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actress katharine hepburn relaxes in stratford, connecticut, where she is rehearsing for shakespeare's merchant of venice with the american shakespeare festival
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Trends come and go, but certain looks never go out of style. Designed with longevity in mind, there are a handful of clothing and accessory items crafted with premium, high-quality materials, featuring classic silhouettes that can be worn forever without the fear of looking outdated. This not only makes getting dressed easier but is also better for your budget (there’s no need to buy tons of new items each season!) and the environment (keeping things longer means less waste). Below, Oprah Daily creative director Adam Glassman breaks down the nine items with sartorial staying power that every woman needs in her closet.


A tailored jacket

Whether paired with streamlined trousers for work or with jeans and your favorite tee, nothing pulls together a look quite like a tailored jacket. Clean lines and a structured silhouette have made the blazer a symbol of sophistication for decades—hello, Katharine Hepburn. “If you want it to last for a long time, look for a blazer with shoulders that are not too strong or oversize,” says Glassman. “A blazer should fit on your natural shoulder line.”

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Double-Breasted Blazer
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Carissa Two-Button Blazer
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A classic watch

“Watches are jewelry that are appropriate every day and for any occasion,” says Glassman. “Two-toned styles are the way to go, as they work with all your other arm candy. And yes, you can absolutely mix metals!” By investing in a quality watch, you’ll have an heirloom that can be passed down from generation to generation. Glassman notes, “My general rule of thumb: a good haircut, watch, and pair of shoes will take you far.”

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A button-down shirt

Repeat after us: Every woman needs a good white button-down shirt. It’s an effortless essential! “When in doubt, you can never go wrong with a white shirt. Period! End of subject,” asserts Glassman. “It’s the workhorse of your closet and can be worn casually, professionally, or even for evening.” Not sure how to wear it for a fancy event? Glassman suggests pairing it with a ball skirt. Unsure as to which fabric to choose? Cotton, silk, and linen are all quality options that tend to last the longest. Plus, you can’t go wrong with a version with some stretch in it—it helps with fit, wrinkles less, and is ideal for travel. Bonus tip: If you find gaping to be an issue, Glassman recommends purchasing a size up and tailoring the sides or adding a few small snaps between the mid-chest buttons.


Loafers

While loafers may be having a moment, they have always been in vogue. The shape and silhouette add polish and refinement to any outfit, whether your look is dressed-up or casual. Glassman notes that loafers are also not season-specific: Like the white button-down shirt, you can wear them at any time of the year. “If you take care of them well, loafers will stand the test of time. Plus, they will always come with great cost per wear because you will have them forever.”

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A cashmere sweater

While you may not be thinking about cashmere right now, a supersoft V-neck or crewneck sweater is the perfect layering piece that you can throw over your shoulders for unexpectedly breezy summer nights. Glassman adds that scoop or V-necks tend to flatter most body types, especially those with bigger busts. You can wear your cashmere sweater layered (think of lighter-weight options as alternatives to a tee) or on its own, day or night. “There's nothing chicer than a cashmere sweater paired at night with a dressy skirt,” says Glassman.

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Diamond stud earrings

Diamond stud earrings are a rite of passage for every woman—they hold significant value in terms of style and worth. Large or small, they look refined and classy paired with jeans and a T-shirt but can also add nice sparkle to a cocktail dress. And while this accessory is on the higher end of the price-point scale, Glassman notes that you really can find a pair for every budget. The larger you go, the more expensive a pair is likely to be, but a small pair can still look substantial in the right setting. “Diamond studs bring a lot of lightness to your face and will last for generations,” says Glassman. “You can pass them on to your children on their wedding day—or even your grandchildren.”

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A little black dress

The little black dress, often referred to as the LBD, has rightfully earned its place as a must-have wardrobe investment. To make sure it works for almost any occasion, it’s all about honing in on fabrication and silhouette. “Shop a fabric that has lasting power and wrinkles very little, like wool, gabardine, crepe, stretch cotton, or jersey,” says Glassman. “Then, choose a length and silhouette that suits your frame. Sheath, wrap, and A-line are all terrific shapes that can easily be worn professionally, for date night, or dressed up for evening glam. The goal is to find an LBD you love, and then style it with flats, sneakers, or heels.”

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A trench coat

A well-designed trench is an outerwear investment that has exuded sophistication for decades. With a long-line silhouette and belted waist, this style flatters all body types and is actually functional—wear it rain or shine! Glassman notes that outerwear generally is the most splurge-worthy category—but that splurging on a quality piece is worth it because it is the type of coat you’ll wear over and over. “They are entrance makers, and exit makers. They can make a look, or complement a look. A trench belted over leggings or skinny jeans and a tee or turtleneck is always in fashion.”

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A timeless handbag

“Everyone needs a great black bag that works for all four seasons,” says Glassman. “Before you purchase, be honest with yourself. A good rule of thumb is to ask yourself if you will wear it at least two days of the week. If the answer is yes, it’s a good buy.” Look for enduring styles (like a top handle, hobo, or crossbody) that have structure, clean lines, and are made from premium materials. Investment bags often have the advantage of retaining or expanding their value over time, making them both stylish and savvy purchases.

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Sara Klausing

Sara Klausing covers all things fashion and style for Oprah Daily.