Style Strategy 005: shopping tips that I wish I had known sooner
I love to shop. Here's how I stop myself.
It was the sort of dress that I imagined I could answer coyly, “Oh this? Vintage Chanel,” I’d say with a smug smile. It could be photographed as part of a personal style essay flung over a mid-century modern occasional chair and an Eve Babitz novel in shot.
I found it in my favourite consignment store in the Upper East Side a few years ago when I was there for New York fashion week. It had just arrived a few hours ago and I was the first to try it on; a drop-waisted navy blue tulle Chanel mini dress with straps made of thick black satin ribbon.
The price was good — when I say good, it cost less than a full priced cocktail dress at Net-A-Porter, but certainly more than what I would usually be spending as a twentysomething year old.
The label claimed it was my usual size, but I could only just zip it up. I convinced myself that when I “got into exercise” (notice I didn’t say ‘got back into exercise’ — I’ve never been “into it”) and you know, walked more and did more regular pilates or whatever, that it would fit me. Not just physically, but it’ll be perfect for the life I’d imagine myself.
I love shopping, I love the hunt. I like to win. And this was an absolute score.
Or was it?
There are shopping rules out there, and I broke some cardinal ones. Never buy out of your size range, and try to stay within your budget. Obviously, I broke some big ones. But I told myself that I was following some key shopping rules too, like buy what you truly love, buy vintage, buy unique.
But the biggest one was buying it for a life I had imagined for myself that didn’t exist. It wasn’t about the dress, but how I thought I could be.
Storytelling is a fundamental part of being human. We are drawn to the cadence of a narrative — the highs, the lows, the introductions and the denouements. I had fallen in a trap of creating and literally buying into a story of this dress that had little to do with my actual reality.
With the influx of storytelling through social media — seeing videos of the cool girls with the xyz and the sheer amount of visual imagery of ‘inspiration’, it’s instinct to create a narrative and apply it to oneself.
I asked followers on Instagram what their favourite shopping tips are. Here’s a selection:
“Shop alone”: Yes! Don’t be swayed by peer pressure. This came through twice!
“But at the same time, only your mum [or other trusted person] will honestly tell you if something is unflattering”. I just saw on Ava Matthews’ Instagram (co-founder of Ultra Violette) where she shared a text conversation with her mother asking if a dress suited her. (Her mother is top stylist Nicole Bonython-Hines.) Her response? “It looks cheap.”
“No synthetics”
“What you should buy should be a better outfit than what you walked in wearing”
Any other tips? Share them in comments below.
These are what I keep in mind when I go shopping. I’m not immune, because I break my own rules all the time and then regret it.
Do I already own something like this in my wardrobe?
On the swing side, sometimes I tell myself buying a new item is a good idea because I own something similar and wear it all the time. I tell myself it’s practical because I’m already wearing something similar! How sensible am I! Kudos to me!
But, does it always mean that I need another version of it? Chances are, I’ll only reach for the one version of it — the one I already have.
I need to take this advice to heart more as I’m accumulating a lot of white shirts… and black pants… and yes while there are slight differences in cut and fit, I have a few favourites that I am drawn to time and time again.
The exception to the rule is if the well-loved original is falling apart and cannot be salvaged.
If it wasn’t a designer label but instead was a no-frills chain store brand, would I still want it?
This helps separate actually liking the design, and being sucked in by (slightly discounted) designer. This also helps separating it from what you like, to the social signifiers of what you want it to tell other people, which I covered in the last edition of Style Strategy about how to select a handbag.
What would I wear it with?
If I look at something and wonder to myself “That would look great but I need that new shoe shape and it’ll be perfect with xyz bag that I don’t own…” then no. Because that requires buying a new outfit and life to suit it, and that really can’t be justified.
Sleep on it
Love sometimes is at first sight, but if it’s really meant to be, it should last the distance. If it sells out… well, that’s a sign, and you know what? There’s always going to be another great pair of shoes or dress out there for you.
Use alerts and wishlist functions
I was such a big proponent of this that when I left my job at Vogue, my farewell card (traditionally a mock-up of a magazine cover with fake cover lines) had “Your wishlist is my command — how to never, ever miss out on a Net[-a-Porter] sale” because I used to tell people to use the wishlist function all the time.
To aggregate it all, I also use the app Carted where I can add items from any website and it’ll alert me if prices have gone up, down, if it’s sold out or coming back in stock.
Am I buying it for my future self?
Now, I love forward planning and thinking for the future. But sometimes this can be another trap because the future is so amorphous and changeable, I can basically talk myself into anything. If it’s summer and I’m buying something for winter, there’s a far higher chance that I’ll get over it by the time it’s seasonally appropriate.
How does it make me feel? And can I get that feeling from my existing wardrobe?
Sometimes you see an image or get an idea in your head about how a certain item is going to complete your life. But is it that particular item, or the vibe that it’s creating? Fashion editorials are primed to create a mood but they’re image-creating, not for outfits for life.
I love images like this, below.
But as I wrote in Style Strategy 001, it’s not telling me exactly that I should be looking for bright pinks and blues. It’s about creating a mood — which will be covered in a future edition of Style Strategy.
What feeling does it conjure up in me? Fun, surprise, delight. How can I create this in my own clothes rather than buying something new?
What I love about it is the layering, the irreverence, the contrast of dressy (sequins and feathers and organza/chiffon) with more casual clothing (printed shirts, flat sandals). The feeling it’s giving me is FUN. Joyful. Surprising.
It’s not something that can be solved with a single item, but it’s how you put it all together.
Shopping, for most of us, isn’t just about filling our closets. It’s about fulfilling fantasies, collecting pieces of an identity we think we should have. Social media is full of girls whose wardrobes are aspirational mood boards, where every purchase fits into a narrative. But real life rarely zips up so easily, and isn’t made through purchases.
If you enjoyed this, explore other editions of Style Strategy, my series on personal style:
And consider becoming a paid subscriber. You can upgrade your subscription here.
As a paid subscribers, you will receive:
Access to my weekly series on finding and evolving your personal style, ‘Style Strategy’, kicking off from today — for paid subscribers only
Monthly brand deep dives on a fashion or beauty brand via a business perspective, covering marketing, brand (tone of voice and imagery) and digital
One bonus recommendation newsletter per month for paid subscribers only
This will be in addition to my usual content of my weekly recommendations (READ/LISTEN/EXPLORE) minus the one for paid subscribers only and Screen Tests (interviews with interesting people).