The Fashion Moments Our Editors Regret Most

Personal style is a topic we cover in depth on Who What Wear Australia. Fashion is more than just clothes. What we wear can help define who we are, signify a moment in our lives, and can affect our confidence and mood. Don’t lie—a new pair of shoes or a perfect ten outfit always makes you feel good. While we always covet and obsess over celebrity and street style, more often than not, it’s real girls who provide the most inspiration—the girls you pass on your way to work, or stand behind at the ATM line, or behind the counter at your favourite vintage store. Today, we’re talking real-girl personal style. Our editors are opening up about their biggest fashion regrets, and what they learnt from them.

Keep scrolling to discover what they’d do differently now, and then share your biggest regrets in the comments below.

Age: 31

How old were you when you started to appreciate fashion? 25… I feel like I was a late bloomer. I found my style late.

What’s your favourite piece in your wardrobe? An Apiece Apart black midi skirt—because the material is heavy, it looks like magic when I walk.

Is there an outfit that makes you squirm when you see a photo of yourself in it or when you think of it? Describe it.

I feel bad for myself when I think about what I wore to my first high school disco. Let me start by saying I was wearing Converse and a dress well before it trended! But when I arrived someone teased me saying “nice shoes”, and I always want to hug myself when I think about it. I wore black Cons with a blue floral dress.

Has there ever been an item you really wanted to buy but didn’t bite the bullet and still regret it?

I probably should have spent the money and bought the Acne Studios Mock Leather Jacket ($2200). I got a nice one from Maje but it is unlined and the cuffs have come undone after one season. So now I need to get it fixed.

Are there certain pricey pieces you’ve bought over the years that you now regret?

I have bought a couple of random pieces—like a Stella McCartney pin-striped skirt I was sure would revolutionise my wardrobe. I’ve worn it twice. And then Alexander Wang over-the-knee boots. They were an investment buy but they’re so hard to walk in I’ve only worn them maybe five times. And each time with immense pain. I remember we had a fire drill the first time I wore them and I had to basically crawl down four levels of stairs in them.

What have you learnt from your regrets?

I guess it is to always buy the piece you really want, not the copy. And then, a regret today will more than likely be #trending in years to come. Fashion is transitional.

What do you do differently now?

I’m a super curated shopper. When I do shop, I spend, and usually on an item I’ve had typed out in the notes section of my phone for a month.

Age: 29

How old were you when you started to appreciate fashion? I’ve always loved fashion, but probably didn’t begin to truly appreciate it until I was in my low to mid 20s.

What’s your favourite piece in your wardrobe? My Gucci Soho Disco Bag ($1365).

Is there an outfit that makes you squirm when you see a photo of yourself in it or when you think of it? Describe it.

I think one of the worst outfits I’ve ever worn was to one of my best friends' 18th birthday party, which was held in a shearing shed at her parents' farm. I wore dark denim low-waisted bootleg jeans and a dark denim collarless jacket (not the cool double denim look, rather the daggy Canadian tuxedo look), a pale pink jersey material belt (remember those?), brown, zip-up mid-calf boots, a chocolate brown turtle neck, thin pale pink knitted scarf looped around my neck, and baby pink plastic hoop earrings. This horrendous outfit was teamed with hair that featured blonde streaks (there was no such thing as balayage 10 years ago!).

Has there ever been an item you really wanted to buy but didn’t bite the bullet and still regret it?

I still regret not buying the most perfect little black Ellery dress a few seasons ago.

Are there certain pricey pieces you’ve bought over the years that you now regret?

Printed or bold coloured evening dresses that have now dated and I wouldn’t be seen dead in them.

What have you learnt from your regrets?

To always go for quality over quantity and classic over trends.

What do you do differently now?

I buy less, but more considered pieces.

Age: 27

How old were you when you started to appreciate fashion? I can’t remember a time when I didn’t care about fashion. #Lame but true.

What’s your favourite piece in your wardrobe?  My Balenciaga Studded Leather Wedge Sandals ($1425).

Is there an outfit that makes you squirm when you see a photo of yourself in it or when you think of it? Describe it.

Thankfully there are no photos (that I know of), but for an entire year when I was 15 years old (around the time I started shopping for clothes myself), all I wore was head-to-toe chocolate brown. Chocolate brown must’ve been a ‘thing’ at the time, because my go-to outfit was a chocolate brown Billabong zip-up turtleneck jacket (which is kind of trending now), a pair of chocolate brown bootleg corduroy pants, chocolate brown knee high boots (which I obviously wore under the pants. So weird), and a chocolate brown sling bag embellished with diamantes. I feel like an imposter when I tell people now that I’m a fashion editor.

Has there ever been an item you really wanted to buy but didn’t bite the bullet and still regret it?

I had the opportunity to buy the Céline Silk Foulard Print Shirt from S/S 11 (the one Kanye West wore) and passed it up because I couldn’t justify the spend at the time. Five years later I’m still thinking about it. Even though the print has been mimicked a thousand times over, nothing beats the original. Hey Kanye, if you’re done with yours, I’ll happily take it off you.  

Are there certain pricey pieces you’ve bought over the years that you now regret?

I don’t even know where to begin. When I started my first ‘adult’ job, I became so obsessed with designer sample sales, I’d go and buy everything just because it was ‘cheap’. Note to self: $300 on a skirt you’ll never wear (because you actually hate the purple floral pattern), is not cheap.

What have you learnt from your regrets?

Now, I consider every purchase and don’t hit a sample sale unless I have an actual piece in mind that I want to buy. I also keep an email in my drafts titled “Wish list” and I add shopping links and screenshots in as I come across pieces I like. If I keep thinking about them, then I come back to them and go through with the checkout process.

What do you do differently now?

I definitely don’t wear head-to-toe chocolate brown anymore (although, the colour is coming back, so maybe I should reconsider). I buy less, and always make sure the pieces I’m buying actually fit into my wardrobe with what I already own.

Age: 30

How old were you when you started to appreciate fashion? When I was 18 I had a very basic boyfriend and when I started experimenting with my style he was all like, 'What is Wheels & Doll Baby?' I went from skin-tight jeans (with zips down the sides—don't ask) to '50s-style skirts overnight and there was no going back. (Helped me ditch the basic boyfriend, too.)

What’s your favourite piece in your wardrobe? My Acne Studios Leather Biker Jacket ($2200) (see pic above, LOL).

Is there an outfit that makes you squirm when you see a photo of yourself in it or when you think of it? Describe it.

Top of mind would be my year 10 formal dress. It was long with a halter neck, and made from orange and hot pink shot silk. I was obsessed with a red carpet photograph of Charlize Theron wearing something similar so my mum asked her mate (who also happened to be the seamstress for The Wiggles—chic) to recreate it for me. In hindsight it was pretty unflattering, but at the time I loved it sick. I take solace in that fact, but I still cringe when I see photos from that night. 

Has there ever been an item you really wanted to buy but didn’t bite the bullet and still regret it?

Not really. It’s rare I see something so amazing I MUST have it I do, however, deeply regret passing on the most perfect pair of high-waisted black denim cut offs to a friend about five years ago. They were too big at the time, but would fit me perfectly now.

Are there certain pricey pieces you’ve bought over the years that you now regret?

After I landed my first full-time job in my late teens I went through a phase of buying a new pair of shoes almost weekly. For some reason I even purchased a few pairs that were half a size too small “just because”. (Teen me = dumb.) Not only could I have spent the equivalent chunk of change on a few pairs of designer heels (that actually fit), I ended up with soft tissue damage to one of my feet from squeezing them into too-small flats. It was pretty stupid but you live, you learn.

What have you learnt from your regrets?

A few things. I’ve learned to resist the panicky feeling I sometimes get around snapping things up on sale or purchasing before something sells out. Now I ask myself, If this dress/tee/pair of jeans sells out in my size am I going to go home and cry about it? More often than not the answer is no.

What do you do differently now?

I’ve grown into both adding practical pieces to my wardrobe and spending the bulk of my money on classic wear-forever pieces. I used to drop $400 on printed wear-once dresses like it was nothing, but now I’m more likely to do so only on something like a well-cut blazer.

 

Opening image: Getty Images

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