Buying things you’ll actually wear

Interrupting your Black Friday scrolling with some strategies for sale season.

Nov 21, 2024

I recognize there are two ends of the spectrum when it comes to Black Friday/Cyber Monday shopping: those who don’t feel like they need anything and will skip it (if you’re feeling this way, you probably don’t need anything!) and those who use the weekend as an excuse to shop till they drop.

Last year, I found myself somewhere in the middle—if not more on the side of “I don’t need anything else” after investing in a really great winter coat and knee-high boots (I got both on sale during BF week.) This year, I admit I have more items on my shopping list as I find myself trying to fill in some key gaps in my closet (mostly nicer sweaters and a few accessories).

I think it goes without saying that buying something just because it’s on sale is never a great idea. But if you have something already identified as a need, I think it makes the most sense to get it while you can take advantage of a discount. Personally, this is how I shop. I don’t buy a lot throughout the year and will save my money to spend it during a sale.

With a longer shopping list this year, it feels like I’ve been putting a lot more thought into what I want to buy, prioritizing and scrutinizing each piece to make sure I end up with things I’ll actually wear. Here are some strategies I’m using to stay focused.

Sticking to my list—and ignoring the rest. Pretty straightforward, right? Except I keep catching myself updating my shopping list and finding excuses on why I “need” something else. I’ve now cut myself off from adding more to it because there’s no point in having a list if it’s growing out of control.
Photo: @eliinaolofsson / A few things from my list and in my cart: Black/silver leather belt + mini Chrystie bag in Espresso (currently 25% off) via s_dang + cashmere triangle scarf influenced by @Angie’s styling ideas here + leather slip-ons + sheer turtleneck + silver bead necklace
I feel like this may already be a given… but taking stock of what I have in my closet to make sure that what I’m buying is a) not similar to anything I already own (unless it’s to replace an old, worn-out piece) and b) something that would work with the rest of my wardrobe. My goal when shopping is no longer just about buying something I like, but to make sure I’m building towards a wardrobe full of pieces that work well together.
Letting inspiration and intuition guide me. I find it’s helpful to gather inspo and save photos for reference, so when I come across something I like, I already have ideas on how I want to wear it. This helps limit those scenarios of buying clothes impulsively because I think they’re cute and then struggling to find ways to style them.
A peek into some fall inspo I saved on IG
The other side of this, though, requires practicing some restraint and discernment so you’re not just buying a whole new outfit because you saw it on someone else. While I will save some photos of aspirational looks, most of what I save for reference are outfits comprised of mostly similar pieces I own. And whatever piece I’m missing from those references that I want to buy has to work for me, my style and my life. This is where the intuition part kicks in.
At this point, satin pants are still an aspirational piece for me as I’m not sure how much wear I’d get out of them but I still save photos for reference. These satin pants have been on my wish list forever and are currently 25% off for US customers with the code HOTELVINCE. (Photo: @chloenpinchasick)
References like this (jeans + oversized sweaters) are more realistic for my lifestyle. Similar sweater here, which I recently purchased on sale. (Photo: @smythsisters)
I’ve noticed many stylists on Substack talk about exercising your intuition to develop your personal style, and this naturally ties into shopping, so you’re not spending money on something you won’t wear. This quote from a previous What’s In Q&A with
Irene Kim (김애린)
sticks with me always:

It really comes down to the maxim: Know Thyself. Know what you love and feel good in. Know what feels like YOU when you put it on. At the other end of the spectrum, get used to listening to your intuition when something doesn’t feel right, even if it’s the “It thing”, the “must have”, or supposedly “works for everyone”. As you filter out the noise and embrace what makes you feel good (no matter how weird or obscure), gradually you’ll better hone in on your personal style.

Being extra picky and selective. When something is on sale, it can be tempting to compromise on certain things and justify the purchase. I’ve done this—buying sweaters that were close to but not exactly the right silhouette or colour I was looking for just because they were on sale. I tend to regret those purchases months later. I’ve learned it’s never a good idea to settle for something you don’t love; waiting for the right piece to come along is always worth the wait.
Top photos: @ciarahughesstyle / Laura Harrier via @whowhatwear.uk / Pinterest / Pinterest. I’ve been looking for the right polo sweater that had a similar vibe to the photos on top, and passed up on several options I came across that were on sale because they weren't exactly the right fit. The J. Crew option (left) seemed a little too cropped and the H&M version (right) was less structured. I’m glad I waited it out because I ended up finding a sweater at Arket (middle) on sale, which was exactly what I was looking for.
Of course, leaving some breathing room between when you add-to-cart and when you actually check out always helps. I’m trying to be more intentional by taking my time, closing my browser window, walking away from my desk or phone, and simply sleeping on it before making a purchase. I still feel panicked when I see a piece is close to selling out or there’s limited sizing left, but one thing I try to remind myself is that there’s always next season.
Our desire to buy something new never ends, and if we miss out on a particular piece one time, it’s not the end of the world. Most of the time, pieces I wanted from previous years are available again this year. And if they’re not, I figure maybe it wasn’t meant to be. There’s always something newer and better to look forward to.