I always have been and always will be an outfit repeater. In kindergarten, my family took a weeklong vacation to Jamaica, and I packed one pair of pants: yellow cargos from the boys' department at Gap. I wore them every single day of the trip paired with the only swimsuit I brought, which was a red Speedo one-piece. Almost two decades later, not much has changed—at least not when it comes to my proclivity to wear a select number of tried-and-true wardrobe items and then wear them a dozen more times with no shame.
These days, my tendency to wear the same things over and over has less to do with limited options and more to do with taste (and maybe a little bit of laziness). If I find something that I like that also fits me well and can be mixed and matched with my pre-existing sartorial regulars, I'm not just going to wear it once and then store it away until people forget. I'm going to get my money's worth by styling it in every which way that I can.
If dressing this way has taught me anything, though, it's that the pieces that do make it into your wardrobe rotation have to be versatile, season-less (for the most part), and fun to wear. After all, the goal isn't to wear the exact same outfit day in and day out but rather to wear the same individual pieces in a way that makes them appear different with each look.
Keep scrolling to find out which 37 essentials I repeat again and again.
An LBD like this one can be dressed up and down in a matter of seconds. It all depends on the shoes and accessories.
The second the weather tips above 60ºF, I wear poplin shirts at least four days a week, usually with a bikini and slouchy, cutoff shorts.
I love clean-cut jeans, but sometimes, only a distressed pair will do.
Knee-high boots are my kryptonite. No matter how warm it is or how low-key an occasion is, you can find me stomping around in a pair of tall heeled boots.
My favorite knee-highs are sold out, but these are giving them a run for their money.
It took me roughly five seconds of having this dress on to think up a dozen ways to wear it once I eventually made it mine.
I wear black trousers with everything: basic tees, waistcoats, a poplin shirt and tie, or even a corset. They're probably the most versatile item that anyone can own.
This style is versatile enough to be worn with both jeans and dresses. Plus, the padded strap makes wearing heels over and over much more bearable.
The great thing about sunglasses is that if you store them correctly, you could be wearing them for life.
If it ain't broke, don't fix it.
I'm not the type to switch out my bag for every different outfit, so I need ones that go with everything.
Because little black dresses never really go out of style, it's not a bad idea to buy a few of them. You know you'll get a lifetime's worth of use out of them.
I love pairing long jackets with short skirts. Maybe it's because I listened to that song by Cake too often in my formative years, but the combo is a classic for me.
Yes, I did buy this from the men's department. And yes, I do wear it every day.
Since I bought my first modern-day miniskirt, I've gotten more and more comfortable wearing the tiny silhouette. Once worried that I wouldn't wear it enough, I now wear my go-to miniskirt for even the most mundane, everyday tasks, like grocery shopping and picking up my laundry.
The easiest way to make an outfit look cooler with zero effort.
The ultimate luxe item that's actually worth buying.
On my last trip to Los Angeles from NYC, I didn't even bring a pair of jeans or trousers—just a single pair of leather pants, which I wore for much of my stay.
Celebrities and leather pants go hand in hand these days.
The concept of wardrobe essentials is different for everyone. For me, I like to have a few statement items on hand that can complement my more basic pieces. Case in point: this Prada-esque baby-pink miniskirt.
Every time my friends ask me which designer loafers they should buy, I always say these. They're classic and timeless, so you'll get way more use out of these than anything super chunky or trendy.
I hate waiting for occasions to wear my nice pieces, so instead, I find myself dressing up for no reason at all. It's better than great finds gathering dust in your wardrobe.
If there's one item to invest in this season, it should be an oversize leather jacket, period.
I know I'm supposed to stop wearing "lounge pants" and start dressing like a human again, but I'm far too smitten with these flowy, satin trousers to trade them in for something more structured.
I was never much of a sneaker person until I got a pair of Sambas by Adidas. I love that they're not super hyped up like other retro styles these days. Plus, they're super comfortable and easy to style.
Apart from boots, Sambas are my most-worn shoes.
These are easily the comfiest and coolest pants I own. Plus, they look just like the pairs Bella Hadid and Hailey Bieber keep wearing.
A top-notch blazer will take your wardrobe a long way, but plain black styles feel a little stale these days. To combat that, I'm frequenting styles in interesting fabrics like leather and croc.
Black jeans are as essential to me as blue ones, if not more so.
Tip: When you find a certain silhouette that makes you feel good—for me, that's tube tops—try to find more iterations to add to your wardrobe. The point is for you to want to wear every piece of clothing you own on a regular basis.
It takes touching this viral cardigan to see that it's actually worth the price. Heavy, baby soft, and perfectly oversized, there's a reason it's always selling out.
Shop the matching Vara Cashmere Bralette ($560).
Looking like an employee at The Row doesn't have to set you back hundreds of dollars. These tailored pants are proof that it will only cost $50.
Every single one of my friends has seen me wearing this waistcoat or one of the other four I own at least three times this season.
I wear this waistcoat at least once a week, mostly with matching or mismatching trousers but also with skirts and jeans.
Unpopular opinion: I like wearing clogs like these more than flat sandals in the summer.
When your swimsuit doubles as a high-fashion bodysuit, you know that it's worth buying and wearing as much as possible.
Under no circumstance do I take out my earrings, so I need a pair that will go with absolutely everything. These are just that.
I always hated having to constantly pull down my jean shorts because they were so short, so now that longer shorts are in style, I wear them constantly.
Every time I see this bag, I'm shocked by how much I still love it, even after carrying it 24/7 for almost a year. That's when you know you found a good one.
I have it in cream, which is sold out, but the black is next on my list. After nearly 365 days with it, I can vouch that it's 100% worth the price.
If you don't already own at least one trench coat, you're missing out. They're the perfect lightweight jackets for a look that screams, "I didn't try, but look how cool my outfit is."
One day, my entire wardrobe will be made up of just Skims basics. Where's Kim's award?
My midi-length denim skirt is one of my most-worn wardrobe items. In the winter, I pair it with fleece-lined tights and boots, and in the summer, it goes with flatform flip-flops or heeled sandals and an easy tank.
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