@biancaffoley

The tuxedo first became a more regular fixture in women's wardrobes in the '70s when Yves Saint Laurent adapted the classic men's tailoring piece to create Le Smoking—a more fitted version of its original silhouette. "It’s one of those key pieces that I think everyone should have in their wardrobes," says Bianca. "It’s chic, classic and endlessly versatile!"

best rewear fashion items: black tuxedo jacket

Photo:

@biancaffoley

The tuxedo started life as an eveningwear essential but it has since become an easy piece to sling on during the day. It can instantly sharpen up relaxed outfits like Bianca's cute gingham dress-and-ankle-boot combination here.

Dutch fashion writer and consultant Stephanie is a leading light for re-wearers everywhere—she's been sharing her clever finds on Instagram for years now. And the piece she feels most proud of? A secondhand Jil Sander handbag. "This is truly a bag that goes with almost anything in my wardrobe. The tan colour works great with black, white, grey, green…" and the many ways in which she has worn it speaks to that point. 

The Sombrero bag, as it's called, was tracked down by Stephanie on Vestiaire Collective three years ago. Since then she's been toting it on repeat, from the city to the beach and back again. "A few years ago, I turned my wardrobe into a capsule wardrobe full of long-lasting, versatile pieces that all go together. Which makes it so easy to style different pieces together," so she finds that she still wears and styles this easy piece in the same way that she did when she first bought it. 

"This bag is still one of my favourite pieces in my wardrobe. I love the shape, the size and the colour. I’ve worn it so many times that it has started to show, but the patina makes it even more interesting to look at."

"Many women compliment me on this bag, especially older women, which I love. I’m thinking about getting it repaired at the Restory, which is an amazing service for designer pieces," she says. A great tip to take away—look after the items you love and they'll appreciate you back in return!

best rewear fashion items: gold chain necklace

Photo:

@joy_monty

Who What Wear UK's Shopping Editor Joy Montgomery is a vintage enthusiast and always manages to track down those special items that are worth buying secondhand thanks to their unique detailing or alluring price point. A very good example? Her excellent chain necklace. "I can't remember the exact store where I discovered the necklace, but knowing me it was probably one of the charity shops on Marylebone High Street that I used to peruse during lunch breaks in my first job. I've never really been much of a jewellery person, but at this point in time, as I was starting out in fashion journalism, I wanted something to make my outfits feel more pulled together and grown-up," she says. 

best rewear fashion items: gold chain necklace

Photo:

Getty Images

"This particular photo is from one of my first fashion weeks, and it was exactly what I needed to make a bit of a statement," she says. "I still rely on the elevating powers of a single powerhouse jewellery piece, such as this vintage necklace, that can be thrown on with everything from dresses to white tees. That being said, I can't see myself wearing this crop-top–and–midi-skirt combo now."

best rewear fashion items: gold chain necklace

Photo:

@joy_monty

Instead, you'll be most likely to find Joy using this statement choker as a piece to layer over demure dresses with high necklines. It brings extra pizzazz to an already vibrant outfit but also does a lot to liven up simpler looks too.

best rewear fashion items: gold chain necklace

Photo:

@joy_monty

"I think it's a nice reminder or my enduring love of vintage fashion—something I hope will never fade—and also the power of a well-chosen classic. I would love to apply the same rule to everything I buy, but sometimes you don't know something is truly ageless until you have the benefit of hindsight!"

A keen restyler and expert within the hashtag realm of #nonewclothes, I wasn't surprised to see that digital marketer Chloé actually had multiple suggestions for me of the items she uses on repeat. Ranging from a white one-shouldered dress she designed herself to luxe dressing gown robe, it was actually this pair of Mango snake-print boots that really caught my eye. How brilliant to A) find something on the high street you can use time and again, and B) for it to not be basic by any stretch of the imagination. "If there was one thing in my wardrobe that makes me feel sexy and like an IG baddie, it's these boots without a doubt!" Chloé says.

"I can't even remember when I got these boots but from the moment I saw them, it was a wow from me," she tells me. "The first time I wore these, I believe was for a shoot in Portugal. I wore them with an oversized knit for another cool and effortless look."

"I have worn these countless times. They are so easy to walk in, not super high and intense either. I have worn these with dresses, mini dresses, maxi dresses for layers and even teamed them with jogging bottoms. Every time I remember or see them, I dig them out of my shoe cupboard and create a brand new look in them," she says, pictured here wearing a whole outfit of items she pulls out on the regular.

The eagle-eyed amongst you may recall that we documented model and content creator Natasha's closet for our Best Wardrobes in Britain franchise many moons ago. Back then we were impressed by her jacket selection, and it turns out that her best-ever purchase is indeed a little black leather biker from Topshop in 2016. "It has been my leather jacket staple ever since," Natasha says. "Some high-street leather pieces have come and gone, but this one remains."

"In the winter, I layer a T-shirt then turtleneck underneath, so that I can leave it open, as it becomes too bulky to button up. In the summer, I wear it over a slip dress or T-shirt, in case I go somewhere air-conditioned and I need it to stay warm. It goes with pretty much everything. Leather biker jackets are that one staple item which works in many ways," she explains of this classic moto style. Not only does it get plenty of usage in her home city of London, but it also appears to go with Natasha on all of her travels—a handy item to pack or wear on a plane.

"It is one of my valued pieces. I have items way more expensive than it and I wouldn't cry over losing them. But items like this one is one of them gems that you can never get again, for that price and I value it more than some designer pieces in my wardrobe," she tells me. 

"I can't wait for it to reach a 10-year milestone and see how it fits on me and how it has maintained its shape," she says. And we'll be watching! 

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