15 Timeless Fashion Pieces I’ve Kept in My Closet for 15 Years

I’ve been known to say “dress for the weather you want, not the weather you have” when defending seemingly nonsensical (or sometimes just idiotic) wardrobe choices. But over the past decade-plus I’ve come to really appreciate the utility of a good raincoat. I’m not talking about a lightweight jacket like what you might take on a hiking trip, but a chic coat that can be thrown over any outfit in any season and that is also waterproof, like a Barbour barn jacket or a Stutterheim trench. For me that coat is a black Burberry design with a removable hood and a fleece lining that can be zipped in or out. It was actually my mom’s, given to me temporarily on loan, however that “loan” has lasted nearly a decade, so perhaps it’s time I stop thinking of the coat as hers and start admitting it’s actually mine.

Owning stylish outerwear that can comfortably see me through inclement weather of any kind has been a true game changer for my rainy or snowy day outfits. It makes me feel infinitely more confident when leaving the house and like a posh adult rather than a kid in my yellow rain slicker.

Yes, this is highly specific, but with good reason. First, cashmere is always a good investment. It’s soft, breathable, ages well and is biodegradable. I’ll concede that a crewneck silhouette is perhaps not required—you could opt for a V-neck if that’s more your thing—but in my experience, it is the most flattering and versatile neckline for knits. As for the stripes? Black or navy stripes with white are about as timeless as a print could ever be and add more interest to any outfit than simple solids. They can also easily pair with almost any other printed item, be it florals or polka dots or even other stripes. I would venture to bet that I’ve worn a striped cashmere knit at least once a week for the past 15 falls and winters, maybe even springs too, and I’ll be shocked if that trend doesn’t continue for the next 15 as well.

Another somewhat specific item, these are the shoes I know I can reach for to feel comfortable and confident for any wedding, cocktail reception, work event or fancy dinner. Their minimalism is what makes them work with any outfit or season, and that short heel ensures I won’t need three days post-event for my arches to recover. They are the ultimate occasion shoe, a tried-and-true staple you won’t regret investing it.

Bet you didn’t see this one coming, did you? I’m not talking about “cool” sweatpants, or even flattering ones, either. I’m talking about a solid pair of well-made, comfortable sweats you can wear around the house to bridge the gap on days when comfort is your number one priority but you don’t actually want to stay in your pajamas all day. I actually have an entire section of my wardrobe dedicated to that brief window between the workday and bedtime, featuring these comfy sweats as well as oversize tees and soft bralettes. (I also find this helps my brain transition away from the day’s stressors when it comes time to go to bed—my “for sleep only” pajamas are a signal it’s time to start winding down.) But it’s really the soft pants that are the clincher, and that allow me to feel simultaneously comfortable but not schlubby. Fifteen years ago this was a pair of navy cotton joggers purchased from my university’s store and which lasted me for at least 11 years, but recently I upgraded to some Aritzia sweatpants free of logos.

Can you ever really have too many denim jackets? The answer is yes. At my peak I had 12 different jean jackets hanging in my closet, and it was approximately eight more than any one person could possibly need. However, a solid denim topper is an item I never want to be without and is without fail the little black dress of outwear. They’re the obvious pick for wearing over spring and fall dresses, look extremely stylish paired with jeans for a double denim ‘fit and give off an effortlessly cool vibe when layered with more unexpected items, like a wedding guest dress or office-appropriate suit. And it doesn’t much matter whether you opt for a classic blue-wash trucker, a black wash, a painter jacket, a denim blazer, a knee-length trench coat or a vintage acid wash—whatever style you’re drawn to most is going to be just as versatile as you hope. Plus, they’re almost always machine washable for easy care over the next 15-plus years.

New York’s summer humidity is brutal, and nothing feels as comfortable on those unbearably sweaty days as linen. My collection of linen dresses has evolved over the past 15 years, with the flirty A-line dresses of my early twenties getting swapped out for elegant, strappy midis and ‘60s-inspired, swingy minis. But every year when those temperatures start to rise, I’m grateful to have a series of easy, breathable frocks I can rely on for any occasion.

In much the same way that drywall is the boring-yet-immensely important material giving structure to your home, the plain white tee is pretty universally uninteresting, and yet essential to any wardrobe. It’s the epitome of simplicity, a literal blank slate on which to build outfits of any aesthetic or style. Confusingly, the perfect basic T-shirt also an item many would call elusive. Mary-Kate and Ashley Olsen claim to have started their fashion line The Row with the explicit goal of creating the ultimate plain white T-shirt, such was their disappointment with what the market had to offer at the time. So whenever I stumble upon a tee that fits me to a T, I make sure to pick it up in black, gray and white, knowing those tops will be well worn and loved until they start developing holes…and even for a while beyond that point.

I must confess, I didn’t get my ears pierced until I was 27 years old. But since then, I’ve come to wear gold hoop earrings more than any other style I own. Specifically, I wear these wavy Missoma hoops on a near daily basis, but more classic variations are also on heavy rotation. They’re the ideal everyday earring—more noticeable than studs, but not quite as attention-grabbing as a dangling statement earring. Of course, hoops have a long history within the Black and Latinx communities making them much more than just a “wardrobe essential.” They are a reminder that fashion is almost always more than just fashion, and of the importance of how we connect with clothing and accessories.

There was a time when I could not travel anywhere without my white canvas Keds. Then I was gifted a pair of white leather sneakers from M.Gemi, which were just as versatile and far more practical for the colder months of the year. These days, it’s a pair of Dolce Vita kicks that have me in a chokehold. But no matter which variation you lean towards, a pair of simple white sneakers are a fantastic all-around shoe that’s also comfortable. Especially since 2020, many of us have decided uncomfortable shoes just are not worth the hassle, so that comfort component is super important when choosing your go-to sneaker. And while there are always new brands coming out with cool new comfort-focused kicks, this is one item for which I’ll almost always recommend the old standbys (Nike Air Force 1s, Adidas Stan Smiths, Keds Canvas Champions) as the most enduring options.

Denim trends will come and go, but a classic straight leg in a medium blue wash will never be a bad choice. Whether you prefer a high, mid or low rise, a button or zipper fly, or something with a distressed hem rather than a clean finish, all those specifics are up to you. But the two key elements of a truly timeless pair of jeans are a leg that’s just a little loose and that falls straight down from the hip to the ankle, and a medium wash that’s neither too light nor too dark nor too blue. I’d also recommend avoiding distressing, whiskering or over-the-top pocket embroidery to really ensure those evergreen vibes.

I was in high school the first time I tried on a Tissue Tee from J.Crew. The experience launched a decades-long love affair with the thin turtlenecks, one that I don’t anticipate ending any time soon. As J.Crew’s designs changed over the years, I’ve branched out to include other brands, like Splendid and Intimissimi, but the core elements of this beloved wardrobe staple remain the same. The fabric must be thin and lightweight enough to easily layer under anything and everything, and the cut must be slim but not body-hugging. I’ve worn these beauties under cozy knits for an extra dose of warmth, under band tee for an edgy, punk-inspired vibe, with a red lip and ladylike jacket as a Parisian cosplay and on their own tucked into tailored trousers and dark-wash jeans for a streamlined ‘fit. They are the second most-worn tops in my rotation after that deliciously boring white T-shirt.

Belts are having something of a moment in 2025, but my go-to black leather belt has been in my closet since my very first internship after college and was a well-worn part of my accessory rotation long before the trends shifted. The reason for its enduring appeal is really very obvious—sometimes clothes fit differently from when we first acquired them and a belt can help fake a more ideal fit. I have jeans that have stretched too. Much in the waist and hips that still look great with the addition of a belt, and dresses that feel a little shapeless and blah unless cinched at the waist. A simple leather belt in a neutral hue like black or dark brown, can be deployed to zhuzh up any number of outfits without drawing any attention to itself. Hot Tip: Opt for a belt that fits well around your hips and ask a cobbler to add extra holes so you can wear it around your waist as well, to get more bang for your buck on a timeless investment piece.

OK, they don’t necessarily need to be Tevas, but practical sandals—by which I mean a pair that doesn’t give you blisters, can survive a sudden summer rainstorm, and that have even a modicum of arch support—are a must-have, in my opinion. I’m personally a devoted fan of Teva, having worn the Original Universal style since elementary school and recently adding the Olsen-approved Infinity to my collection. Both styles are comfortable for long periods, even while walking around the city or hiking, and are designed to stay sturdy and dependable when wet (an obvious plus for hiking, but surprisingly handy in the city too). I decided years ago that I am officially done with flat, rigid sandals that offer no support and very little protection from the grime of NYC sidewalks. There are, of course, brands other than Teva that fit my rigid list of requirements: Chaco, Keen and OluKai are all excellent options, and more than one PureWow editor swears by Birkenstocks.

Another fairly specific wardrobe item I swear by is the black silk cami. My preferred camisole is from Cami NYC and has lace straps to add a little extra something-something to the design, but a super-simple version will serve you just as well. I wear mine under pullovers to prevent itching, under cardigans for the office or on its own tucked into a pair of jeans as a supremely classic going out top. It’s a top that has been, at times, the It look of the season, but that never feels dated or truly out of place. It also looked just as cute and age appropriate when I was hitting up dive bars at 22 as it does now hitting up slightly more posh cocktail bars at 34. And while I’ve certainly owned other colors too, like nude for better layering under light colors or bright red for a bolder impact, it’s the solid black that I’ve returned to time and time again for the last 15 years.

There is no capsule wardrobe that truly fits every person. I swear by sweaterdresses and knee-high boots, but many of my best friends won’t wear either. The true delight of crafting your own capsule wardrobe is in finding those unique pieces that you use all the time, even if they wouldn’t make a lick of sense in someone else’s closet. For me, those odd additions that actually get a ton of use include a pair of green slingback flats with enormous bows on the front I’ve had for five years, a striped purple sweaterdress from H&M I’ve owned for 13 years and a beige cardigan sweater with books printed along the trim from J.Crew I’ve been wearing for a whopping 17 years (though it’s really starting to show its age).

The item I’ve owned for the longest period of time and that I also wear on the regular is a necklace given to me by one of my best and oldest friends, Lisa, for my sixteenth birthday. It’s a simple trio of gems oriented in a vertical line and strung on a dainty silver chain. It is the very definition of heirloom jewelry: timeless, elegant and deeply meaningful. It’s also an ideal example of why I never part with jewelry, if I can help it. These pieces take up so little space and even if your tastes change over the years, nothing brings on a flood of memories and emotions quite like holding or wearing an old piece of jewelry.