Believe Me—You'll Still Want These 36 Items in 2026 (and '27 and '28)
There's a time to shop for trending items—aka pieces that will only really work in your wardrobe for a season or two—and a time to invest in timeless, forever staples. A party with a very specific dress code or theme falls into the former category, while a designer handbag or pair of classic jeans would go in the latter. If what you're buying has a short shelf life, don't spend real money on it. What's the point if it'll become useless in a few months?
So, when it comes time to introduce pieces to your wardrobe that you plan to still own and wear one, two, or even 10 years from now, that's when it's smart to devote a significant chunk of change to your purchases. It's all about price per wear, and donning something multiple times a year for many years will essentially make even your biggest buys free. (Girl math?)
To help you decide what you want to spend your hard-earned money on, I went ahead and rounded up 36 timeless investment fashion items that I guarantee will continue to get regular wear for at least the next decade. There are designer-brand icons, like the Dior Bar Jacket, The Row Margaux bag, and Cartier Tank watch, as well as new arrivals that I'm predicting will reach cult status with time, like Tory Burch's new large Lee Radziwill shoulder bag and Khaite's Winslow jeans. Intrigued? Keep scrolling.
If I were to invest in one fall outerwear piece in 2025, it would be this suede bomber jacket from Saint Laurent. Easy.
Eliza Huber is an NYC-based senior fashion editor who specializes in trend reporting, brand discovery, and the intersection of sports and fashion. She joined Who What Wear in 2021 from Refinery29, the job she took after graduating with a business degree from the University of Iowa. She's launched two columns, Let's Get a Room and Ways to Wear; profiled Dakota Fanning, Diane Kruger, Katie Holmes, Gracie Abrams, and Sabrina Carpenter; and reported on everything from the relationship between Formula One and fashion to the top runway trends each season. Eliza lives on the Upper West Side and spends her free time researching F1 fashion imagery for her side Instagram accounts @thepinnacleoffashion and @f1paddockfits, watching WNBA games, and scouring The RealReal for discounted Prada.
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