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Women went nuts when Donna Karan launched DKNY in 1989 as the young, contemporary counterpart to her high-end Collection line. And with good reason: At a time when dressing for work largely meant boxy power suits, Karan offered stylish, energetic and flattering pieces that could be combined in tons of different ways, quickly establishing herself as the unequivocal master of on-the-go, city-girl style.
“I started DKNY with basic essentials,” says Karan—a simple jumpsuit, an anorak and a solid black dress among them. “The idea was to have affordable clothing you could mix and match and have fun with; the energy of it was completely New York.”

Twenty-four years later, the designer is hotter and more successful than ever. DKNY now includes men’s, denim, accessories and fragrance branches with stores around the world and collaborations with edgy labels, most recently Opening Ceremony (which did a capsule collection of reissued DKNY ’90s staples, including logo tees and bodysuits). Yet Karan’s brilliantly simple design approach remains unchanged. Whether she’s re-creating her trademark windbreaker in bold primaries, inventing wrap sweaters that can be worn 12 ways or covertly slipping slimming bodysuits into the flowiest dresses, she consistently comes up with fresh ideas to fuse functionality with adorability.

The brand, she explains, has always been about embracing everyday life. “DKNY is timeless,” says Karan. “It’s based on something real. It’s not based on some kind of fantasy. It’s like a pair of jeans—it’s functional fashion.” And it’s always so much fun.
1. Bodysuit
“It’s all about the tuck-in factor. With a bodysuit, even if you wear your pants sloppy and low, you’re still clean on top.”
2. Anorak
“The anorak has been a DKNY essential since the beginning. It’s the idea of her wearing his clothes, and there’s something so sexy about that.”
3. Belt Bag
“We’re constantly in need of our cell phones, but who wants to carry a purse all the time? Just throw all your stuff in a belt bag and you still have your hands!”
4. Printed Jeans
“Printed jeans in browns and whites and blacks—how amazing? They’re neutral, so you can wear them with everything.”
5. Yellow Dress
“Every girl needs a work-to-beach-to-night dress. This one is not at all fussy, but it’s completely showstopping.”