5 Pieces I’ve Worn at Least 300 Times
Their price-per-wear stats? Impeccable.
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A stranger recently DM’d me on Instagram to comment on my clothes, and I haven’t been able to stop thinking about it. They wrote:
“I hope this doesn’t come out wrong, but I love how you wear things for years and years. I was just watching some influencer story, and she said, ‘I just got a new Amazon haul that I’ll try on for you,’ and I actually really like this person (and you probably know her), but it’s just so much consumption. How do you continue to get excited about things when you just get a giant package every day? It’s always refreshing to see you recycle from many years ago.”
Later that week another person messaged me to note that they find it interesting that so many of my clothes are “older.” Meaning: purchased more than five years ago. This other person, like the first one, wasn’t being a troll in the slightest; they were also reacting to what we tend to share on social, which is newness, not necessarily real life. (And trust me, I’m aware of the irony at hand, especially given the fact that shopping content makes up a great proportion of both my day job and this newsletter.)
I’d never really thought about the fact that I rewear things so many times, or that so much of my wardrobe is older, a phrase that still makes me laugh. I’ve dressed this way for decades, for a variety of reasons.
1. I’m sentimental, so I tend to be a saver.
2. I’ve always had more of a retro silhouette, so the latest trends haven’t always been the best fit for me or my body. That in turn has led me to secondhand and vintage clothing, starting in high school.
3. Vintage clothing is usually made from much better fabrics than you find in fast fashion and can be found at approximately the same prices, which makes it a no-brainer. Of course, thrifting takes a lot more time than ordering online, so it’s not for everyone.
4. Uniform dressing has been my thing since the early aughts. When I was 22 and started working at Elle in New York, I was overwhelmed by how stylish and seemingly wealthy my colleagues were. Rather than stressing myself out every morning over what I wore to the office, I identified a handful of silhouettes and key pieces I liked and basically just mixed and matched each day. Like Garanimals, but for me!
And yes, it’s better for the planet, but I cannot take credit for thinking about the environment back then because I simply wasn’t that aware. Though, obviously, I am now.
Long story long, this whole discussion got me thinking about the true workhorses of my wardrobe. The things I’ve worn over and over and over again, where the price per wear is now simply pennies or even less! I thought I’d share a few of my staples, and maybe you should share some of yours with me?
As a warning for anyone who is triggered by expensive things, some of these pieces are pricey. I’m pretty good about finding a deal or a sale, or simply saving up for the things I really want to buy, but I know that can be annoying for some folks or just make people feel a way. I think the incredible editorial team at Who What Wear do an amazing job at finding things at a wide range of price points and identify steals galore on a regular basis, if you’d like more of that content. But if you’re interested in my personal must-haves, the things I’ve worn at least 300 times? (I’m not kidding about that number.) Well, stick around, because I have a few!
Oversized, Classic Leather Motorcycle Jacket
In 2016, I bought a big, heavy, very traditional black leather motorcycle jacket by the brand Iro, which I found on The Outnet. It’s boxier than the brand’s classic Ashville Jacket, and longer in the body than its Han Leather Jacket. It’s probably most like the Swata Leather Jacket, of all of Iro’s current offerings.
I think the reason I’ve worn it so much—and the thing to keep in mind if you choose to shop for one—is that it’s never been a trend-driven style. The lines are clean, the proportions are simple, and the material is timeless. There’s always going to be an of-the-moment version of the black leather moto, but those styles do tend to look dated after a few years. If you pick an option that feels Ramones-adjacent (they wore Schott Perfecto Jackets, FWIW), I’m pretty confident you will get at least a few decades of wear out of it.
Simple Pointy Pumps
Some folks are going to yell about the fact that I’m recommending a pair of designer pumps, with the totally fair criticism that you can buy a version of this at a much lower price point. And they’re right.
However, as someone who has been able to wear different versions of this exact shoe from probably more than 20 brands over the years (a perk of borrowing things for photo shoots), I can say that Gianvito Rossi’s 90 mm version is far and away the most comfortable and durable. That said, I know not everyone wants to wear a 3.5-inch heel, so for those looking for even more comfort, go for the Gianvito 70 instead. Just be sure to stick to suede, as it truly works year-round and is the easiest on the foot.
Black-and-White Striped T-Shirt
I have no idea why I spent approximately $300 on a striped T-shirt from Proenza Schouler many years ago, but truly it’s one of my most-worn pieces in my closet. Sadly, the brand isn’t producing it right now, but I found a pre-owned version on Poshmark, if you want to see it. That said: I do not regret it for a second. It’s tissue thin, the platonic ideal of stripes, and machine washable. And despite the fact that I’ve worn this piece probably 400 times over the last eight years (yes, I legit wear it once a week, at least), it still looks basically new.
Argent makes a much more reasonably priced version of my Proenza T-shirt, and if you’re open to navy instead of black stripes, La Ligne’s Davie Tee cannot be beat. (It also comes in a version that’s more white than navy, if that’s your thing.) Nili Lotan’s iteration is probably the closest option on the market right now, and I can attest to its quality personally.
Tailored Black Blazer
I’ve waxed on and on about A.L.C.’s brilliant outerwear options before, and I’m back to sing its praises once again. Designer Andrea Lieberman, the brand’s founder and creative director, understands a blazer like no one else. The shoulder is subtly strong, the fabrics are always classic, and the overall effect is completely sharp.
I have a black blazer from the brand that I probably bought in 2013 that is truly a wardrobe staple, and I’ve worn it with everything from my first-generation Current/Elliott boyfriend or bell-bottom jeans (circa 2008) to long silk slip dresses to ethereal-print skirts for the office.
A.L.C.’s Sedgwick II Jacket has a similar vibe and versatility (more sizes on A.L.C.’s website), and I like the brand’s Edie Jacket for a single-breasted option. With proper care, you legit will be able to wear either style for ages and ages and ages. I have a few other styles that are still in rotation and basically look brand-new, so trust me: A.L.C blazers are worth the investment.
Flat Tough Boots
As I’m pretty sure you know by now, I like my clothes on the trad femme side, which means I need to balance all that girliness with tougher pieces. Enter the best boots ever: Jimmy Choo’s Biker II Boots.
I’ve had versions of this exact shape for my entire adult life, and they last and last and last. Great with skirts and dresses (and tights in the winter), jeans or trousers, and even floaty white dresses in the summer, this style is classic but also doesn’t destroy your foot when you’re first wearing it. This might seem odd, but they’re actually my travel shoes of choice, and they only get better with age. Oh, and there’s a taller version of them and a short one too.
If you’re preppier and cannot abide by a buckle, go for a more equestrian style or even a classic Chelsea boot, which will get the job done too.
As a reminder: Last week I learned that the platform I use to create and send this newsletter—Bulletin, which is operated by Meta—is closing in a few months. While I’m sad that this is the end of the road for this first iteration of Hi Everyone With Hillary Kerr, over the next few weeks, I’m going to find a new platform, hopefully. (Substack? Ghost? Beehiiv? If you have a recommendation, please either leave me a comment or DM me at your leisure.) I’ll be able to bring all the past newsletter stories with me, so the archive will live on. You may have to sign up for the newsletter again, but I promise to share more details once I have them figured out.
While I’m looking for Hi Everyone’s new home, there might be a short hiatus in newsletter stories, but fret not. I promise they will be back. It has been an absolute pleasure and joy to work on this project and speak directly to this wonderful readership, and I’m truly honored that you all have made time for me and this newsletter.
As always, thank you for being here, and thank you for sticking around. If you have any questions or concerns, or want me to touch on any topics in particular, I’m all ears. Leave a comment on Hi Everyone’s Bulletin or DM me on Instagram—I’m @hillarykerr—my inbox is always open!