Memories of a Chronic Sale Shopper

And my mixed feelings about the global takeover of Black Friday/Cyber Monday and retailer markdown hype

Warning: This is a very long read with no pictures. If you’re not planning to stay for the ride, do at least check out these other great pieces that inspired my thoughts on this subject, which I also reference in my piece.

“Bleak Friday”, by Em Seely-Katz, guest writing for Articles of Interest (free to read)

“The Broken Economics of Black Friday”, by Alec Leach (paid subscription needed)

“Should clothes never go on sale?”, by BlackBird Spy Plane (free to read)

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I can’t remember what was my first big sale score, but I remember an early, significant one: a Mulberry Bayswater, in an incredible mirrored bronze leather.

I was inspired by a photo on The Sartorialist of a fashion editor toting one in gold; when I saw the bronze version, marked down ridiculously (I think it was 70%) during an end-of-season sale, the magpie part of my brain said YES.

It didn’t matter that it wasn’t very comfortable on the shoulder, which was my preferred way of carrying a bag, or it didn’t have any handy pockets for my phone or travel card. I loved the unexpected combination of classic-meets-high-glam. I was exhilarated by the idea that I could afford a Mulberry bag.

Another sale buy, also an end-of-season markdown, happened in a YSL boutique, back when it was painted opium red and the brand was still known as Yves Saint Laurent Rive Gauche (Stefano Pilati was the creative director). I fell in love with the Tribute tote, a voluminous take on the hobo, done in a beautiful crinkled grey patent leather. It was 50% off, and cost less than S$500, or about US$370. It was a steal.

And the list goes on. A Stella McCartney blazer I found in a warehouse sale in 2014, 80% off. My first pair of Common Projects sneakers, at 60% off. An Issey Miyake Bao Bao tote, a modest 30% off.

Most of my big sale buys were accessories, because I followed that playbook of buying my clothes on the cheap at fast fashion chains (Zara and Uniqlo were my stores of choice) and “investing” in quality accessories to elevate my look. Eventually, as my style matured, I started buying clothes from expensive brands too, fuelled by the easy access provided by online shopping — a pair of Dries Van Noten jeans at 50% off, and a Tibi wool jacket, also 50% off.

In case it isn’t obvious by now, I’m an inveterate sale shopper. And while I love most of the pieces I’ve bought, I have mixed feelings about this.

On one hand, thanks to sales, I’ve been able to afford things I wouldn’t ordinarily dream of buying. On the other hand, the markdown cycle has become numbingly frequent, and it’s a sign that things are rotten in the state of Denmark. After all, as Alec Leach wrote in “The Broken Economics of Black Friday”, “sales season only exists because brands make too many clothes to begin with”. Yes, consumers have become addicted to sales and this has distorted our idea of what things are worth, but the industry itself is broken, prioritising quick profits over sustainability, and producing a staggering volume of product, he notes.

There was a time when sales made sense — they happened at the end of a season, and sometimes there wasn’t even that much to choose from. I saved up and paid full price for things I really wanted, because it wasn’t a given that it would be marked down at some point.

Also, Black Friday wasn’t a thing in my part of the world (Singapore); I only knew of it through the news, which would occasionally report on huge crowds of people lining up in the cold to shop. It was a novelty, a one day thing, it felt like good fun.

Today, Black Friday is a global phenomenon, impossible to avoid (even my detergent is on sale??), and conflated with so many other sales (holiday sales, private sales, mid-season sales) that I’m no longer able to tell when sale season starts or ends — I’ve seen clothes marked down weeks after they arrive in stores, and it boggles the mind.

It’s also a “content mill,” as noted Em Seely-Katz in “Bleak Friday”; parsing the contents of the SSENSE sale is becoming a Substack trope at this point, to say nothing of the gift guides to follow, and media outlets dedicating entire teams to urging “smart shopping” (NYT’s Wirecutter, NYMag’s The Strategist), no doubt seeing dollar signs in the affiliated links. “Now that the sale season has become more of an incitement to produce than to consume, writers and influencers spend sale season on the clock, angling to commodify any crumb of wanting we still feel toward the objects on sale,” she wrote.

I know all this, and feel slightly nauseous and overwhelmed at the thought of it all, yet in recent years, without fail, I plot my sale buy with all the seriousness of a military strategist, knowing that if I have three items on my wishlist, one of them will likely end up discounted at some point.

It all feels a little unseemly, like I’m contributing to a consumerist culture that no longer understands the value of material goods, and the people who make them. “Should clothes never go on sale?” asks Jonah Weiner and Erin Wylie in their newsletter Blackbird Spyplane, pointing out that “we’re living in a hypertrophic era of jawnflation, marked by bogosity and illusion.” Thanks to the current retail model, clothes are priced higher to be marked down, which further discombobulate consumers’ sense of what something is “worth”, while small designers and makers can’t compete, they report.

I’ve often told myself that sales are an opportunity to access a class of goods often out of my reach, and to some extent this remains true, provided that higher-priced goods actually deliver in a higher standard of quality and design. Although people have decried the quality of clothing put out by luxury brands at eye-popping prices, it’s hard to claim that a Zara coat is as good as a Maxmara coat. The difference isn’t just in craftsmanship — a pair of COS jeans and a pair of Dries Van Noten jeans are not the same, because the latter has a design point of view that turns something basic into something artful.

These differences are not worth the same thing to everybody (I could tell my tailor was unimpressed by the pleating detail on the Dries jeans, even though it was my favourite feature on the garment). But they are worth something to some of us, which is why we are willing to pay what seems like a shocking amount of money for “just clothes”. And it is also why sale season isn’t just a chance to nab a “bargain” or buy more for less, it’s an occasion that puts the objects of our admiration tantalisingly within reach.

But the concept of accessibility is a crutch, one that allows us to conveniently ignore the labour and resources required to make something worth owning. It makes sense when deployed sparingly; it loses its value when it just means haul after haul, year after year.

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Right after I wrote the above, I ordered a pair of Studio Nicholson jeans from their website, after receiving an email that selected pieces were going for 30% off.

I’ve loved the brand’s designs for years and had tried on a pair of their trousers in a store in Melbourne earlier this year, but couldn’t justify the A$750 price tag (about US$500) on my freelancer salary. I started putting aside a bit of cash every month, thinking that maybe I could buy a pair next year if I still wanted them, and I also kept a close eye on the secondhand market for options.

But at the back of my mind, I knew there was a chance that I could buy them (or something similar) on sale. And I was right — I didn’t find the exact pair I tried, but I found a similar, less expensive pair, made even more affordable by the markdown. I did feel bad that I didn’t give my business to a local store, but being able to buy direct from the brand was a plus.

So, intellectually, I feel like I’m on the side of people decrying the sale frenzy, but in reality, I still to chose to shop a sale. And I’m sure I’m not alone. So, is there any “right” way to navigate these treacherous discount-filled waters?

I don’t know, but I would say that going down memory lane — recalling all the things I’ve bought and how I felt at the time, and what became of them — was a good exercise in questioning my motivation for shopping. I think the feelings associated with a purchase are a pretty reliable predictor of how that buy will pan out, and it’s helpful to recognise them.

The best feeling is that visceral recognition of a genuine find — it’s something you’ve wanted for a long time, or it feels like something you have always wanted. It is the best quality you can afford, and it isn’t something doomed to become a white elephant, too rarified for your lifestyle. This gut feeling is usually spot on, and it’s only tempered by financial reality — back away if you know you’re spending money you don’t have.

The most dangerous feeling is the heady rush that feels like an itch, a gnawing sensation that you “should” buy it. There’s a touch of FOMO, an urge to keep up with the Joneses (or your favourite influencer). When you look at the item, you picture a Pinterest image, rather than yourself. There is an excessive amount of justification. There is an unmistakable whiff of guilt as you add it to cart and type in your credit card number. If you’re feeling any combination of these feelings, step away, it’s not too late.

The in-between feeling is one of boredom — you buy something from the sale for the sake of buying something. For me, this manifests in inexpensive buys that don’t feel consequential, placidly adding clutter to my wardrobe, until I wake up one day and wonder, what is all this stuff? Again, step away, move on with your life.

Going through all this brought me a bit of clarity; I looked at my wishlists and for the first time in a long time, I felt nothing, and I’ve not clicked through any of the IG ads beckoning at me with discounts. And I feel good and at peace with my Studio Nicholson purchase (assuming it fits as expected).

There’s plenty more good advice out there on how not to go crazy during sales —unsubscribing from mailers, staying off social media, curating a very tight wishlist and only buying what’s on it, and so on, and I won’t repeat them. For me, it all comes down to self-examination — be as honest and transparent as possible with yourself on your motivations — and take it from there.

We’ll see how I feel in January.

How do you navigate sale season? Share your thoughts!